The Madonna Deep Dive: Underrated Hits & Confessions II Anticipation with Tranna Wintour

0:04 Hey everyone, so welcome to the Bunda Me Chronicles Podcast. My name is Randy Kim, and I'm your host. So I am bringing back a familiar guest. Her name is Trana Wintour, and I have been a big fan of Trana for quite some time now, starting from when she was a guest on the MLVC Podcast, which is the Madonna Luis Veronica Ciccone, which is short for that name. I have always loved her takes on Madonna, especially more recently with her Instagram, Trana Wintour, where she shares some of her current perspectives and whether they're popular or unpopular takes.

0:45 And Trana has also, you know, has been a comedian. She's an internet and TV personality. She hails from Montreal, Canada. And I just want to say, well, welcome back to the show. How are you feeling about the recent Madonna teaser for the Confessions 2 album and her Coachella appearance? Well, hello, and thanks for having me back. This is a pleasure. And I mean, I want to be really excited. But, and there's a, I mean, there's a lot that I am really excited about. Like, I love the direction that this whole project is going into.

1:28 I really am enjoying. I feel so free. Like, I don't think it's, like, mind-blowing, but I really enjoy it. Like, I've been listening to it on repeat. Like, I'm vibing with it. But I feel like I'm keeping my expectations low. um maybe just because I don't want to be disappointed because this is such a big project and it's her first album in like what seven almost seven years yeah so yeah I don't know I'm keeping my expectations in check but so far you know like it's looking good I think it's looking a lot better than Madam X and like I had mixed feelings about the Coachella thing like You know, I hate to say it, but like Madonna's just not the same person anymore.

2:22 And it's not an age thing necessarily, you know, because I saw Tina Turner on her farewell tour when she was 69 years old, which is two years older than Madonna is now. And Tina was still... HERSELF AND LIKE YOU KNOW EVEN IN AND I'M NOT SAYING THAT MADONNA HAS TO MOVE IN THE SAME WAY THAT SHE USED TO MOVE UM BUT YOU KNOW TINA STILL HAD THIS POWER THIS FORCE WITHIN HER AND I DON'T FEEL THAT POWER FROM MADONNA ON STAGE ANYMORE LIKE I FEEL LIKE YOU KNOW WHEN I WATCHED HER AT COACHELLO LIKE IT WAS FINE IT WASN'T BAD BUT I JUST I'M LIKE SHE DOESN'T HAVE THAT COMMAND ANYMORE BUT SHE IS KIND OF GONE AND I It's like I almost don't even want to say it out loud because it kind of breaks my heart to admit that, you know?

3:10 Yeah, you know, I kind of see it from a different angle, but also I felt like with Celebration, the Celebration tour that was a few years ago, I was very happy that she was finally starting to embrace her legacy, which she has avoided time and time again. I mean, I would go to concerts and I'm like, Man of X tour being one of them, like, why am I hearing Portuguese cover in the middle of the night? Like, this is not, this is not my This is not ideal for an evening to be listening to Madonna where people don't recognize most of her songs except her hardcore fans and I'm like okay this is not doing anything you're making people stay up till midnight for you to get on stage Yeah and then just kind of leave very underwhelmed and so like I felt with Celebration there was life even though her dancing was significantly slowing down I mean yeah no I loved the Celebration tour and I felt I felt that power on the Celebration tour like I felt it you know like when she you know came on the stage opening with Nothing Really Matters like I remember I went two nights the first night I mean I think I cried both nights but that first night it was like the first time and in a really long time that I had seen her on stage because I've basically been to every tour since Reinvention except Madame X so it had been like you know a while since the last time I had seen her and I felt that power at the Celebration Tour but I did not feel it watching this Coachella performance like I don't

4:42 I don't know like again I don't want to veer into like guessing what's going on with her but like she doesn't seem very mentally present there's something off like I don't know if it's some sort of substance abuse thing like or I don't know if it is if maybe it is just strictly age I don't know but she doesn't feel all there to me and maybe I'm wrong and I'm happy if people are experiencing it differently but I don't know there's something I don't know to me she's just not the same person anymore yeah no I hear what you're saying too but you know also like I mean I look at Mariah Carey now she oh Mariah it's the same thing but you know but worse actually it's even worse yes I agree that it's even worse but like there is you know when I saw Mariah at the Olympics which was like really sad to watch And I agree that that was worse than the Coachella performance, but there are similarities.

5:39 And I, I mean, I suspect that like Mariah is very heavily medicated. And, and again, like, I don't want to speculate on these people's like medical conditions, like who am I to speak on that, but all to say is just that there's something off. There's something not fully clicking you know like even Cher for example like Cher is almost 10 years older than Madonna and like you know her her movements have become stiffer and her voice is not exactly what it used to be but her energy and presence are still there she's still Cher yeah This doesn't feel like Madonna to me like there are glimpses of Madonna Madonna that I know and really was attached to for so long and I still love her don't get me wrong and like her music still occupies an enormous space in my life and she's still the artist that I listen to the most and music means and will always mean so much to me.

6:36 Yeah But I feel like I guess I'm just making peace with where she's at and I'm just trying to meet her where she is instead of like having expectations based on her immaculate career Yeah I think the reason why I felt more refreshed I think the last 10-12 years since the Super Bowl halftime performance in 2012 I felt like she was trying so hard to chase after young people like she was trying to compete with the Lady Gagas and Miley Cyrus and I felt like this is very cringy to watch and I felt like What are you doing Madonna like you are a trendsetter you do not need to get their validation like they need to come to you and I felt like with the Coachella performance I felt like she came out and she looked beautiful and I felt like she came in um on Sabrina's stage and with Sabrina's blessing instead of having to her take over the stage and but I also felt that Madonna was probably very insecure because I did see a lot of nervousness which is exactly which was very that's not Madonna no it isn't because from the first note like yes it was great to see her coming out and but the way she was kind of moving I felt like she kind of needed to be guided But you hit the nail on the head.

7:58 It's a confidence thing. Because again, to me, it has nothing to do with her age. It has nothing to do with her ability, her physical ability. She could literally be in a wheelchair and still possess that magic. But that lack of confidence, like the magic is in that confidence. It's in that, it's when she is connected and aligned to her power and it didn't feel that way to me. And Like I don't know if it was something going on in her monitor but like her lip syncing was always like a second off and like it I'm like this is I mean it's not as bad as that infamous Maluma performance a few years ago but but you know but the thing that you're talking about like from the sort of halftime Super Bowl show um and those years afterwards like chasing This sort of mainstream relevance and like trying to appeal to a younger audience when it's just so unnecessary, like, I kind of feel like she's still doing that, you know, like, I agree like she looked beautiful, though I'm not crazy about the styling, like, I'm tired of her always being Bánh bánh bánh bánh bánh bánh bánh bánh bánh bánh bánh bánh bánh bánh bánh bánh bánh bánh bánh bánh bánh bánh bánh bánh bánh bánh bánh bánh bánh bánh bánh bánh bánh bánh bánh bánh bánh bánh bánh bánh bánh bánh bánh bánh bánh bánh bánh bánh bánh bánh bánh bánh bánh bánh bánh bánh bánh bánh bánh bánh bánh bánh bánh bánh bánh bánh bánh bánh bánh bánh bánh bánh Yeah,

9:28 I mean... And also, I think it's very interesting because when we see the Coachella performance, we see, like, the people with their camera phones. Oh, God. It was very dystopian, too. I'm kind of like, what is going on? I'm like, I'm guilty of, like, recording, but I also have, like, a... But also just the lack of... The lack of enthusiasm for this legend that is on stage Yes Like I'm sorry she's like basically one of three living legends who are still alive It's like people you guys gotta wake up like I blame that on Gen X's parents for not doing the job of raising the kids. Y'all were raised on Madonna.

10:09 How can you not get away from her during MTV? Exactly. This is your job to be teaching them. It is, but it's also like I just feel like it's kind of impossible just because the culture has changed so much and like these kids are on their phone and they're only being fed what the algorithm shows them and if they don't have the curiosity to go beyond the algorithm they're not going to find it whereas like when we were growing up we were kind of like Not forced but like we were kind of shown everything because there was no other option it was like you had to sit and listen to the radio or watch MTV for like an hour just to watch the one thing you wanted to see and in that time you were being exposed to so much you know like when I was 12 I knew who Barbra Streisand was I knew who Bette Midler was like but it's because like I used to watch Entertainment Tonight every night and like you just would learn about things but now it's like there's not that sort of natural learning It's unless you're seeking it out, like you're not going to know about it.

11:13 And that's kind of depressing. I think the depressing thing is not the way that media operates, although there is an element of that. I think what's sad is just that the kids don't have curiosity. They're not curious about the past. They're not curious about the things that came before them. And I find that alarming. Yeah although I will say like I think maybe the devil's advocate is I have seen some cracks in the foundation like where I'm starting to see like actually I have a good friend who's a diehard Madonna fan his son who is also a queer person who's like I believe like a freshman in college is a diehard Madonna diehard Celine Dion fan Okay I know there are some And I'm like yay and also like there's certain people that want the physical media because that generation has like Like they want the vinyl, they want to get the cassettes and the CDs because they want to feel something.

12:07 Yes, I've noticed that too. Yeah, like I'm a big like, like I love like physical media. So like I go thrifting a lot like for CDs and vinyl. And I've been noticing like everywhere I go now, there's so many like people that are like 25 and under that are like shopping for the same stuff. And I love seeing that like that makes me happy. Yeah, so I want to get into what I think is the top 10 underappreciated, underrated Madonna hits songs. Now, some of these songs have been big hits before in the past, but have kind of been forgotten over time. Some have been kind of like a deep cut or two.

12:51 So it's like... I want to be more contextual about like okay these are some of the songs that I think about I mean does it change I mean to find 10 Madonna songs that are underrated or the best Madonna song is a gargantuan task I think it took me quite a while I think by the time I schedule this interview with you it's like weeks in advance and I'm like okay this is going to be a challenge that I'm not that I'm going to have to take on so yeah so this is what I came up with so I'm going to get your reaction I have For number 10, Intervention from the American Life album. I love the American Life album. I think that album is severely underappreciated because of what happened with the Iraq War and her having to cancel out the American Life music video, which I thought was as painful and traumatic as it is.

13:40 It is a work of art. Yes, it is. And I felt like that was a missed opportunity. And unfortunately, because that did not take off the rest of the album didn't and that was a shame and I thought Intervention was one of those songs that I felt like she didn't really spend enough time playing live and I felt like this is like one of her best mid-tempo ballads it's such a good song I love it too I mean she did it on the Reinvention tour so at least it got some got some light shone on it I also love this song I agree with you about American Life I think it's a really great album that album probably has like the The most concentrated amount of like underrated gems I think of also Ecstatic Process which to me is like one of Madonna's most beautiful songs and it's like probably her most stripped down song like it's this really rough acoustic guitar and just her vocals and it's so beautiful but yeah Intervention is a great choice I think it's a great great song that whole album I think is really worth visiting It's interesting like I agree with you about the video but I also wonder like there's a part of me that thinks that even if the video had gotten released like I don't know if the album would have been such a success because it's such a strange album like music sort of introduced this idea of like her doing Folktronica and it really worked but like I feel like American Life took it one step further and it

15:11 became even a bit more avant-garde and like kind of harder to access like for a mainstream audience. So I don't know if I don't know if there's any scenario where the album would have done really well just because I feel like it's not super mainstream like it's really like the production is so strange but really interesting you know but usually the strange interesting stuff doesn't tend to connect with like a mainstream audience. Yeah and I think that really hits to a good point there because Like even the single like even though the video was great like American Life is a weird ass song Like I love it but it is a weird ass song And also I think that around that time, and I think she was already doing this for a while, you know, she was like going into her motherhood.

16:01 She was stripping away from the sexuality that was like very much dominant in the 80s and a good part of the 90s. And so I felt like she was trying to put the reset. And I think after that album, I think she's realizing, okay, I don't think my audience really wants that, which obviously led to confessions, which Basically turn the script upside down. And so I think that when I think of the intervention, I think of it as like a spiritual cleanse. And this is what I've noted down, like the ending of that song, especially in the last 30 seconds, where it's just the guitar and the drums. It's very cathartic.

16:42 And I feel like I just love the way it ends. And that's something that really feels... Like it gives me a bit of a lift and probably one of my favorite ballads on that album. I mean, I could pick Easy Ride, I could pick a bunch of others on that and I'd be fine. So the next one, number nine, Bedtime Story from the Bedtime Stories album in 94. Now, this was a song that was written by Bjork, Nellie Hooper and Marius DeVries. It was also like in a way a precursor to Ray of Light years later. If you like notice the sound and the direction she was going in musically and Madonna was a big fan of Bjork's debut album and you know I'm a big Bjork fan myself and but not surprisingly Bjork was not a fan of Madonna's music and I think in an MTV interview she was like well I don't really know her this was a gift to Nelly Hooper and but she also like wrote it based on what she always wanted to hear Madonna say Which I think that's very interesting because Bjork is a very esoteric, very cerebral, she goes into abstracts in ways that Madonna doesn't perfect.

17:55 So I feel like Madonna tries to go there but Bjork has always been in this direction I think well in a way like hearing you talk about like describing Bjork that way like I think American Life is like Madonna's most esoteric and like most like you know avant-garde album in that sense and it's interesting like the connection between Bjork because for the American Life album artwork she used MM Paris which are the guys who do all of Bjork's like graphic design and art direction so like there's a connection there mm-hmm and this is a song that peaked at number 42 on the Billboard Top 100 which was considered a disappointment at the time because it was the first song to not hit the top 40 since the beginning of her career so I think the reason why was because it was too considered really out there it was very experimental music video was It's very iconic and also really one of the most expensive videos ever.

18:52 So I think when you hear that song, it's like, okay, is this a song that you can really dance to at a club, you know? Is this a song? Well, you can dance to the remixes. The remixes are so good. I love the remixes. Yeah, and I just love the futuristic vibe of it. I mean, that video is such a trip. I feel like it doesn't get enough love I think it has always been forgotten even though I do think the music video itself is probably one of the best Madonna music videos ever dare I say it well not just one of her best videos like one of the best videos Period of any artist it's incredible that video it's stunning it still holds up it's still mesmerizing and I agree with everything you've said like it's one of my favorites too like I love the song so much um I even like spent way too much money on getting the 12 inch single that has the like metallic holographic cover like I'm so obsessed with everything related to this release I love the remixes I was so happy she did it on the Celebration Tour because like you said it deserves to have some attention and I love that she gave it some attention and I think the performance of it on the Celebration Tour where she's on top of this giant video cube was sort of reminiscent of the video and the sort of surreal aesthetic of the video and the futurism of it all it was one of the highlights of the tour for me and she also did it as a video interlude on reinvention so like you know I think it's safe to

20:26 say that this is a song that she herself loves a lot and feels is underrated too yeah and I think the album itself tends to get slapped on quite a bit and I think it's probably like one of her least played I mean, she doesn't really play a lot of her songs from that album in concerts. Well, with the exception of Human Nature, which she's maybe done too many times. Yeah. Although I love, although Human Nature is really one of my favorite Madonna songs. There are times I'm like, okay, you really don't need to put this one out there, you know? No, exactly. Because it's like, you know, a Madonna tour is really special. And because her catalog is so enormous.

21:08 Yes. It's like you want every tour to highlight different songs. So like when she does Human Nature on like five tours back to back, it's like, okay, we get the point. We get the point. Exactly. How about bringing in Candy Shop? Well, don't even get me started on that. I have to admit, okay, a hot take would be like, as much as I cringe looking at Candy Shop on the set list, I'm like, it actually sounds really good live. I know, I'm not gonna lie, it does work live. It does work live, but I would never listen to it on album. But at the same time, no, at the same time, like, please give us something else. Which brings me to a song that she has never played live, which I'm still extremely angry about to this day, Rescue Me from the Immaculate Collection.

21:53 This is a song that, again, she has never played live. She was about to tease that for the Man of Mechs tour, but instead we just got a spoken word interlude and that was it. And I'm just like, you were teasing this. You've acknowledged that that song hasn't been played live. And I'm thinking that this was going to be a highlight of Man of Mechs, but no. And I've still kept a grudge on that. I haven't let go of it because I think it's such a powerful song the spoken word um um Take that she does with the song is also like on par with Justifying My Love, which is also on the Immaculate Collection around that same time.

22:36 So it really fits into this specific window that she was really kind of going into, which would lead to erotica, which is more like a half singing, half spoken word in a way. I think also very avant garde in some of its way when it comes to house music and and a different pop landscape that she was traversing in. But yeah, this song did peak at number nine. No music video, surprisingly. No live promotion of it. I just think about the Gospel House song, which harkens back to like a prayer, you know? Yeah. Yeah, what are your thoughts on Rescue Me? Well, I love it, too.

23:16 One of my favorites as well. I wonder, like... Sometimes I'm amazed at some of these songs that actually charted so high but they were like never really played on the radio like I don't think I've ever heard Rescue Me on the radio once in my life and I don't think it's a song that non-fans have ever heard of so it's it's so interesting that it managed to still peak at number nine despite like being kind of invisible but yeah I love I mean she She loves a spoken word moment. I mean, even on I Feel So Free, like there's kind of a return to this sort of form for her. So like to me, I Feel So Free feels very much in line with Rescue Me and Justify My Love and Erotica.

24:00 And I mean, there are so many non singles that also feature spoken word like Waiting and Secret Garden. And she has a great speaking voice. And there are so many songs like that will feature even just like spoken word, like little bits, little moments. So like, I love a Madonna spoken word moment. She has such a sexy voice. I feel... I just love her speaking voice a lot me too it's like powerful and not everyone can pull that off yeah it's very cheeky too and it's very seductive it's very seductive and I can't get enough of it I mean I could like quote truth or dare any time of the week you know because I love that film I love the way she gets very very Like toys with reporters and the way she like really, really gets into her moment or when she gets into her Dita, her alter ego during the days.

24:59 I mean, I think that that really speaks to the mystique and the aura that she's trying to create. And I think it really works. It really works. And it creates a kind of intimacy, the spoken word, you know, like it's, yeah, it draws you in. And I would also say Rescue Me also has amazing remixes. And very fortunately, most of Madonna's maxi singles are on streaming so people can go and listen to all of these remixes. And I mean, I've always loved remixes, but Rescue Me especially has some really good remixes. Yeah, you know, it's a nerve really good. I know you're a big fan of ballads. Next one for number seven.

25:40 Lift the Toe from the True Blue album. This was done in 1985, I think right before True Blue came out. And this was for the soundtrack that her then husband Sean Penn was in at close range. Personally, I think this is easily her best ballad. It is very haunting. It is very confessional. It's probably one of her first major ballads if I'm not mistaken. And this kind of like represented a different turn in her career because like the Mì Bites type of voice maybe like I think I'm Going Bananas is one of them I think maybe that's yeah that's the last that's the truly last one but it is an exception for sure yeah and I think that was so unserious it was very stripped down it was very much a song that I still resonate to this day and I mean I've seen her perform that song a couple like I mean I know she's performed it for um Who's That Girl Tour then Blonde Ambition and then to Confessions which I saw that and then last tour for Celebration which was very beautifully done when she gave the dedication to people who were lost to the AIDS crisis and I

27:14 think that was probably one of the more powerful moments of that show and honestly I think that's a song that really gets overlooked and it was one of her I think number one hits songs but I think it's a very enduring song it feels very timeless I go back to it every time I hear that song in my playlist like I feel like I have to be in silence yes it's so meditative it's So powerful. Again, I totally agree with everything you've said. I, you know, if I really had to make this choice, I would say this is her best song in her entire catalog. I think this song, I mean, I know that Like a Prayer tends to get that kind of recognition and it also deserves it too.

27:59 It's very up there. But there is something about Live to Tell that is just... This is her most soulful, most beautiful, that emotional depth that you're describing. I mean, it's there in a lot of her work, but I feel like it's here on a totally different level. And even though it was a really big hit, like it was number one. I do feel like it's one that the general public is a little bit less familiar with but I think that this song is an absolute masterpiece like I on New Year's Eve I went on like a little mushroom trip and I put this on the playlist for like the end of the journey and Like hearing music on Mushrooms is like such a different experience it really allows you to sort of like live inside the song like I can't even fully explain it but it's like it just everything sort of hits on a different level and when this came on and I listened to it in that context it truly astounded me you know and even though I've heard the song a million times like that night like I just heard it in such a different way and like I mean this is gonna sound a little shady but I'm like how can someone who's so fucking evil make something so beautiful yeah Because this song is exceptionally beautiful.

29:27 It is. It is spiritual. It's vulnerable. If it comes on, you have to take that time and silence to live in it for the time that it's playing. I don't even have the words to fully express just how deep and beautiful and moving and powerful the song is. Yeah. You know, the lyrics are so powerful and beautiful as well, but they're all so vague in a way that this song can take on so many different meanings. Mm-hmm. It could be... Yeah, because, I mean, it could be, like, if you dealt with child abuse, if you dealt with domestic violence. I mean, I think that those songs, like, resonate on a level of trauma that it kind of...

30:08 That it really seems to hint towards, you know? Yes. I know she was also married to Sean Penn, so it's not ironic, too. But I also... I think about how that song really changed the way she saw her career moving forward like I also wanted to be a serious artist I want to be a person that's not a flash in the pan I don't want to be like a Cyndi Lauber and that's no shade to Cyndi Lauber I think she's brilliant but I feel like she was really trying to like Take on a whole new direction, a whole chameleon-like presence. Like, yeah, I'm more than just a boy toy. Now I'm actually a balladeer. Yes, exactly. And I, you know, like, I have a good friend of mine who's also a diehard Madonna fan, and sometimes we, like, We give each other these sort of like ridiculous challenges where either it's like choose a song that is you know if you can only listen to one more Madonna song for the rest of your life what would it be like we we love to ask each other these kinds of questions and one time I remember asking him it's like okay like for the rest of your life you can only listen to the Madonna ballads or the Madonna dance songs and I chose I and I still choose the ballads I think she is an incredible balladeer mmm I agree and like you know actually the first Madonna album I got was the something to remember which is the ballads collection that was one of my early albums that I got as well and I'm still obsessed with that album and even though it's a compilation it

31:38 really plays like a studio album it's so well put together And even just the cover art of Something to Remember is just so beautiful. I could just stare at that picture of her for hours. Oh, I love it. That's iconic. Underratedly iconic. Yeah. Also, a little random side note. I recorded an album a few years ago. A version of the album is on streaming but because I did some cover songs and so some of them are like if you mash things up together it's like really hard to get the rights whereas like if it's just a straightforward cover now it's really easy with like all the different like distribution services but basically like I did a cover of Live to Tell and I mixed it with Frozen and it's really interesting how those two songs are so similar they actually really blend together and obviously Frozen was also co-written with Patrick Leonard who also co-wrote this with Madonna so like there's also a parallel with Frozen and I would also say like the last thing that I'll say about Live to Tell is just that like and this applies to so much of Madonna's catalog in general like so many to this day and the same thing happens with Mariah Carey but I think it happens even more with Madonna is that people really do not understand how unbelievably talented she is as a songwriter and when you go back and you look at the credits of these songs including Live to Tell it's literally just her and one other person who wrote it

33:08 you know yes it's like she really wrote these things these are not just she didn't just slap her name on the song like She wrote these songs and I think it's super impressive and I don't think she'll ever get the credit she deserves for being the songwriter that she is And the New York Times didn't give her that credit but not that I care about the New York Times for a number of reasons What number of reasons exactly but like but Madonna I will die on that hill Madonna is an amazing songwriter Absolutely I mean also she knows how to make the most vapid shallow songs really work I mean she makes the greatest melodies like Into the Groove like when she had to throw out the word live out your fantasy here with me I'm like okay this is such a great bridge and I'm just like it is and like even though like Into the Groove and other songs like might on the surface seem more disposable they're not like they really they really contain a power and a magic they sure do and Which brings me to the next song Angel from the Like A Virgin album Now this was like the A side and the B side was Into The Groove which it's kind of unbelievable how that was marketed because Into The Groove was seen as a B side singer and I'm like how is that possible with that kind of Mì Bites Mì Bites Mì

34:39 I mean it's one of my favorite early Madonna songs there's no music video for that one I don't think she's ever played it live except maybe the Virgin tour and I feel like that song has been kind of like disposed of over the years but yet it is a really good song and just kind of gives you like the innocence like the very cheery Madonna vibes that really attracted the young girls you know it's like it's a very It's a very joyful and innocent song that's very much like I'm sure was back then a staple in high school dances.

35:21 For sure. Can you imagine? Yes. Yeah, this is a great one. I don't know if it's one of my big, big favorites. I think I went through a phase with it like when I was like a teenager where I really was obsessed with this song. I feel like it's maybe now not one of the ones that I go back to a lot. I still have an appreciation for it and I think it's really good. But I don't know if this one really grabs me in the way that all of the other songs we've spoken about thus far have. But I yeah I do think that the highlight of the song is that innocence that you're describing and that's just sort of like optimistic energy that you feel when you listen to it and and it's romantic in a really sweet way and like I mean for as you know evil as she can be sometimes like That innocence and that romanticism is also a side of her that exists, and she doesn't always express it or share it, but it's there.

36:23 And it shows up on songs like this. Yeah, I agree. And then number five, I'll remember. This is 1994. Song was number two on the charts, prevented by All For One, I Swear, which is... So I get a kick out of that one. I'm pretty sure she was very happy to know that her song got blocked by All For One Of All People. But this was part of the With Honor's soundtrack. A very underappreciated ballad. She has never performed it live. music video is very iconic very futuristic um it also came off the heels of the controversial sex book and the erotica album so she I think her record label and I think she knew that she needed to tone it down and work with the adult contemporary audience that felt betrayed um by her and I think that she was trying to like you know do some public um repair public uh PR A pure damage control with it.

37:26 It's a very toned down, wholesome, and sentimental song. And it's only on the Something to Remember ballads album. It's not on any other Greatest Hits album. So this song has really been swept aside for years. And it reached number two back then. And yeah, I think it's one of those songs that has really been discarded. Yeah, it really has been discarded. It almost doesn't feel like a Madonna song, even though it is. But I would also say that it's maybe her most like adult contemporary. But this is one of my ultimate favorites. I adore this song.

38:09 I remember when I was in elementary school in the sixth grade it was our elementary school graduation and our teachers had selected us to sing Celine Dion and R Kelly's duet I'm Your Angel as like our graduation song and I was infuriated And I mean, I was literally just 12 years old, but I was so pissed off that they had chosen that Celine song that I actually like I started a movement to have it changed. And I was successful and I got them to change it. I'll Remember So I'll Remember was our elementary school graduation song and I sang it at the graduation ceremony with my graduating class as like my choir so like I'll always have that little story attached to that song for me but I just truly I love this song and you know and it is criminal it is she was not nominated for best Oscar best song because this I mean we have seen things be nominated and win that are so undeserving this song is incredible and I don't know I guess it's a song that she doesn't really think about or really care about that much but ironically Not only did it reach number two, it was one of her biggest hits.

39:32 So there's this amazing Instagram account called Hot Sheets. I don't know if you've ever seen them. So they do a lot of really great chart statistics using the Billboard charts. And they have this like point system in place so that it sort of like creates like a sort of like equal playing field for songs that have like come out, you know, now versus songs that came out like 20 years ago. And they put together and they do all these amazing visuals on their Instagram account. So like if you're a chart nerd like I am, even though the charts mean absolutely nothing now but there was a time where they did kind of mean something and anyway He has a great list of Madonna's biggest hits based on a combination of radio play, chart position, weeks on the chart, sales.

40:21 This song is actually one of her statistically biggest hits ever in the United States. So it wasn't just number two. It was surprisingly massive. It was a big airplay hit. So and even as a kid like I loved this song before I even knew that it was Madonna because I only really became a Madonna fan when Evita came out when I was like nine years old nine ten years old so you know I remember hearing this song on the radio and again it's one of my big favorites I don't know if she'll ever dust it off but this will I mean I don't want to be morbid but I feel like this or live to tell is gonna be the one that like gets played a lot when she passes Yeah, I think I could see the remembrances coming in.

41:08 That will not happen before a long time. Yeah, let's kind of push that far, far away. But someone's going to cover I'll remember and do like an Elton John candle in the wind moment. Yeah cause you know or like yeah cause no one has covered Live to Tell or I'll Remember and I'm like wow you know cause people don't really cover Madonna songs like almost ever you know but speaking of Angel Darren Hayes from Savage Garden did a really good cover of Angel oh yes that is right I haven't heard that in a while but yes you are right about that and also I'm like where were you back then like when you were trying to get when we needed I'll Remember to be number one and kick Offer One off the charts you know like get the radio station but that's also her fault because she didn't do any performances of it she didn't really promote it and it's a testament to what a great song it is because it achieved that incredible chart success just off of it being so good like she didn't promote it so like It's incredible that it was such a big hit with no promotion.

42:12 So next one would be Cherish from the Like A Prayer album. Now, like for the hardcore fans, even maybe casual fans, they would know this song, but like this is a song that has been forgotten over the years. I mean, back when it first came out, like you couldn't, you know, not hear it for a while. And this was the third single after Like A Prayer and Express Yourself. And you know it's like when I think of Cherish it felt like this song really belonged to True Blue because True Blue was in that same vibe you know she was in this very happy place with Sean Penn and you know the Like A Prayer album was kind of like the divorce album it was a very serious album and Cherish seemed to be like this like a bigger contrast to all the other songs on there and so It felt out of place, but it's such a magical song.

43:03 The late Erbritz directed that video. Erbritz is a famous photographer. Very iconic. I mean, the video is black and white. He's on the beach. You know, there's like mermaids. It's incredibly joyous. You know, I mean, who could ever forget the lyric of Romeo and Juliet never felt this way, I bet. Which is like a Beach Boys kind of a verse. And song hit number two. She never had performed it live after the Vondant Mission tour and she has stated that she never really liked that song and I can see why because she's not into the I think she gets very embarrassed when she has to sing songs like Into the Groove or Lucky Star or Cherish because it feels like it's so beneath her but Cherish is such a great song and I think that people really sleep on it Yeah, I think it has a lot in common with the things that you were saying about Angel, about that sort of innocence, that energy, that romanticism, that positivity.

44:05 Like this is a song to listen on like a bright sunny day as you're skipping along the sidewalk. Like this song will make you feel good. This song will lift you up. And I think like between Cherish and Angel, like I would go with Cherish. I really love Cherish a lot too and for me it's really all about the music video like the music video captures that joy and she just looks so beautiful but like in the most like effortless and just sort of pure way like I don't know she's just radiating in that music video like it's not even just about like the beauty of her face it's just like the beauty of her soul coming out in that music video In a way also liberating too because she got out of a very stormy relationship with Sean and you know I know that it's been said that that was like the love of her life but also I think that she felt in some ways liberated from that relationship so I think in some ways that song also made sense yeah um even though it felt like it was like a love song to Sean at that time but you know maybe it's still maybe it was because even though things I don't know but if she wrote it during the like a prayer sessions like maybe she was just like reliving what she felt when they first met you know and sort of just making peace with that

45:38 Yeah, so ready for the next one, Who's That Girl? Now, it's another number one hit song, and it was also for the movie Who's That Girl, which originally was titled Slammer, but Madonna insisted that the title should be Who's That Girl, because I think she was really in love with that title, and Smart Move, because it was... A tagline that would you know follow her over the years and also Song was very successful the tour itself was a massive success and it also kind of like continued on with her her Latin infatuation I mean she before that had La Isla Bonita and so Who's That Girl is like the sister, like the sibling of that song, too.

46:25 So it's like another extended version of La Lista Bonita, but just another, again, a beautifully well done song. Another song that you can cherish, like Angel, like you can go around and just skip around, be at the beach, you know, and start singing the chorus, even if you don't know Spanish very well. Yeah, totally. I mean, I do really enjoy this song. I don't know if it's one of my big favorites, but I really do enjoy it a lot. I enjoyed the four songs from that soundtrack. And it's interesting because... It's like the three main songs from that soundtrack are all sister tracks. It's like, like you said, like, Who's That Girl is basically the sister track of La Isla Bonita.

47:06 Causing a commotion is the sister track of Into the Groove. The Look of Love is the sister track to Live to Tell. So like, in a way, like, you know, the music done for Who's That Girl, like, doesn't feel necessarily like as inspired. It feels like a little bit more repetitive of what she had done on the True Blue album. but it's still super enjoyable but it is a bit strange that like a song that reached number one and like you said you know was the name of the movie was the name of this giant tour like and she left it off of the Immaculate Collection like so and I think that the Immaculate Collection is sort of like I mean obviously brilliant compilation album one of the most important and successful greatest hits album but it's like it almost became like a time capsule in the sense that like all the songs that she chose to put on there have remained classics for the most part but like the big hits that she left off like Who's That Girl like Angel like Dress You Up like they all got forgotten But I think if they had been on the Immaculate Collection, they might not have been forgotten in that way.

48:18 Yeah, and you got a really good point there. And I think that kind of speaks to also the fact that there are songs that she tends to not perform that have been big hits. But she sang Who's That Girl on the first leg of the Rebel Heart Tour. yes she did I was there for that one yeah luckily she did it at the show that I went to and it was a highlight it was amazing especially because she did it like kind of acoustic style yes so and I feel like doing it acoustic style made it like maybe like a little bit less sort of childish in a way because the song has a very young energy like kids would love this song you know oh absolutely and I think that she um I mean I think there's something so exciting when you have diehard fans when they start hearing the first note and like oh my gosh that's who's that girl like this is a song that I haven't heard in a long time it was so exciting especially because I actually went so I went to the Montreal show of the Rebel Heart Tour and that was the opening night of the tour oh wow so no one knew what she was gonna sing so like when she started doing who's that girl we were floored like we couldn't believe it yeah so let's go to number two so Burning Up this came from the first album and it was one of the early songs that she solely wrote she was like the sole songwriter of that song and this was obviously early in her career and this was sent in as a demo she recorded it with her boyfriend DJ Mark Kamens at the time and this song kind of like really goes back to her her punk rock um

49:52 Gritty rock days like she was like with the breakfast club she was playing the drums and the guitar and so she was kind of going more with the blonde kind of like what Blondie the pretenders kind of going that route and burning up is such a Powerful song, the guitar riff and the 80s sound to it and the declaration, the power of her lyrics in that song. It was so respected to the point where Iggy Pop would cover that at her Hall of Fame. And I've seen her perform it a few times. I saw her perform it at the Reinvention Tour.

50:35 She would bring it back for... Rebel Heart and then she brought it back again for celebration. So I think this is a song that I think she secretly enjoys. I think she loves this song. I think the song makes her feel like a badass. It is. And I love it when she brings her guitar out, you know, and just really gets in command. And I'm here for it. I mean, the video You know, it's like, I think she nearly died on that video because the crane fell off. Oh, fun fact about the video. I don't know if you know this. I only recently found out about this. The director of the Burning Up music video directed the first Teenage Mutant Ninja Turtles movie in 1990. Oh, get out of here. Yeah.

51:15 I love that movie. So that movie had a chokehold on me as a kid. Yeah. Well, it also directed the Burning Up video. Wow. Well, there's a reason why I love that song. Yeah. Yeah, but this is a song that didn't chart, didn't make any top 100, which is a failure of her record company because that song is such a classic, but it is an enduring hit for her hardcore fans, her hardcore fans. I decided to put...

52:02 This Used To Be My Playground Another Ballad This Came From A League Of Their Own soundtrack which she performed beautifully in that I love that movie so much especially that dance scene but like I think of that song and at that time I don't think I was a big fan of it growing up because I just felt it was way too melancholy for my taste but I think as I've gotten older and I've had to experience losses around my circle. That song comes to mind because I'm in this nostalgic place. I would go to a shopping mall and be like, oh wow, this used to be where Sears was.

52:43 This used to be where Carson Peary Scott was. So I get into this nostalgia every time I hear the song and it was her number one song and she had never performed it live until she broke out of it at the Celebration Tour when she was in Chicago for the second night. I was there for the first night. Oh no, you missed it by one night. I was angry. I was so angry. The reason why she chose that song is because that's where League of Their Own was filmed. Exactly. I was very angry because I really wanted to hear her play that song and I felt like she missed the opportunity to play it during the MDNA Tour when she did the Like a Virgin, the as a ballad I felt like that should have been replaced by This Used To Be My Playground my opinion but I feel like that would have worked that would have worked that could be interesting for sure this is also a song that is like it's insane that this was not nominated for best song at the Oscars I guess like the Academy just really didn't like her you know because when it's something that I think about literally every Oscar season is that like Madonna has done some incredible soundtrack work It's like we talked and we have three of them on this list.

54:01 Live to Tell, I'll Remember, This Used to Be My Playground, then there's also Crazy For You, there's Beautiful Stranger. Where's the Grammys for that? Where's the Grammys for that one too? But I think the Oscar, like all five of those songs should have been nominated and at least one of them should have won. Like I think she's among the pop artists who has done like the best soundtrack work. She has. I mean, you know, you look at Dick Tracy, you look at... Yeah. You look at Evita, you know, you look at... um what was that god I'm trying to remember they had sung Masterpiece you know that was it wouldn't go in glow but unfortunately the timing the way she I mean I don't think Masterpiece is on the same level as like these five songs but still like come on it doesn't make sense Billie Eilish has two Oscars for songs and like Madonna doesn't even have a nomination like it's criminal that this song especially because League of Their Own was such a big movie it was such a success it was critically well received um yeah and I love the video for this song like when she's going through the photo album and it sort of like you know has these video images in the photo album and she just looks so gorgeous yeah and it just kind of makes me angry that she doesn't get Grammys for these songs because I'm like no yeah I mean I know Mariah Carey complained about not getting Grammys but at least she got nominated and Donna didn't even get nominated which makes no sense Janet barely gets any nominations like imagine Like a Prayer the album not getting a single Grammy nomination like yeah like how does that make

55:32 any sense True Blue I'm like where's that all of it the entire catalog honestly it doesn't make sense yeah I'm perplexed I mean so that kind of like wraps up on the top 10 so yeah I mean quick special mention I'm gonna make this like a quick lightning round get a reaction something to remember Dick Tracy produced by Stephen Sondheim the late Stephen Sondheim and one of my favorite ballads just incredible Swim Ray of Light this was done when Gianni Versace was murdered and you know she recorded that song and came from the Ray of Light album just a genuinely I love that song yeah great song impressive instant you know which came from the music album I mean it was way ahead of its time it's club techno industrial I mean it's crazy I think this is the craziest song in her catalog and I love it Drown World It's a hardcore fan classic, I mean.

56:35 Oh no, this is truly, that's in my top five of all time, for sure. Beautifully written and very much autobiographical in a way to kind of set off the Ray of Light album. Paradise now for me, I would say that I love that song, Perform Live at Confessions. It's the best, that's the best, it's incredible. Beautiful Easy Ride from American Life. Another great song. Should have performed that Madame Max. Teased that one and she didn't perform it. Kind of like annoyed by that still. I think it's Bella Child, but I think it's the title of Child Bella from Madame Max. I really like the song a lot. I mean, I didn't care for Madame Max as an album, but that was a good throwaway hit that she threw in there.

57:18 And I'm like, yeah, perfect. That kind of made it better. Beautiful Killer. from the MD&A album. That she should have performed for an MD&A tour instead of that damn revolver song. Yes, I could not agree more. Could have done it. Rain from Erotica. Rain video. Rain was a really big hit in Canada. So like I used to hear it a lot when I was a kid. I don't feel like it was as big in other territories. And I do feel like it is generally forgotten. The sex book kind of ruined it at that time. I think Rain... I mean if you ask me today I would maybe say Rain is my number one favorite Madonna song on the video I just love it and I remember on the celebration tour Like she was in Toronto before Montreal and Toronto is where she dropped Rain and put in Frozen for the first time because then she would go on to alternate it in different cities and even do take a bow and I was panicking because Rain is my favorite and I was so worried and then when we got to that part in the show and she did Rain I just started crying I was like thank god Wow.

58:28 I wanted Rain so badly. I just wish she did the spoken word part of that song. Yeah. It was still great though. It was like, that was my favorite part of the celebration tour. Yeah. And then Crave, the Tracy Young dance remix. I love that remix so much. It kind of reminds me of Holiday in that version. Yeah. It does because I think that works because like the regular version doesn't do it for me. I think it's very, yeah. Okay. yeah sometimes the remixes are better you know yeah so with that said um yeah any closing thoughts and what do you hope to see from Madonna but this I'm like what are you hoping for because I know the expectation is kind of like pretty low at the moment like I'm very I'm very guarded I'm actually excited for the first time in a really long time however I'm also like very guarded because I'm like I like what I'm hearing so far it's like it it's not like she's trying to hit Like you know hitch on the wagons of hip hop stars and it's like okay like like I don't think it works in her lane like I don't like I love hip hop music but I just don't think it works in this lane for her yeah I mean I'm not even I'm not necessarily thrilled that she's like duetting with Sabrina because I don't feel like I don't feel like that's really coming from a place of like her thinking Sabrina is a great artist and wanting to work with her like I think it's I think that is sort of hitching to the band kind of like when she did the duet with Britney which was awful It is giving me that to be honest but I know that the whole album is not going to be like that you know so like I'm still definitely excited for

1:00:01 the album I think it's going to be at the minimum really good if not great you know Stuart Price and Stuart did such an amazing job with the musical direction on the Celebration Tour so you know and Stuart is an amazing producer so that definitely gives me hope and But this is the thing though like I don't well I mean it's a whole other conversation so I don't want to go too far into it but like you know I think that Madonna is also a really ego based person and so like regardless of how brilliant she is and how much she has accomplished she still has this desperate need to be the center of the universe that she just cannot seem to shake And I think that's why we're getting the Sabrina duet.

1:00:50 But the irony to me is just that nothing sort of makes you look more irrelevant than chasing a trend. And I think Madonna's key to relevancy at this stage in her life, if it's still something that she wants, because she doesn't need that, you know? But to me, the key is just like, you have to make music that is undeniably good and interesting that's the key to relevancy just make good music because you know when you look at Madonna's career from 1983 to 2005 which to me is like no other artist has had a run like that but she would never have been the star that she was at that time had the work not been good and that's the thing despite all the controversies despite her like obsession with fame there was still the art and the art was there and I feel like that's the problem with like the last 15 years is that it's just been more of the fame thing than the actual art so ultimately my hope is just that like can we Just get back to the art And I think we are It's looking very promising It is And I'm hoping that this is going to be a great summer And I'm looking forward to seeing what comes out of it And also I'm pretty sure Because you've had a lot of controversial Madonna takes So I'm pretty sure you've had a lot of Because I know that Madonna fans have been very passionate I know that they do

1:02:21 get with you sometimes Oh they're crazy They are Because I know that when I did our last episode They're like well you guys have always been haters of Madonna and I'm like wow you really what are you talking about like it's just so funny when they like claim like one person which is I actually will take this as a compliment because I'm not that young anymore unfortunately but they think I look young so they were like how they're like you're too young to understand Madonna and I'm like thank you you're right I am too young to understand Madonna which is just so funny because I literally have like I literally have every single Madonna album and single on vinyl I'm obsessed with her music I'm obsessed with her art I've gone to every single one of her concerts like multiple nights like I'm a Madonna scholar I you know what I am and you have to be critical You have to be critical and and it's okay to disagree like and I think that's the like even us having this conversation today like it's so fun like as fans to just get together and talk about the things that we love and the things that we like less like I'm not as big on Angel and burning up as you are but it's still fun to talk about it and to hear your perspective and to know why you like that song or why you don't like that song and that doesn't take anything away from the things that I love or just like if we have like a different opinion It's just crazy to me that people get so worked up and it's like I know And it's like okay if you're that passionate great tell me what you love about it You don't need to like resort to transphobia because I don't like the

1:03:51 same song that you like That's insanity Exactly and I just And the irony is that like Madonna has always been and they are always the first ones to say that like you know to talk about everything she's done for the LGBTQ community and what a fighter she's been for our community and then they turn around and say transphobic things like you guys don't even you claim to be big fans but you don't even understand what Madonna's been trying to teach you Exactly and also like it's not I also think that people really need to get off the all or nothing mentality I just feel like yeah it's like you know I mean we talk about like with you know the Taylor Swift fans and the beehives but I'm also like Madonna fans are no better like I have seen people come after me if I like said well I don't like this song I just said I don't like the song this could be better you know yeah and even if you like and you're even allowed to hate a song you know what I mean it's a song It's like, you're not hating on the person.

1:04:46 You're not diminishing who they are as a person. You're not getting death threats, you know? Exactly. No, I think this fandom, and it's not just Madonna, it's every single fan base. When I post a Mariah video, all the lambs are just as crazy. Trust me. Oh yeah, they are. Oh yeah, they are. They are. The Britney fans are crazy too. And they're all crazy. Like this kind of blind devotion to a pop idol is a kind of mental illness. It's something that we have to like there's something missing there's something going on and but yeah I mean I don't it doesn't affect me personally it's just more like on a sociological level I just find it disturbing but it doesn't like hurt my feelings I'm just like it's just fascinating to me Yeah, and before I let you get going, because I know you're going to get running here, but like, thank you so much for this brief deep dive and anything that you would like to share about for the next, like how the summer is going to look like for you and the projects that you're working on.

1:05:47 Well actually before I say that just very quickly I'm going to give a shout out to one deep cut that is one of my absolute favorites that we didn't talk about Gone from the musical Oh yes That is truly that is in my top five like Rain, Drown, World, Gone those three and Power of Goodbye those three those four are always in my top five and then number five is always variable and for the summer like I'll be performing I'm always performing and I have a new podcast out called The Blank List which I'm doing with two of my friends and basically every episode we give ourselves a category so for example our first episode was most fuckable animated characters and then we have a big debate and we Basically create the top five list of the category that we're talking about.

1:06:35 And it's just really silly and it's really funny. And I think like in these really dark times, like I think this podcast will just give people a little levity and comedy. So yeah. Yeah, that's like the main thing that I have going on right now. Yeah, well, thank you so much. I hope that people get to check out your work at Traynor Wintour on Instagram and just follow the incredible content that you've been creating. Even if you don't agree, just It's okay. It's all right. And it's not rage bait, by the way, because I only say what I believe. I'm not saying things just to provoke. I'm just sharing my opinion because I'm a pop culture commentator, you know?

1:07:17 And it's stupid to be a pop culture commentator and I know how stupid that is, but this is what I love to talk about. Yeah, exactly, you know? But yeah, thank you so much for being on my show and have a great summer. Thank you. You too. Always so fun to talk to you.