2000S Episodes

De La Soul’s Maseo sits down with Questlove for an unfiltered deep dive into his Hip-Hop journey, his approach to deejaying, and the making of a true original. From volatile days in Brooklyn and Long Island to early block parties and the creation of classics like “Me Myself and I,” “Afro Connections,” and the epic “Cool Breeze on the Rocks” splice session, Mase breaks down the art, risk, and innovation behind De La’s catalog. He explains how a skipping record sparked a 20-minute freestyle, how a...

Questlove sits down with R&B icon Eric Benét for a deeply human, wildly musical conversation tracing the singer’s journey from Milwaukee family harmonies to gold plaques and Grammy nominations. Benét opens up about early sonic imprints like Burt Bacharach, Dionne Warwick, and “Wichita Lineman,” his Alabama and Mobile roots, and how discovering Questlove’s own lineage story reshaped the way he thinks about ancestry, Haiti, and spirituality. The two dig into Prince vs. Michael Jackson, a legendary James Brown clip, and what it really meant to grow up in Milwaukee during the Jeffrey Dahmer years. Benét breaks down his path from band life to major labels, the making and shelving of Better and Better, how David Foster and Dean Parks helped shape Hurricane, and why songs like “Spend My Life With You” and “Sometimes I Cry” never get old on stage. Along the way, the longtime friends talk vocal maintenance, the emotional cost of fame, the rise of Neo-Soul, and what Benét would tell his 1…

During the recent Thundercat episode of The Questlove Show, the creation of MF DOOM's iconic mask was misattributed. After QLS past guests (shout out to Dante Ross), friends of the show, and our legions of dedicated listeners called out the mistake, The Questlove Show is proud to set the record straight by welcoming the mask's original and sole creator, KEO—a longtime friend, collaborator, and creative partner of DOOM. In this QLS mini, KEO tells the story in his own words, sharing the true o...

Drummer Cindy Blackman Santana joins Questlove Supreme for a career retrospective. She recalls her Ohio childhood, moving to Connecticut, and early days in New York City. Cindy details learning under Jazz legends Tony Williams and Art Blakey and how she was part of an essential movement in the genre during the 1980s. After working with a who's who of Jazz and cementing her own legacy, Cindy details the conversation and audition that would make her a keystone figure within Lenny Kravitz's band. She also describes staying ageless while balancing music and marriage with past QLS guest Carlos Santana.

Amerie sat down twice with Questlove Supreme for this extended episode. The conversation examines the singer's upbringing and passion for reading and information. The self-proclaimed "military brat" explains how her years in Washington D.C. informed her musical taste and why she created albums with a different sound than many of her R&B contemporaries. Amerie also speaks about her breakthrough songs, label woes, and why she does not believe in charging for features. This episode is for QLS listeners who enjoy our trademark rabbit holes—with twists, turns, and laughs.

This episode of QLS is a special one-on-one between Team Supreme co-host Unpaid Bill and top songwriter and producer Sam Hollander. Sam, who made hits alongside Metro Station, Fitz and the Tantrums, Panic! At The Disco, and Gym Class Heroes, emphasizes his bumpy career journey. This trajectory includes dropping out of college, a record deal at a famed Rap label, and purposeful collaborations with Carole King and The O'Jays. Sam peppers humor and self-deprecation into a story that offers hope for any impassioned creative. Hollander's book, 21-Hit Wonder: Flopping My Way to the Top of the Charts, chronicles this experience. This episode took place at Renaissance Recording with engineering by Isaiah Abolin.

Twenty-five years after "You Got Me," Eve and Questlove have an in-depth conversation alongside Team Supreme. The Grammy-winning, chart-topping Hip-Hop artist is joined by author and historian Kathy Iandoli to discuss her new memoir Who's That Girl? The discussion traces Eve's steps from West Philadelphia to Hollywood to London and success in music, film, and television. Listen as Eve's passion for rapping and her journey with self-love are apparent in this special conversation.

QLS gets in the weeds with Mr. Walt and Evil Dee of Da Beatminerz. This free-flowing discussion traces the origins of a very gritty sound and frequency of 1990s Rap production. The two brothers are not above clowing one another as they recall working on Black Moon's classic debut Enta Da Stage, going crate-digging with Q-Tip, and helping to make D&D Studios a true enclave of hardcre Hip Hop. True to Da Beatminerz' name and sound, this episode digs deep.