The Questlove Movies Ranked
I of course became aware of Amir “Questlove” Thompson many years ago as the drummer of The Roots. Over the past decade-plus, Questlove has expanded his show business influence and interests with The Roots operating as Jimmy Fallon’s house band and his producing efforts in music, stage, and film. And in the four years since 2021, he has directed three music-based documentary films to augment his wide array of projects. Each of them takes a different tack while ostensibly dealing with similar subjects and they are proving Questlove’s prowess in another medium, albeit one that can certainly be molded as a musical instrument.
#3 — LADIES & GENTLEMEN… 50 YEARS OF SNL MUSIC (2025)
Co-director: Oz Rodriguez
Amid the many festivities for SATURDAY NIGHT LIVE’s (1975-present) 50th anniversary, Questlove and SNL director/producer Oz Rodriguez co-directed LADIES & GENTLEMEN… 50 YEARS OF SNL MUSIC. The TV special documentary runs for just over two hours and is full of great clips from the past five decades and some mostly insightful talking heads. I’ve always had a fascination with the stories behind SNL (although I haven’t watched a full episode in probably over the decade) and this certainly satisfies that itch with narrower focus. “Narrower” is relative to the whole swath of SNL’s legacy. Of course, many, many musical guests and sketches have come and gone from the show. And I’m sure Questlove didn’t feel the scope was narrow as he watched every single SNL episode to research for LADIES & GENTLEMEN. But the awesome extended mash-up cold open establishes the literal rhythm the documentary hits. Certain segments stretch on a bit too long (such as an extended sequence on Kanye’s controversies on the show), but this couldn’t have been done as a comprehensive overview of every interesting music-related thing that’s happened on SNL with even five times the length. Ultimately, LADIES & GENTLEMEN hits the right notes (oof) by addressing the impact of musical acts and sketches on SNL and it’s a breeze of watch augmented by so many great performances.
#2 — SLY LIVES! (AKA THE BURDEN OF BLACK GENIUS) [2025]
Questlove’s second documentary of early 2025 is a profile of Sly Stone. SLY LIVES! (AKA THE BURDEN OF BLACK GENIUS) is perhaps the director’s most “typical” music doc yet. While LADIES & GENTLEMEN certain plays out like a usual behind-the-scenes special, its diverse array of subjects is not like the focus on one figure depicted in SLY LIVES. Questlove’s latest film at the time of this writing both benefits and weakens from the closer look, even though Stone and his work certainly deserve it. I actually teared up at a couple points, especially as the discussion about Sly and the Family Stone’s incredible run of albums in the late ’60s and early ’70s develops. And the more reined in amount of talking heads creates a greater rapport with each of those interviewees. But there is a bit too much repetition to the narrative beats and conventionality to the structure and melodramatic fade-out edit moments, even as SLY LIVES is an essentially moving profile.
#1 — SUMMER OF SOUL (…OR, WHEN THE TELEVISION COULD NOT BE TELEVISED) [2021]
Questlove’s directorial debut set a high bar for himself. SUMMER OF SOUL (…OR, WHEN THE TELEVISION COULD NOT BE TELEVISED), which won Best Documentary Feature at the Oscars (unfortunately) right after “The Slap,” is a fittingly soul-stirring excavation of (mostly) unreleased footage of the Harlem Cultural Festival in 1969. The number of all-time great acts on the bill is astounding and Questlove brings incredible highlights out into extended view. SUMMER OF SOUL does revolve on talking head segments and narration, but the musician-director wisely makes space for some of the more exceptional performances in their purity. I cried watching B.B. King! The sadness of the relative obscurity of the event, which happened the same summer as the mostly white-driven Woodstock, is hammered home by eloquent context-setting interviews, but most importantly, by the vitality of the footage and the performers and audiences it depicts. I feel the moment in time so viscerally watching SUMMER OF SOUL and it remains Questlove’s best cinematic ode to music and Blackness.
