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Questlove: Great Cameos And Acting Roles By The Oscar-Winning Musician And Filmmaker

Questlove accepting his Oscar
(Image credit: AMPAS)

There are actually many musicians who have delved into the art of filmmaking (such as Rob Zombie, who has directed many notable horror movies, and Madonna, who is currently working on her own biopic). However, a rare few of these multi-talented artists have gotten attention from the Academy, including Questlove - whose Hulu original, feature-length directorial debut, Summer of Soul (…Or, When the Revolution Could Not Be Televised) won the Oscar for Best Documentary at the 94th Annual Academy Awards.

Born Ahmir Khalib Thompson, Questlove is best known as the drummer for the hip-hop group The Roots, which was founded more than 20 years before they became Jimmy Fallon’s house band. The permanent TV gig - which has seen him and his bandmates participate in many fun sketches, including the popular Classroom Instruments segment - would also open doors for the musician to make appearances in other movies and TV shows, often as himself. However, we will begin the following list of some of our favorite Questlove cameos so far with one of the first times he played an original character.

Questlove as Curly in Soul

(Image credit: Disney)

Soul (2020)

Questlove’s Summer of Soul - one of many great documentaries about Black culture in music - is not the first Academy Award-winning film that he has been involved in (nor is it his first film with the word “soul” in the title). In 2020, he leant his voice to the cast of Pixar’s Soul in the very fitting role of Curly, the drummer for a jazz quartet that Jamie Foxx’s Joe Gardner joins right before his untimely death, setting him on an adventure across the afterlife in an attempt to return to Earth. Questlove also served as a music consultant for the acclaimed Disney+ exclusive (despite a successful theatrical run overseas), which won Oscars for Best Original Score and Best Animated Feature in 2021.

Questlove and The Roots on iCarly

(Image credit: Nickelodeon)

iCarly - Season 6, Episode 7 (2012)

One of the many awesome celebrity guest appearances on this episode of iCarly’s sixth and final season (before its Paramount+ revival in 2021), called “iShock America,” is Questlove, as well as the rest of the legendary Roots crew. The one-hour special, which originally aired on Nickelodeon in 2012, sees the hosts of the titular web series within the show (Miranda Cosgrove, Jeanette McCurdy, Nathan Kress, and Noah Munck) appear on Late Night with Jimmy Fallon, where an accidental moment of indecent exposure forces the gang to pay a fine worth thousands of dollars.

Questlove and Jim Gaffigan on The Jim Gaffigan Show

(Image credit: TV Land)

The Jim Gaffigan Show - Season 1, Episode 7 (2015)

Questlove is also one of many celebrities who play themselves on an episode of another sitcom - namely The Jim Gaffigan Show - on which the title character is scheduled to appear on Jimmy Fallon’s talk show. The drummer pops in to say hello to Jim Gaffigan (playing a fictionalized version of himself on the short-lived TV Land series he also co-created) backstage at The Tonight Show Starring Jimmy Fallon, where he says he can’t wait to hear more of his “food jokes” and asks him to sign his drumsticks for a charity event. He also meets Jim’s friend, a Zimbabwean priest named Father Nicholas (Tongayi Chrisa), whom - much to Jim’s surprise - Quest invites onstage to play the tambourine with The Roots.

Questlove on Parks And Recreation

(Image credit: NBC)

Parks And Recreation - Season 7, Episode 7 (2015)

The seventh and final season of NBC’s hit dockumentary-style sitcom not called The Office saw the Parks and Recreation cast gathering for the marriage of office manager Donna Meagle (Retta) to Joe (Keegan-Michael Key). At the very end of the episode, during the reception, the bride was treated with the surprise appearance of Questlove as her estranged brother LaVondrius, whom Donna previously said she “hated” without specifying why. Her sibling (sort of) clears up the mystery by bringing up an old argument involving a microwave and showing that he is not over it either by promptly smashing the device on the dance floor.

Questlove in Popstar: Never Stop Never Stopping

(Image credit: Universal)

Popstar: Never Stop Never Stopping (2016)

A film that has one of the greatest assortments of celebrity cameos ever, particularly of people in the music business, is Popstar: Never Stop Never Stopping - a hilarious and criminally underrated mockumentary written by and starring The Lonely Island. Questlove shows up pretty early as one of the famous talking heads showing their appreciation for the Style Boyz (the hip-hop group Andy Samberg’s conner4real was a part of before going solo). He says he admired the trio for their authentic chemistry and friendship, at least until their ugly breakup.

Questlove on Inside Amy Schumer

(Image credit: Comedy Central)

Inside Amy Schumer - Season 4, Episode 4 (2016)

On the night when Questlove accepted his Oscar for Summer of Soul, one of the three women hosting that year’s ceremony was Amy Schumer, whose own Comedy Central show, Inside Amy Amy Schumer, once enlisted the drummer for a funny bit from its fourth season. Quest appears dressed as an 18th-century revolutionary to help Amy pitch an idea for a new “hip-hopera” about Betsy Ross to Broadway superstar Lin-Manuel Miranda. Outside of dropping a beat on his old school snare, Quest remains silent for most of the scene until after the Tony-winning artist leaves, prompting him to reveal that he was only willing to participate in the pitch because Amy promised he would get tickets to Hamilton.

Questlove in Someone Great

(Image credit: Netflix)

Someone Great (2019)

Drumming is not Questlove’s only musical talent, as seen by his cameo in the Netflix original rom-com, Someone Great - one of the best Gina Rodriguez movies - from 2019. The former Jane the Virgin cast member plays an aspiring music journalist recovering from a breakup who embarks on one last night out in New York City with her two best friends (Brittany Snow and DeWanda Wise) before moving to San Francisco for her dream job. A major stop on their farewell tour is a club called Neon Classic, where Quest just happens to be the guest DJ spinning records for the night.

Questlove actually served as the in-house DJ and musical director for the 93rd Academy Awards ceremony, which makes his Oscar win just the following year especially worth celebrating. I wonder if this is just the beginning of what could be a wonderful filmmaking career from the beloved musician. 

Jason Wiese
Jason Wiese

Jason has been writing since he was able to pick up a washable marker, with which he wrote his debut illustrated children's story, later transitioning to a short-lived comic book series and (very) amateur filmmaking before finally settling on pursuing a career in writing about movies in lieu of making them. Look for his name in just about any article related to Batman.