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Questlove charts 50 years of SNL musical hits (and misses)

"Pretty much any Saturday that The Roots aren't touring and they're taping, I'm in the audience watching," Questlove says of SNL.
Eugene Gologursky
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Getty Images North America
"Pretty much any Saturday that The Roots aren't touring and they're taping, I'm in the audience watching," Questlove says of SNL.

By his own account, Grammy-winning musician and The Roots bandleader Ahmir "Questlove" Thompson has been involved with Saturday Night Live in every possible role — except for the one that he wants most.

"I've been a punchline on 'Weekend Update.' I've been part of a Timothée Chalamet sketch. I've been mentioned in monologues," he says. "I'm a part of that ecosystem almost in every way but the one way I want to be, which is musical guest. ... The Roots are working on their 17th album right now, so I'm still hanging on to my dream."

Now, as SNL marks its 50th anniversary, Questlove has a new documentary, highlighting the musical guests and music comedy sketches featured over the decades. Ladies & Gentlemen... 50 Years of SNL Music is the work of a storied musician and filmmaker who remembers watching the show when he was a kid growing up in Philly.

"I was there from the very, very beginning," Questlove says. "[There] was nothing like it. I know that's the cliché that you're going to hear a lot about this 50th anniversary, but there was truly nothing like it on television."

One change he's noticed over the years, both on SNL and on The Tonight Show Starring Jimmy Fallon, where he's bandleader, is that today's musical guests are more likely to be lip-syncing than their predecessors were. He calls it the "post-Thriller effect," whereby musicians feel pressure to dance and perform perfectly every time.

"The Thriller effect is, it must be perfect," he says. "And I'm kind of from the school of warts and all. Like, I love seeing the warts. I love seeing the pimples, the mistakes. To me, that's the human touch. And I think people need to trust that more. But, you know, things don't have to be Instagram filter perfect 24/7."

Part 2 of Fresh Air's interview with Questlove, about his other documentary on Hulu, SLY LIVES! (aka The Burden of Black Genius), will air in coming weeks.


Interview highlights

On the documentary portraying things going wrong or not as planned  

That's the thing about SNL is there's a risk factor involved. And usually it starts with "no." Like Eddie Murphy talks about, I did not want to do hot tub with James Brown. Justin Timberlake goes on and on about trying to convince Beyoncé to do this "Single Ladies" sketch. Like, everything starts [with] "no." And it's, like, "Wow, you almost talked yourself out of history." And I'm trying to get people in the mind state that, oftentimes we get in our own heads about why something won't work. And sometimes you just got to take a risk and you never know. This might be part of the American fiber, the history of it.

On a 2004 incident in which Ashlee Simpson was shown to be lip syncing on SNL

Ashlee Simpson had a sore throat and was a little iffy about her singing, so she opted to lip-sync instead. And her drummer, who's controlling on the music, accidentally plays the wrong song for the second song.

They could have just patiently just stopped the song and started all over again as if nothing happened. But she infamously does a weird dance and runs offstage, kind of humiliated, and they go to commercial. It just so happens that Oz Rodriguez, my co-director of this documentary, said that they also have the audio recording of the production room, like what was happening at the time. And for me, it was so hilarious to hear the producers and the directors inside of the control room. To me, it sounds like a bunch of teenagers that stole their parents' car in San Francisco and the brakes just give out in a San Francisco hill going down 100 mph. Like, what do we do? Oh no! You get to see what's under the trunk. And that, to me, is the most fascinating part of SNL, how it's able to happen every week without fail.

On SNL introducing America to rap

Saturday Night Live is the first time that America and the world will get to see what hip-hop culture is. The very first rap performance on TV is when Deborah Harry hosts the show in 1981 and brings on Funky 4 + 1. … There were other popular groups at the time, like there was Grandmaster Flash and the Furious Five and The Sugarhill Gang, both [with], like, platinum hits and really music- and culture-changing songs at the time. But she took a liking to this group because it was similar to Blondie, a band that had a woman in the lead of it. …

For me, that's such an SNL move where those first 10 years, they weren't about who's the most popular person to bring ratings? And it was always like the cool factor, like, who's the most popular person now? Who's the person under that person that we could give a boost to? And that's like a prime example of how SNL always had their finger in the pulse of who's next. And as a result, come 20 years later, a lot of those first-time acts … like them getting Run-D.M.C. before Run-D.M.C. was Run-D.M.C or them getting Prince before Prince was Prince, or the Talking Heads or Devo, whoever. A lot of those risks that they took in the first 10 to 15 years, those guys will wind up being, like, the household names and the fiber of the mainstream once SNL becomes the mainstream, instead of the underground. So Deborah Harry using her power to bring attention to a culture that no one knew about like that is a prime moment of the SNL effect and how it builds American entertainment culture.

On the un-hummable SNL theme song

It's the most iconic, nondescript theme song. Pretty much any Saturday that The Roots aren't touring and they're taping, I'm in the audience, watching, and that, to me, is one of the most humorous things ever. Like, you know it when you hear it, you know, that's SNL. It's a feeling. It's almost like it's the last theme that offers a feeling, but not any evidence of it. It's like trying to put water in your pocket or something like that. It's abundant, but it's whatever you want it to be. … I admire the fact that SNL, for 50 years, has been able to provide a feeling without necessarily melodic evidence to it.

On musical guests at The Tonight Show being consumed with nerves

I'm really big on micro meditation and just sitting in a quiet room for, like, 10 minutes before I go on, because sometimes you have to just calm yourself down so that you can really focus on what you have to do. But a lot of times, artists are in their own heads and they often talk themselves out of the magic, because when you're worrying, you're almost praying for something bad to happen — that's my definition of worrying. "I hope I don't mess up." You're basically saying, "Hey, I would like to mess up," just subconsciously. So as a result, most artists will stall, take their time, be an hour late, be two hours late, not show up at all, hijack their career in the name of fear. And as always, once you do it, then it's, like, that's all it was? No big deal. But I'm used to it, because I've been doing this for a couple of decades. Oftentimes, I'll pull an artist to the side and just be, like, "OK, I want you to listen to my voice. I want you to inhale. Exhale." I do that a lot to them, especially the new artists that are nervous and scared.

Ann Marie Baldonado and Anna Bauman produced and edited this interview for broadcast. Bridget Bentz, Molly Seavy-Nesper and Beth Novey adapted it for the web.

Copyright 2025 NPR

Combine an intelligent interviewer with a roster of guests that, according to the Chicago Tribune, would be prized by any talk-show host, and you're bound to get an interesting conversation. Fresh Air interviews, though, are in a category by themselves, distinguished by the unique approach of host and executive producer Terry Gross. "A remarkable blend of empathy and warmth, genuine curiosity and sharp intelligence," says the San Francisco Chronicle.
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