Questlove on Controversial ‘SNL’ Music Moments in NBC Doc

As a kid, Ahmir “Questlove” Thompson would go to bed on Saturday nights at 8:30 p.m., but his parents were “cool enough” to wake him up to watch the musical performances on Saturday Night Live as well as Soul Train. So when he got the call from Lorne Michaels to direct a documentary of the musical side of the series celebrating 50 years, he was ready.

But he did more research. “I knew those episodes by heart,” says Questlove, who got the call in 2020 to work on Ladies & Gentlemen … 50 Years of SNL Music and was 4 years old when SNL launched in 1975. “I was trying to do the math in my head. I’m like, ‘Well, it’s 2020 and the anniversary is in 2025. If I can do about five to seven episodes daily, then maybe I can catch up to it.”

Questlove, who won the best documentary feature Oscar in 2022 for Summer of Soul, co-directed 50 Years of SNL Music with Oz Rodriguez and it features interviews with Mick Jagger, Billie Eilish, Paul Simon, Bad Bunny, Miley Cyrus as well as current and former SNL writers and cast, including Conan O’Brien, Maya Rudolph and Bill Hader. The three-hour special will premiere on NBC on Jan. 27.

In an interview, the six-time Grammy winner and Roots bandleader talks about flourishing in his director era, tackling controversial SNL music moments (Sinead O’Connor, Ashlee Simpson) and how making the new doc provided solace since other docs he’s producing — one on Earth, Wind & Fire and another on Sly and the Family Stone — were so emotional it would make him cry.

This doc kicks off with a long, extensive musical mashup of SNL performances — how long did that take to make? 

Eleven months. Here’s the hilarious thing — Lorne approaches me when I’m in the middle of Summer of Soul press, so this is way before the Oscar. I think at the beginning I was like, “I’ll do the 50 best musical performances in SNL history.” That’s where I started. And then I get the hard drive for all the episodes and there’s a 1000-plus. So I prepared for that intro the same way that I prepare for DJ gigs. 

In my opinion, any song has the ability to be deejayed, I just have to sort of categorize it. I have to say, “OK, this song is 82 BPMs, the first part of the song’s in C minor, the bridge is in G and there’s a sustained note that could get me to another.” I break down the science of what the song is. I literally watched a year’s worth of every performance that was on that show, took a note of what keys were what, what BPMs were what and that’s how I prepare for a DJ gig. So for me, that was like my trademark, but it was fun. But I realize now I could have just taken the easy way out and let AI decide.

That’s kind of like the good side of AI in a way, or the productive side.

It could have been, but even then it goes to show you that [humans matter]. I’m not trying to do the microwave versus long cook from-the-oven [analogy], but I do believe that creativity in a human touch is still needed to do certain projects. And I don’t think AI would’ve been that clever. You have to know music.

When you got the call from Lorne to direct this, did he say watching Summer of Soul was one of the reasons he thought of you?

Yeah. The funny thing about the Summer of Soul experience is that people [said], “Wait, did I hear this correctly? You’re directing a movie now?” And I was like, “Yeah.” And there were at least about 40 people in that position that would ask me, and I’d be like, “Why? What’s up?” And they’ll be like, “OK.” It was like they were all waiting by the sidelines to see what happens with Summer of Soul. And then obviously once the green light came up they’re like, “He knows what he’s doing” and then suddenly just a flood, a flood, a flood [of requests]. There’s no feeling like the first time that you become the high school football quarterback champion where you’re the school hero. And that’s what it felt like, where suddenly any project you want to do is at your display.

As I was watching I was wondering if you’d tackle some of the controversial musical moments, like Sinead O’Connor ripping the photo of Pope John during her performance….

I was like, “I want to cover every controversial moment on the show.” Because you got to show the warts and all. If you show the warts and the wrinkles, then that’s what makes it a human story. People haven’t seen her ripping that photo up since it happened on the air; subsequent reruns show the dress rehearsal where it didn’t happen. In light of her passing away, it’s almost like I wish she could see [this]. I befriended her in the early ‘90s when the Roots started touring. That really affected her life in a way. Whereas now with social media, a lot of us are outspoken about what we believe in, controversial takes or not, and she was sort of dragged through the fire, whereas now more or less [outspoken people are] seen as a human. And for Al Franken to say, “You know what? She was right,” to me, that was the important sound bite to show you how history is and how people change and evolve.

The Kanye situation was a little humorous because a lot of our interviewees are like, “I’ll talk about everything except Kanye.” And I was trying to figure out how we could [find] a Kanye angle that doesn’t necessarily speak of just his antics? And it just so happens that Ego Nwodim, her very first show ever was that episode. So that to me is the gift that keeps on giving because she’s one of 40 people standing behind him, and each person has a different story to tell, and it just so happens that her first day is dealing with that. So that to me was the perfect way to kind of introduce Kanye’s effect on the show. And he changed the game. After his performance everybody wanted to do these presentations instead of just perform behind the regular background.

There’s a few that I couldn’t get to cover. I wasn’t able to get to Lana Del Rey’s performance.

I wondered about that one…

Yeah. I went out to a lot of people. I went to Ashlee Simpson and she declined. I think maybe as I get further in my storytelling phase, my fellow peers in the music industry will sort of know that I’m not a gotcha journalist and that I look for the human element in things and the teachable lesson in things, but still able to tell the story. 

Was the first time you performed on SNL in 1999 with Busta Rhymes?

Yeah, it’s weird. So it’s been my lifelong dream to be a music guest on the show. The Roots’ first three years in existence, we lived in London, so we lived in Europe and we weren’t able to be on the show. I’ve been on the show in almost every sort of example except for actual music guests. I’ve backed up two artists on the show. I’ve been a punchline on Weekend Update. I’ve been in a sketch with Timothée Chalamet. I’ve been part of a dialogue. I’ve been in a Lonely Island clip that didn’t make it to air. I’ve been utilized in the show almost in every way except for music guest. So there is a new Roots album coming out this year, so I’m about manifesting my dreams.

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I had wondered if the Roots ever got the offer to perform?

I think at the time, because we were Tonight Show based, it was almost too close for comfort. In any other circumstances, yeah, but there was always a wink to it. But I say dreams are going to come true.

In 2004 you and the Roots backed Toots & the Maytals when Donald Trump hosted. What do you remember about that show?

Oh my God, dog. People ask, “Have you ever been on the show? And who were the musical guests?” And I’m like, “Yo, y’all don’t even know, dog.” Yeah, it’s kind of weird that my episode was Trump’s episode the second time with Toots and Gwen Stefani. The very first time we were on was magic because if someone were to tell me, “You don’t know this, but 10 years from now you’re actually going to be working in this building,” I’ll be like, “Get out of here.”

You’ve been directing a lot more and taking off in the filmmaker space. What’s it been like to embrace that part of your creativity? 

In the beginning it was hard because I think when someone is taken out of their comfort zone and placed in a whole new bubble, the feeling of imposter syndrome always comes to play. So I’ll say the first two years of me being in my new clothes as director [was questioning], “Can I do this?” I always say it’s a journey; every person has a journey of, “Am I?” And you have to reverse it to “I am” and really own it. There’s three other films coming out. There’s a Sly and Family Stone documentary, the SNL documentary, and I’m also working on the Earth, Wind & Fire documentary.

As far as Saturday Night Live is concerned, to me, that was my fun time because the other two documentaries were emotionally heavy, and you’re almost like their therapist and you take on a lot of their pain, a lot of their darkness. There’d be sometimes I’d come home after shooting and start crying, starting to call band meetings [because] you learn things about their band [while] you’re having [your own] band meetings. And so for me, there was a period where I would save my SNL work and research for the weekends like Friday, Saturday and Sunday. This was a labor of love and it was fun for me because sometimes doing those other documentaries were so emotionally heavy for me and draining that I was like, “Man, I can’t wait to watch Season 17 and my favorite episodes.” It’s me having fun.

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Ladies & Gentlemen… 50 Years of SNL Music premieres Jan. 27 at 8 p.m. on NBC and streams the next day on Peacock.