“Every Week Is a High Wire Act”: Questlove and Maya Rudolph on 50 Years of Saturday Night Live

After a half-century of America’s favorite variety show, there’s quite a legacy to revisit. Some of the most iconic moments on Saturday Night Live came from not just its celebrity musical guests, but the crossovers between them and the cast—so says Ahmir Thompson, better known as Questlove, the musician, storyteller, and frontman of Roots, The Tonight Show’s house band. It took him three years to parse through every single episode of Saturday Night Live—one per day—in search of the most tense, beautiful, and meta musical moments on the show, from pre-zeitgeist Beyoncé (“That sketch was the last time she showed up anywhere without any fanfare”) to Bono going rogue (“He might’ve given Amy a kiss on the cheek”). The result is his brand-new documentary. Ladies & Gentlemen … 50 Years of SNL Music, a remarkably intimate and comprehensive chronicle of the show’s rich musical legacy. To celebrate, Questlove called up SNL veteran Maya Rudolph to walk down memory lane, from impersonating Prince—in front of Prince—to going off-script with Queen Latifah.

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QUESTLOVE: So wait, are we just speaking?

MAYA RUDOLPH: We are, but I’m technically supposed to be asking you questions, which is funny.

QUESTLOVE: You know what story unfortunately got put on the cutting room floor that I think would be of interest? Can you talk about—

RUDOLPH: I love that you’re interviewing me already.

QUESTLOVE: So nothing made the cut unless it had risk to it, but one of the stories I had to leave on the cutting room floor was you and Fred [Armisen] trying to psych each other out to approach Prince and doing “Prince Show.” Could you talk about that? Something made you say, “Okay, I’ll try.” And then next thing you know, you step into history. That’s kind of the common fact. Eddie [Murphy] didn’t want to do “Hot Tub.” Jimmy [Fallon] didn’t want to go to Mick Jagger’s room to pitch him anything. When you guys did “Prince Show,” who’s the person that drew the shortest straw to get him?

RUDOLPH: We both went together to his soundcheck, and his assistant, Ruth, was talking us through it. She was like, “Look, he’s going to be done soon.” I think they’d given him the script.

QUESTLOVE: Did he read that script?

RUDOLPH: He didn’t look at that script, but we had gone through the proper channels. The team already had the sketch. Then we went to soundcheck, which we both would’ve been at anyway. It’s not like anyone was pulling my arm to go to a Prince soundcheck.

QUESTLOVE: You were allowed to watch it?

RUDOLPH: Yes.

QUESTLOVE: I would’ve thought that some artists kick people out during soundchecks.

RUDOLPH: I’m sure they do.

QUESTLOVE: I remember I wasn’t allowed to watch a Frank Ocean soundcheck and I was like, “Dude, I just played with you on stage a week ago.” But I understand new artists get nervous.

RUDOLPH: I don’t think people were allowed in for Chappell Roan recently, but I wouldn’t have known because that was the day that Kamala came, and I was dressed as her, and my brain was on fire just waiting for her to land. And the Secret Service were everywhere. Anyway, we go to soundcheck. Ruth is walking us through like, “Okay, he’s going to come off stage, and he knows that you guys are waiting to talk to him about the script.” So we’re standing there, he finishes, he jumps off stage as you can only imagine he would’ve jumped off stage instead of using the stairs. And he walks directly towards us and then instantly makes a 90 degree right turn away from us, and then a left out the stage doors.

QUESTLOVE: Did he give you a pound?

RUDOLPH: Nothing.

QUESTLOVE: What was going through your head? How tall he is, right?

RUDOLPH: Oh, it was more than that. It was a full-body experience. We were standing there looking so thirsty. But then the 90 degree turn made me go, “Oh shit.” So we kept chatting with Ruth, being casual. I’m like, “Maybe he needs to go get some water and he wants to have this conversation in his dressing room—”

QUESTLOVE: Next to the water cooler.

RUDOLPH: Yeah. He’s waiting by the water coolers being super friendly.

QUESTLOVE: Right.

RUDOLPH: At the same time, we’re holding the idea that this artist who we respect and love might be offended by this script, so we’re trying to be friendly and wait. At one point someone checked in about it and they were like, “Oh, he’s gone.” He left the building. Apparently he went straight out those double doors to the elevators and down to his car.

QUESTLOVE: Do you know how hard it is to walk straight to the elevator and instantly get out the building with no lag time?

RUDOLPH: And who knows if that really happened? We want that to be the story because all of our Prince stories are magical. But we have no idea if he ever read that script. And then the choice was, do you do the sketch anyway with the artist watching you do an impression of them? 

QUESTLOVE: What did that feel like?

RUDOLPH: Oh, it was brutal. When you work at SNL, you feel cool because you get to do the cool stuff that not everybody gets to do. And then when you’re the sketch performer and the real musician’s there, you feel like an utter fool—at least I do. But I was also simultaneously trying to project love, which he obviously knew, or else he would’ve canned the sketch. There was another time, I can’t remember if De Niro was the host, but Destiny’s Child was on, and I played [Beyoncé]. And I remember having to walk up to her at goodnights and say, “I’m so embarrassed that I just played you in front of you.” And she was like, “No, it was good.”

QUESTLOVE: Timberlake shared the story of what they had to go through to get Beyoncé to do the “Single Ladies” bit and how it started as a hell no. And I understand the SNL ecosystem, and I also understand that the right 45-second moment can literally change your life. This is kind of a wild take, but I watched that entire Paul Rudd Beyoncé episode, and I have reason to believe that that particular episode was Beyoncé’s tipping point.

RUDOLPH: Why? Because she appeared on the show as herself?

QUESTLOVE: I believe that that sketch was the last time she showed up anywhere without any fanfare. When she’s part of the sketch, and then she comes from backstage and goes to Paul Rudd. Now, I’m certain if she goes to Costco or whatever, it’s going to be Beatles pandemonium, right?

RUDOLPH: Right.

QUESTLOVE: So instantly I knew we’re in a time period in which she hasn’t exactly had her zeitgeist moment, and I feel like the silliness of that moment humanized her because the reception she got when she did “Single Ladies” as her second song was such an enthusiastic applause that was different from when she did “If I Were a Boy” for the first song. It was almost like the audience had a turnaround moment like, “Oh wow, we’re going to invest in this person.” The reception of “Single Ladies” was the beginning of the true arrival, so I almost feel like her tipping point moment happened right after that sketch.

RUDOLPH: That makes sense because something I was always fascinated with working there was when people have to give in to the SNL environment because it’s a live show and there is a bit of a vulnerability to that. It’s an energy thing that can’t be equated with anything else. The audience can physically see the person relinquishing a little bit of their own artistic control and saying, “Okay, I’m going to be part of your fun.” Which is really what the show is. Come play with us, come be a part of our thing.

QUESTLOVE: Well, let me ask—

RUDOLPH: I love that I’ve not asked you one question.

QUESTLOVE: I’m sure they’re not complaining right now.

RUDOLPH: They’re not. It’s perfect.

QUESTLOVE: Lorne [Michaels] offered this to me in early 2021, so I decided I was going to be on a daily diet of three to seven episodes every day.

RUDOLPH: I remember you were like, “Wow, I haven’t watched all these.”

QUESTLOVE: Right. So I went from 1975 straight forward.

RUDOLPH: For how long? Since ’21?

QUESTLOVE: Yeah. I went through every episode. The thing is, around ’87, I saw more magical moments with the cast members providing the music highlights than actual performers.

RUDOLPH: “Cowbell” comes to mind when you say that, right? That’s a musical moment.

QUESTLOVE: First of all, telling a three-hour story about a 50-year history is one of the most impossible things in the world to do. So they let me off the hook, not having to deal with “King Tut” or “Cowbell.” I didn’t mention “King Tut” at all because Steve Martin already covered “King Tut” in his two-part documentary, and “Cowbell” had its own special, so that saved me. But I took notes on what I felt was iconic enough to be discussed, and honest to goodness, I could have done an eight-hour special just on the evolution of music in SNL. Whittling that down to just one episode was one of the hardest things ever.

RUDOLPH: As a fan of the show before I was on the show, I noticed when there was crossover between cast and musical guest. I was talking to Dana Carvey recently about when he got to play drums via satellite with U2 as Garth, and that was because at that moment in pop culture, everything was united. It’s like when Aerosmith did the Run DMC video. You were like, “Oh, everybody’s friends. That makes me feel good.” And as SNL and the cast became cool in the audience’s eyes, the musical guests were coming in also as fans.That definitely happened in the ’70s, no question. With the original cast, they were all friends, they were all intermingling, but the cast that I grew up watching, I noticed that magical sparkle of, “They’re fans of each other, and they want to do each other’s stuff.” Of course, then you start to see the musicians show up in the sketches and they’re in on the joke, which just makes them cooler and more personable. 

QUESTLOVE: Well, if you’re inside the system, is there any space for you to discover new things? Once I came to The Tonight Show, there was part of me that was feeling obligated to know certain things. I was grappling with the idea of these Brooklyn indie bands. I got to learn who Animal Collective and Vampire Weekend is.

RUDOLPH: Dirty Projectors.

QUESTLOVE: Yeah, Dirty Projectors. I now have to study them for my occupation. And I wasn’t getting music in the natural way that I used to get it. Now it’s like my job. When you’re in the Saturday Night Live tornado, do you even have time to learn of new acts, or is it brought to you like, “Do Beyoncé Knowles,” and you’re like, “All right, give me a tape and I’ll study her”? I’m certain that you never said, “One day, I’m going to do a good Whitney Houston.”

RUDOLPH: No. My best friend, Emily Spivey, was like, “I know you, and I know you’re going to do a good Whitney Houston.” So she just wrote it. There’s the element where the writers say, “I’m going to have you do Oprah.” And I’m like, “I’ve never done Oprah. I’m going to need a VHS tape to study.” Which is exactly what happened.

QUESTLOVE: Even Oprah requires musicality because all your intonations have to—

RUDOLPH: That’s exactly right. I went to Darryl Hammond and I said, “I don’t know how to do this.” And he’s the one that talked to me about the intonations. I was scared shitless because I grew up watching her, but I never expected to play her. 

QUESTLOVE: You mentioned in the doc that there’s a point where SNL just takes over the pop culture conversation. I’m part of the generation that got their notes on what Frank Sinatra, James Brown, and Stevie Wonder were like, not because I was familiar with those three, but because of Eddie Murphy imitating them.

RUDOLPH: Right. 

QUESTLOVE: And I realized that everyone’s imitation of Oprah is secretly your imitation of Oprah and your intonation. And then suddenly we “da-da.”

RUDOLPH: Yeah, my son was watching a video game the other day. I don’t know if it was Fortnite or something else. And I heard, “Da-da-da-da.” I said, “That pop culture seed was born from your mother.” Which was really born from us fanning out over Oprah’s Favorite Things.

QUESTLOVE: Have you ever witnessed a musical rogue moment on the show? 

RUDOLPH: I mean, Ashley Simpson is the biggest one.

QUESTLOVE: Were you in the cast during that?

RUDOLPH: Oh, yeah.

QUESTLOVE: She’s one of the people that declined to be interviewed. And I understand, especially with people not being familiar with my storytelling style, not wanting to relive a dark period. I would’ve taken a whole other angle in telling that story, and we were going to drop it because we didn’t have anything, but at the last minute we realized that we had the audio tape of the producers’ room as the show’s going on.

RUDOLPH: From the control room? Oh my god.

QUESTLOVE: It’s almost like when we watch the Hindenburg and our only soundbite is the guy giving commentary on the ground like, “Oh no, what’s happening?” But to hear the black box tape of the control room, the only way I can describe it is like four teenagers who stole their parents’ car in San Francisco, and the brakes gave out, and they realized they’re about to go a hundred miles per hour down a hill and don’t know what to do. The way they’re screaming at each other is revelatory to me. I love to know how people handle things when Plan A doesn’t work, so we just showed the clip with the control room audio on top of it.

RUDOLPH: Well, that’s actually a more interesting way to tell the story because the truth is, it’s a high wire act every single time it’s on. Every week is a high wire act, so you have that inherent trust that it’s going to go okay, but sometimes things don’t. That’s reminding me now, me and Amy [Poehler] were in a sketch with Queen Latifah, and we are singing medleys, and I remember hearing, “We have no playback,” so we sang with no music. 

QUESTLOVE: When you’re put in that situation, I guess it’s like an ’80s Lakers era where you just have to internally know that Magic Johnson’s going to pass the ball to you without looking. So with all this talk of the 50, for you, what were the best performances that you got to witness in that room? You were there in an era where there was so much magic. Was there a particular one?

RUDOLPH: I was like, should I ask you that? I’m assuming you’ve been in the room a ton, especially because you work so damn close. I was there for years, but you get to walk upstairs and watch stuff if you want to. 

QUESTLOVE: I insist on watching. I don’t like watching stuff in the green room because there’s always other people in the green room, and then there’s some people that are there to network and make a connection.

RUDOLPH: I can’t even imagine. That just gave me a hot flash. [Laughs] I think one of the first shows that I did, Neil Young did “Silver and Gold” and I remember feeling like, “This is the most magical room I’ve ever been in my life. I can’t believe I work here.” 

QUESTLOVE: Oh, I saw one where you lost your mind. U2 was the musical guest, and they decided at the 11th hour to just keep playing after the credits. They played an additional 25 minutes. You guys were collectively losing your mind on the side of the stage. “Wow, this is really happening.” Bono was doing prime Bono. I think at one point he rode that long camera thing.

RUDOLPH: He might’ve given Amy a kiss on the cheek, I can’t remember. It’s like rock and roll high school. That’s what it feels like when you’re in the cast and cool people want to be there. Same thing happened with Arcade Fire. 

QUESTLOVE: I was there. Wait, you were on the cast then?

RUDOLPH: Yeah. I had come back from maternity leave. 

QUESTLOVE: I believe at the time we were working with Elvis Costello on his album, and he would do his vocals in our dressing room. It was his version of going rogue and making a demo. I didn’t want to be there while he was cutting his vocals, but my engineer Steve hits me up around 12:45 a.m. like, “Come by and listen to some of these Costello roughs.” And I get there, and The Tonight Show is on the sixth floor, and all you hear is thump, thump, thump. I was like, “Is there a herd of elephants on the seventh floor?” And Steve’s like, “That’s not the seventh floor, that’s the eighth floor.” Two floors up, and I could hear this building shake. So I ran up to the eighth floor at 1:05 a.m. like, “Wait, why is Arcade Fire still performing?” I remember that’s the first time I met Scarlett Johansson. Man, I got so familiar with who Arcade Fire was. That was a magical moment where I didn’t realize that I was witnessing.

RUDOLPH: The first time White Stripes came on, we all went out to watch, and I thought, “This is probably the closest I’ll ever feel to one of those girls that’s about to faint watching The Beatles.”

QUESTLOVE: You know what? He mentioned that he knew he made an impression on you. He mentioned that two minutes before coming on, he just felt like that was the first time he walked into his not-Detroit indie band moment, and he looked at your face, and it was something about your face that gave him energy to seize the moment. 

RUDOLPH: Really? I’m dead.

QUESTLOVE: It’s only happened twice. There’s a moment where Paul Simon and Edie Brickell first lay eyes on each other. She’s doing “What I Am,” and suddenly she just gets frozen. Even though she’s singing, you can tell she’s focused on one thing. Paul Simon later explained that he had heard so much about the singer and liked that song, so he just happened to be standing. Is there a music moment that you regret not witnessing? 

RUDOLPH: Oh, yeah. You don’t get to go out to floor all the time. In fact, a lot of those early days I was pumping milk in my dressing room, and in that era I was missing out on a lot. I was the only one with a baby at home. But I have one question. It’s about the intro. I don’t think anyone’s going to read this and not have questions about that intro. It took you 11 months. In 2021, when Lorne asked you to do this, did you already know?

QUESTLOVE: Initially I was just like, “Okay, deal.” I was busy campaigning for the Oscar I didn’t know I was going to win yet. And when I made the commitment to watch every episode in its totality, I got to 1987 and noticed there were more non-music guest performances than actual music. I had to go back to the beginning and watch everything all over again, and I kept these meticulous notes. I treated it like it was a DJ gig. When I do a DJ gig, I think, “What 20 songs are going to go with this one particular song?” So me and my assistant, Geraldine, went through all these songs in all these periods, and when I finally brought our editor John McDonald all my notes, imagine Doc Brown in Back to the Future carrying all those tubes. McDonald says to me, “Wait, you watched every last episode?” And I was like, “Yeah, these are the songs that are in 88 BPM. These are in 100 BPM. These are the songs in D Minor in which the bridge goes to F.” And he chuckles to himself like, “I kind of took the liberty to do the same thing, but I just threw all 1400 episodes inside the generator.” And I said, “Wait, so all I had to do was just feed all this stuff inside of an AI thing, and it tells you what key it is and all that?” 

RUDOLPH: Oh my god.

QUESTLOVE: But I realized that words can be connections too. The fact that Sharon and Hanson can have something in common with Run DMC and Jimmy Jam and Terry Lewis is like building this mile-long Babylonian Tower of Jenga, and then NBC lawyers come to you and say, “Hey, these 19 songs are problematic, and you’re going to have to figure out something else.”

RUDOLPH: Did you have to take those out?

QUESTLOVE: Oh, no. I refused to take no for an answer. One particular lawyer was rather unhappy with me about my disposition on one of his clients in the press, and I kind of had to get on a plane and travel hat-in-hand to this person and grovel. I sat there for a four-hour lecture, all so I can clear a four-second patch.

RUDOLPH: You knew it was coming though, right?

QUESTLOVE: I didn’t know it was that level. Eminem’s a great example. You got to deal with Eminem, then you got to deal with Dido’s people, then you got to deal with DJ Mark The 45 King, who just passed away, and sometimes when people pass away their estate really isn’t getting it together yet. So my approach to a Billie Eilish or a Taylor is to show them the clip and say, “Look, this is history, and I don’t think you want to get left out.” That turned all those 19 no’s into a yes. The one person that I couldn’t sway was when I wanted to add Luciano Paparotti to the Bobby McFerrin Busta Rhymes TLC mix, but I couldn’t fly to Italy.

RUDOLPH: That’s what Zoom is for.

QUESTLOVE: I know.

RUDOLPH: I was going to ask, is there a major regret that you were like, “I tried, but I couldn’t get”?

QUESTLOVE: To me, the most important part was making two sworn enemies duet with each other. And the fact that Prince’s “Party Up” and Rick James’ “Super Freak”—

RUDOLPH: You think I didn’t notice that?

QUESTLOVE: You were the reason why I put it in there. I was thinking of you and Fred. For me, it was about the winks to all my friends. Like, “Oh my god, this is happening.” How do you give a shout-out to people without saying their names?

RUDOLPH: It’s so good. There’s just so many winks. There’s only one person who’s not AI that could have done this, and you did it. There is no one else that would’ve been able to do this. End of story. This came completely out of your brain and your heart. It’s so evident that it’s made by a person who has lived through these performances and understands the larger picture of the show. Are there going to be other opportunities? Yes. But what do they mean to you? I don’t even know if you can help yourself not put those songs together in your head.

QUESTLOVE: I’ll never. I’m always thinking of music. 

RUDOLPH: This feels so handmade with love and care and knowledge exponentially beyond the way that other people hear music that you’re going to be opening people’s minds to how to understand music. People are probably going to be doing thesis papers on this.

QUESTLOVE: Thank you, Maya Rudolph. I appreciate that. And thank you for taking your time out to interview me.

RUDOLPH: I’ve never been happier. But I do think it is important to end on the fact that me and Jack White are just like Edie Brickell and Paul Simon. I mean, that’s just how this ends.

QUESTLOVE: That’s all that matters. Mic drop right there.