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Questlove couldn’t believe his eyes.
Two years into The Roots’ run as house band on Late Night With Jimmy Fallon, the legendary drummer stared at a calendar of the show’s upcoming musical guests. One name in particular jumped out at him, and he kept re-reading it over and over.
That couldn’t be right, he thought. For months, the rap collective had been buzzing on blogs and internet message boards, attracting a cult following thanks to the wild charisma of ringleader Tyler, the Creator. But a performance slot on an NBC show? At this early stage in their career? No way. It had to be a mistake.
“I went to our talent booker Jonathan Cohen and asked, ‘Is there some alternative Brooklyn band named Odd Future that you booked?’” Questlove says, remembering his disbelief. “He’s, like, ‘No, it’s this rap group from L.A.’ And my heart just stopped.”
According to Jimmy Fallon, a writer he used to work with on Saturday Night Live named Matt Murray told him about the crew a few weeks before. At the time, Fallon’s friends often suggested up-and-coming acts who they thought might be good for the show, so he went online and checked out some of the crew’s early self-released projects, like Bastard and The Odd Future Tape.
“I listened to it, and I thought, ‘Wow. This is so different. Let’s try to find these guys,’” Fallon says. “Our booker was like, ‘OK, but they’re not signed or anything.’ And I didn’t totally know how that worked, but I was like, ‘Who cares? If they’re good, let’s do it.’ So we booked Odd Future.”
At 8:04 p.m. on Jan. 31, Tyler made the announcement on Twitter: “Hodgy and I will be on Jimmy Fallon; oddfuture.com.” Less than one minute later, he added, “I want to scare the fuck out of old white fucking people that live in middle fucking America.”
The tone was set.
A self-made flyer, depicting Jimmy Fallon with fangs and cut-out eyes, started making the rounds online. Fans on Reddit replied with comments like “uh oh” and wondered how the notoriously rebellious crew would translate to network television. “I hope this doesn’t backfire,” one wrote.
“My first thought was, ‘Yo, what if they try to pull off some rogue shit that’ll make them internet famous?’” Questlove laughs. “So I thought, like, ‘This is either going to come off nicely or this could be the end. Like, we could get canceled after only being on the air for two years.”
More than anything, though, he was excited. For years, Questlove felt as though hip-hop had been missing something that Odd Future was finally bringing to the table. “I kind of made a public declaration that hip-hop really wasn’t exciting anymore and that danger element [was missing],” he remembers. “I thought the whole, ‘This is who your parents warned you about,’ element of hip-hop really left after 50 Cent. But when Odd Future were doing those early mixtapes, there was a sense of danger.”
Hoping to establish Late Night as the show that every exciting up-and-coming artist wanted to appear on, Questlove had been waiting for an opportunity like this.
“For me, it was like, can we use [The Roots’] cool factor to make this show cool?” he says. “There wasn’t a late night show that was really cool, like, ‘I’ve got to get on the show.’ And by this point, we were in our second year and I was still waiting for that paradigm shift. I hoped to get to the point where people wanted to come on our show, and not the show that came on right before it. It turns out that defining moment was Odd Future.”
“I thought the whole, ‘This is who your parents warned you about,’ element of hip-hop really left after 50 Cent. But when Odd Future were doing those early mixtapes, there was a sense of danger.” – Questlove
Watching Odd Future’s early performances reminded Questlove of Bad Brains concerts, and he wanted to bring that punk rock energy to a broadcast television stage. He had memories of Bobcat Goldthwait setting The Tonight Show couch on fire, and he half-expected a “rogue moment” like that would happen when Tyler and Hodgy took the stage. So, he spent the rest of the week avoiding the topic of Odd Future whenever he spoke with Fallon. The two would normally engage in banter about upcoming musical guests, but Questlove was afraid he would let something slip, like, “You know these guys are crazy dangerous, right?” and make the host second-guess his decision. He remembers thinking, “This is some real shit that’s about to happen, and I don’t know if they know what they’re about to get into.”
He shouldn’t have been worried. It turns out Fallon was actively looking for cutting-edge new artists like Odd Future to book on the show. “We love music, and we actually love new stuff,” he points out. “We love that punk of it all.”
A few days before the show, Tyler, Hodgy, and the rest of Odd Future flew into New York City. “We stayed in a bed and breakfast,” says documentarian Brick Stowell, who was traveling with the crew as a photographer and road manager at the time. “We did not stay in a nice hotel at all. From the moment we got there, it was just batshit crazy.”
One of their first stops in the city was at a nightclub called Santos Party House for a sold-out show where Tyler yelled things like, “I just wanna slap the fuck out of all parents and bloggers!” According to Stowell, they also killed time by riding around the city in a passenger van, making stops at streetwear stores like Supreme, and visiting Terry Richardson’s photo studio.
On the day of the performance, a group of enthusiastic Odd Future fans showed up to 30 Rockefeller Plaza, with hopes of witnessing the performance firsthand. Fortunately for them, Late Night had a policy of setting aside at least 100 tickets each night for fans of the episode’s musical guests. One of those fans even arrived with an article of Tyler’s clothing.
“Tyler lost one of his blue Vans at the Santos show, and he didn’t want to buy new shoes because he only wore those specific Vans in that colorway,” Stowell remembers. “But the kid who got his shoe at Santos actually showed up and gave it to Tyler before the performance. We were like, ‘Wait, what? How did that just happen?’”
“In my mind, I’m like, ‘Oh, this is the moment where he’s going to punch Jimmy out on national television.’” – Questlove
Backstage, powerful label executives like David Airaudi, Caius Pawson, and Richard Russell milled around in the greenroom, and they weren’t the only VIPs on set. All three members of The Lonely Island walked over from the SNL set to catch the performance, and Yasiin Bey (known as Mos Def at the time) even showed up, unannounced. Yasiin wasn’t a guest on the show that night, but he was already a fan of Odd Future and had an inkling their Late Night set was going to be a historic moment, so he made some calls to get a spot on the guestlist.
“I’m like, ‘Wait a minute—as many times as I asked you to show up to a concert or something, it’s always a no-show,’” Questlove laughs, recalling the surprise he felt when he spotted his longtime friend and collaborator backstage. “But somebody put you on the list to come here today, and it wasn’t me.”
As showtime neared, Tyler couldn’t help but have some fun when he finally met the host of the show. “I walked up and introduced myself, like, ‘Hey, Tyler. How’re you doing? This is Jimmy,’” Fallon says. “And he responds in a very quiet, hoarse whisper: ‘Thanks so much for inviting me. I’m excited.’ And I go, ‘Oh no, this guy lost his voice. This is the worst thing that could ever happen.’ Then he goes, ‘No, no, I’m just playing.’ I’m like, ’What?! Who is this dude? [Laughs.] What is he talking about?’”
Moments later, Questlove also had a surprising interaction with Tyler. “The weirdest thing was, Tyler instantly disarmed me with—of all things in the world—a conversation about Justin Bieber,” he says. “The Biebs had been on the show recently, so Tyler kept asking me, ‘What’s he like, man? You’ve got to tell me about Biebs, man. What was that motherfucker like?’ And I thought he was trying to troll me. But 10 minutes into the conversation, I was like, ‘Wait a minute. You really do like Justin Bieber!’ I was so used to hipster irony and all that stuff that I didn’t even realize he’s post-millennial. If Pharrell defined millennials, then I feel like Tyler defined Black Gen Z. So I realized during the conversation, ‘Oh, he’s really a nerd.’ He was asking all these music questions and asking them in a way where he just had no fear.”
Fallon says he approved Odd Future’s unusual request for garden gnomes and a creepy girl to appear onstage with them, without giving it a second thought. “People would always make these weird requests, like, ‘Hey, do you mind if I drink a glass of milk and eat a peanut butter and jelly sandwich during the song?’” he points out. “I’d go, ‘I couldn’t care less. Love it. Go for it, if that’s your thing.’ So they wanted the dead girl and some garden gnomes and I said, ‘Sure. Go for it, man.’ I don’t know if they danced or sang or what.”
Meanwhile, Questlove says he was “being super anal retentive to our sound engineer to make sure that the patches and the gates and the keyboard sounds exactly matched the record.” At that point in the show’s run, he was tired of artists coming in with requests to “Roots-ify” their songs, and he didn’t want to overplay anything. He says he wanted to “make sure the sound was spot on and as dark and as crazy as possible,” and admits, “I just didn’t want the millennial rejection of ‘Nah, man. That ain’t how the record sounds.’”
Questlove also reveals Tyler had a last-minute request for The Roots: “I definitely remember him being like, ‘Yo, y’all can’t wear these suits. Please don’t wear those suits.’ So, just 20 minutes before show time, the band scrambled and ended up grabbing hoodies that were supposed to be used as tour merch and threw them on instead.”
“When I was watching them trend in real time, the first person I called was Jay-Z. And I was like, ‘Yo, I found your Wu-Tang.’” – Questlove
Then, seconds before taking the stage, Tyler posed one more question. “Yo, I can go over to the desk?” he asked Questlove, who didn’t know how to respond. “In my mind, I’m like, ‘Oh, this is the moment where he’s going to punch Jimmy out on national television,’” the drummer reflects. “I was just waiting for one of those rogue Tracy Jordan 30 Rock moments. I’m thinking, ‘Damn, if you say no, he’ll do it anyways, and then you’ll be the authority figure that is square. But if you say yes, then you’ll get fired.’ I think I copped out and just said something real hip-hop like, ‘Yo, dog, do you.’ [Laughs.]”
When the performance finally began, the room filled with smoke as Hodgy and Tyler performed the opening verses of “Sandwitches” with ski masks pulled over their faces. “When they came out wearing ski masks, I go, ‘Oh, no, no, no. This is off the rails,’” Fallon laughs. “I didn’t know what was going on, man. But I’m sitting there, playing my part as the host, wearing a suit and tie. That’s what it should be: You’re the artist, I’m the host, so just go for it.”
Forced to adapt the song’s explicit lyrics for a network television audience (“Who the heck invited Mr. I Don’t Give a What?”) Tyler still managed to bring the dangerous energy Questlove had hoped for, as he growled into his microphone. And by the time they made it to the chorus and started yelling “Wolf Gang,” Tyler’s mask was off as he bounced around the stage. Moments later, at the end of Hodgy’s verse, things really did go off the rails as Tyler sprinted toward Fallon’s desk, where the host sat with the episode’s celebrity guests: Brandon T. Jackson and Felicia Day.
“Man, when he went to Jimmy’s desk, I remember [The Roots keyboard player] Kamal and I gave each other a look,” Questlove says. “I felt like it was going to be a Bugs Bunny, Elmer Fudd moment. Like, either he knocks him out with a hammer or he kisses him or something crazy.”
Instead, Tyler put his microphone in Felicia Day’s face and jumped over the couches. (“I remember that he was over the moon excited that he got her to say the word, ‘wolf,’” Questlove says. “Like, ‘Yo! She said wolf! She said wolf!”) When he made it back, the song ended abruptly, and Tyler and Hodgy ran backstage without a goodbye.
“I think they were so nervous, because it was their first time, that they left,” Fallon says. “Some bands do that. They perform, and then they think they’re kind of in trouble or something. They finish their song, and then they go, ‘All right, let’s get out of here.’ I remember even Kanye was nervous when he performed. He was like, ‘Can I do that one more time?’ I thought there were going to be people right in front of me. I didn’t know it was just going to be cameras.’
“So they left, and then I go, ‘All right, Odd Future everybody,’” he adds. “Sometimes I bend down to point behind me, like, ‘Give it up for The Roots.’ So I leaned down to point at The Roots behind me, and Tyler came back out and jumped on my back. I think he thought that I was saying, ‘Get on my back,’ or something.”
As Tyler wrapped himself around Fallon’s shoulders and put a Supreme hat on the host’s head, Yasiin Bey popped up in front of the camera and repeatedly yelled, “swag!” until the show cut to commercial.
Watching the scene unfold from the top of the studio stairs, Stowell could immediately tell how special the moment was. “They absolutely destroyed that performance and reset the idea of what a late night TV performance could be,” he says. Remembering sitting with other Odd Future members like Domo Genesis, Syd, and Matt Martians, Stowell adds, “It was just like, ‘Yo, your homies just won the World Series.’ We all looked at each other like, ‘Damn did they just really fucking do that?’ The energy in the room was ecstatic.”
“I never know what to do in those moments, but I love them, because it’s just awkward, dangerous TV. It was honestly as close as you can get to rock ‘n’ roll television.” – Jimmy Fallon
Anyone who was lucky enough to be watching at home witnessed one of the most raw, spontaneous moments of television from the past decade.
“I never know what to do in those moments, but I love them, because it’s just awkward, dangerous TV,” Fallon says. “It was honestly as close as you can get to rock ‘n’ roll television.” Questlove adds, “Mos yelling ‘swag’ at the end is what sealed the deal for me.”
“I remember the next day, it was all over the internet,” Fallon recalls, before Questlove points out: “I believe that that was the first time that we ever trended as a show.”
After the performance, Stowell says, “Everyone celebrated. We left, and went straight back to the bed and breakfast to watch the performance. We experienced it live, and then as soon as it was done, we were like, ‘Let’s go back to the hotel.’ Mind you, all these fuckers were like, 19. They didn’t want to do anything. They wanted to order pizza and go back to the hotel.”
Questlove was so fired up that he made sure to make a call to another rap legend right away. “When I was watching them trend in real time, the first person I called was Jay-Z,” he says. “And I was like, ‘Yo, I found your Wu-Tang. They’re this collective. They’re all-in-one, and you can grab them all.’ I was like, ‘Look, Frank Ocean’s Method Man. And it looks like when Earl gets out, he’ll be Ghostface.’ I was just trying to tell him this is the new Wu-Tang. Get them now before Kanye beats you to it and starts co-signing them. And he took my advice. I definitely know that he met with Tyler like a week later on my recommendation.”
Soon after, Questlove showed up to Odd Future’s performance at the Highline Ballroom and saw the Wu-Tang connection unfold firsthand. “I was backstage and the only adults there were me and the GZA from Wu-Tang Clan. His excuse was, ‘Well, my two teenage sons are down with Tyler, so that’s why I’m here. Why are you here?’ And I was just like, ‘The last time I felt this type of genuine excitement and danger in the air at a rap show was seeing you guys back in 1993.’”
That night proved to be a turning point for the show, helping to establish Late Night (and later, The Tonight Show Starring Jimmy Fallon) as the go-to place for cool new musicians to have breakout moments on national TV. “I think people noticed we were ready to break new people and do something different,” Fallon says. “As long as you put a good show on, it can pay off. I think you can see through the TV when you’re having fun, so if we just have fun, that’s the way we should book the show.”
For the following decade, that mentality has embedded itself into the DNA of the show, leading to many landmark performances from emerging artists over the years. It also acted as a watershed moment in the convergence of internet culture and traditional mainstream entertainment. Network TV shows like Late Night proved that taking a risk on talent that was bubbling online could pay off in a big way.
“I definitely feel as though that moment was the defining moment of the show,” Questlove notes. “We took advantage of viral culture, and most people watch the show the day after on the internet, so there’s a level playing field and the floodgates of cool just came spilling out. That was the moment I was waiting for. Now it’s like, everybody wants to come on the Fallon show because that was such a viral, cool moment that everyone talked about in the press.”
The performance also spawned personal relationships that last to this day. Questlove reveals he routinely has conversations about music with Tyler, even gifting him with a drum kit last year.
“That was the moment I was waiting for. Now it’s like, everybody wants to come on the Fallon show because that was such a viral, cool moment that everyone talked about.” – Questlove
Stowell, who first met Odd Future in 2010 and finessed a rare photo shoot with the crew after bonding with Tyler over his Supreme baseball jersey, developed a close collaborative relationship that extended long after that 2011 trip to New York. Shooting photos, album covers, magazine spreads, and more, he became an integral member of the crew for much of the early part of the decade. (“I owe those boys everything, literally,” he says.) Even after entering the food arena as a consultant in recent years, Stowell has stayed in close contact with Tyler, who took the press photos for his new restaurant Burgers 99. Through it all, though, that day on the set of Fallon 10 years ago remains a clear highlight.
“For me, as a documenter and rolling around with the band, it was one of the cooler moments of that whole era,” Stowell says now. “Nothing was calculated. It was all organic, coming from the minds of Tyler and Hodgy Beats. And it’s very interesting to see their influence on modern musicians now. Those dudes just broke the mold. They were doing things that your average musicians weren’t doing at that time. The style, the look, the whole vibe… it was punk rock.”
Even Jimmy Fallon, who has witnessed hundreds of performances in over a decade as host of Late Night and The Tonight Show, says he’ll forever feel a special connection with Tyler because of what happened on Feb. 16, 2011.
“I love those moments because you go, like, ‘Yeah, we’ll always have that, man,’” he says. “Tyler sticks out the most for me, though. When I see Tyler, we always have a little nod of, like, ‘We were there! We remember.’”