An oral history of Tom Holland's sensational 'Lip Sync Battle' performance

The year was 2017. The Oscars had mixed up their winners. Kendall Jenner had made a problematic Pepsi ad. The Fyre Festival had crashed and burned, sad cheese sandwiches and all.

And then came Tom Holland's "Lip Sync Battle" mashup of Gene Kelly and Rihanna, or what is essentially two minutes and 10 seconds of perfection in every sense of the word. Ditching his initial top hat and suit to grind on a literal umbrella and perform a sensual routine in a pleather leotard, red lipstick, and chin-length wig, the British actor, then 20, obliterated gender constructs and defied the expectations of how a newly minted action star should market himself.

When he appeared on the May 7 episode with his friend and "Spider-Man: Homecoming" co-star Zendaya, Holland had already played Spider-Man in 2016's "Captain America: Civil War." But "Homecoming," set for release 2 months later, would be his first leading role as the superhero. "Lip Sync Battle" would be part of his first major publicity tour, and, for many Americans, their first introduction to Holland.

The first three performances of the fateful episode - Zendaya's takes on Erykah Badu's "Tyrone" and Bruno Mars' "24K Magic," plus Holland's version of Nelly's "Ride Wit Me" - are powerful in their own right. And the show itself, which was in its third season, was an institution: it had attracted guests like Anne Hathaway, who swung from the ceiling on a giant wrecking ball, and Channing Tatum, who strutted to "Run the World (Girls)" with the actual Beyoncé.

But it was Holland's show-stopping choreography that would win him the mantle of the most famous, and beloved, routine in the show's history.

TikTok is full of dancers recreating his "Umbrella" choreography. Clips of the routine go viral with soothing regularity. Holland's "Spider-Man" co-star Jacob Batalon wore a hoodie emblazoned with a caricature of Holland mid-routine. (You can buy your own on Etsy.) Nary an interview goes by where Holland isn't asked about his performance.

"That 'Lip Sync Battle' is kind of one of those things that has kind of come back to haunt me a little bit," Holland told Entertainment Weekly earlier this year. "I get more compliments from dancing in the rain in fishnets than anything [else] I've done."

Below, to celebrate the episode's 4th anniversary, those who worked on it - including producers, choreographers, writers, and dancers - reveal to Insider how the seminal moment in pop culture history came to be. (A representative for Holland told Insider that he was "respectfully declining interview requests for the near future." Representatives for show host LL Cool J and co-host Chrissy Teigen declined requests for comment. Representatives for Zendaya and Rihanna did not respond to requests for comment.)

Sony approached the "Lip Sync Battle" producers with the idea of doing a Holland vs. Zendaya episode to promote 'Spider-Man: Homecoming' ahead of its July 2017 release.

Casey Patterson, executive producer: I really think it was in keeping with how they were positioning "Spider-Man" at the time, which was: It's all new. It's younger. They wanted to introduce Tom to an American audience in that spirit. They loved the idea that they could show how multi-talented he is because you're going to see the physicality in "Spider-Man," but you really get to know someone when they come to "Lip Sync Battle."

Danielle Flora, choreographer: At that time, we would say, "Okay, here are our celebrities that are coming in. This is what they listen to, this is their music list." And then me and some of the writers would pitch ideas to Casey and talk her through how we visualized it.

Patterson: Tom has such great taste in music, and we kicked around a lot of ideas, but we pitched him "Umbrella" because we thought we could do "Singin' in the Rain" in the beginning and it would just be a great way to show off the "Billy Elliot" side of him, too. He was fearless. He was like, That's it. That's absolutely it.

Flora: My process is creating ideas and hoping that whoever my celebrity is, maybe they'll be able to dance a little bit and perform a few counts sprinkled throughout the number. I had no idea when Tom walked in that he was going to be able to do everything and then some.

Patterson: There was a little bit of like, "Casey, what have you done?" kind of thing [from Sony]. "You got Tom super excited about this big, risky idea." But it was just so organic. He's speaking to an audience who wouldn't think twice about him doing a Rihanna song and doing it in tribute to exactly the way that she did it in the video.

Every song performed on "Lip Sync Battle" has to get cleared by the artists and songwriters involved in the track. Once the show decided on "Umbrella," it wasn't certain that they could get the rights. Britney Spears' "Oops I Did It Again" was prepared as a backup, and, according to the creative brief viewed by Insider, would have involved Holland dressed in the classic red latex jumpsuit and a possible cameo from Spears in costume as an astronaut.

Patterson: We would clear song by song and have to go to each artist. We'd say we have Tom Holland coming on the show, and Rihanna would need to bless it. It's never a given.

Jeanie Cheek, costume designer: We actually created two different sets of costumes for him and all of the dancers. Just in case "Umbrella" didn't go through, we had a backup performance.

Flora: I don't remember [the backup Britney song] at all. I'm sure I choreographed it. And I'm sure that it was traumatic for me at the moment, choreographing two numbers and not knowing which one. I think we always wanted it to be "Umbrella."

Kuk Harrell, "Umbrella" co-writer and producer: That [licensing] stuff always goes through the publisher, and then they just logistically reached out to us and asked if we would like to grant permission for "Umbrella" to be used. I did not know who Tom Holland was.

Tricky Stewart, "Umbrella" co-writer and producer: It was just like, "Are you okay with it or not?" And, obviously, "Lip Sync Battle," it's like a notch in your belt to have a song that is so known that people would actually be able to lip sync it. It's a great feeling.

Patterson: The minute "Umbrella" [got approved] it was just immediate, unanimous. We were high fiving, like, "That's it. The world's going to go crazy."

Holland's performance required two distinct looks: a suit-and-tie ensemble for the Gene Kelly "Singin' in the Rain" opener, and a French maid-inspired look from the "Umbrella" music video for the main Rihanna segment.

Baza Novic, prop master: My main focus and responsibility was Tom not getting hurt by any of the dynamic props and staging elements. I didn't want to be the one responsible for injuring Spider-Man.

Marvin Brown, dancer: My first reaction was, "is he going to dress as Rihanna?" That's what we were all excited about. And then in the first rehearsal he was like, I'm going to come out and sing 'Singin' in the Rain.' And we all just thought, "Oh no, that means you're going to be [dressed like] a guy for the rest of it." And he was like, No, no, no, I want to do a quick change.

Cheek: We actually took a real suit and a real shirt and a real tie, and instead of him having all of those layers, we essentially cut them apart and stitched them together to make one garment. [It] could tear off and come apart right down the middle.

Patterson: We weren't sure if he would go all the way with the wardrobe. This was one of his first looks on American TV. Are you going to go all the way there? And he totally and completely was like, Yes, why do it if you're not going all the way?

Novic: The prop buyer had to scour downtown L.A. to buy out all the umbrellas she could muster [for Tom and the dancers]. In retrospect, I sure hope it didn't rain in LA that weekend, as we gobbled up all the black umbrellas we could find. Tom ended up using the one that he had brought with him.

Cheek: We picked the French maid look because it was the most different from the suit. A man in a suit to a French maid costume is pretty dramatic. We knew that the outfit underneath was going to be tiny and it was going to be tight. It was built like a leotard, all one piece.

Brown: Once we knew that he was going to be in the Rihanna look, we were like, "Okay, this is about to be the performance of the night."

Cheek: In the beginning, we had made the little lace cuffs that he had around his wrists much bigger and fluffier, and he asked us to make those a little bit less pronounced. That actually worked out really well because it was much easier to hide those underneath the sleeves of the suit.

Flora: I think he definitely could have done the routine in heels. I don't think he would have been able to do what he did in the water. I think it would have been less dancing and a little more stomping around.

Holland spent the days leading up to the taping working on his routine with Flora and the backup dancers, but, according to the crew, he didn't do a full dress rehearsal until the same day as the taping. Nevertheless, his background in performance - he starred in "Billy Elliot the Musical," and trained in dance - helped immensely.

Flora: Every agent says that their celebrity guest is a great dancer. Then, when they show up on set, it just really is never the case. So, this was the most beautiful blessing. It's like this wonderful human has fallen out of the sky and on top of that, he really can dance his butt off.

Patterson: I think we reached out to Rihanna [to cameo in the performance] at some point, and it was always [a] scheduling [issue]. She was super supportive of the show.

Flora: We showed Tom the choreographed performance, and then I said, "Anything you don't like, anything you want to add, we can change it." And he was like, Oh my God. I'm in. I can do it all.

Patterson: He was so devoted, he wanted extra time to come in and work with the dancers. He really leaned in, no hesitation, didn't flinch.

Jana Krumholtz, dancer: I have a big background in tap [dancing] and so I was like, "I'll help with the tap opening." But he didn't need any notes. I was like, "Yeah, I've got nothing for you. You nailed it." He took it so seriously.

Flora: He picked up the choreography so fast. Then, he wanted to get those little nuances perfect. So, for instance, the rolling of the hips or the hips being pushed up, those accents are a little more feminine than maybe the way he would just naturally do them. So, it was just fine tuning that.

Brown: We honestly didn't get to do Tom's routine properly until the morning of the show. That was the only time we actually got to do it with water and every effect because of the budget.

Cheek: We only did one dress rehearsal with the body suit because then it had to dry.

Flora: Dancing in water, it's scary because it is slippery. There was a moment in rehearsal where we did it with the water for the first time, and he slipped a little bit when he did that flip at the end, and I was like, "Oh, god. I'm going to lose my job. I killed Tom Holland." But he was adamant about it. He was not taking it out.

Brown: Tom's was the most challenging routine I worked on. They were constantly adding things to make it a little bit more difficult every time, and Tom was the kind of the person who never said no. He would make it harder for himself.

Patterson: As nervous as he was right before the show, he kept adding. He'd say, Oh, I have an idea. Like, Can I stage dive?

Brown: He wanted to go out in the crowd and we were like, "You can't do that!" He wanted to do too much.

Patterson: With both of him and Zendaya, it was the commitment. They went really hard for their fans.

Brown: Some actors when they come in, they're terrible. They have no idea what they're doing. But because of his performance background, Tom just knew exactly what he wanted.

Flora: It just makes such an incredible difference to have someone like Tom and Zendaya come and both be so gifted and want to actually dance. Not say, "I don't want to have to remember choreography because I don't want the pressure." They wanted the pressure, wanted their numbers to be hyped. They wanted all of it.

The episode was pre-taped in front of a live audience in early April 2017. Holland has since admitted it was one of the most nerve-wracking experiences of his life, and his dad tried to talk him out of doing it.

Flora: The one thing that has always been drilled in from Casey is it's a lip sync battle. It is not a dance battle. And because of that, a lot of times, you're really only shooting from the neck up. Obviously, as a choreographer, I wanted Tom to dance as much as possible. But I wasn't sure how that was going to play out [on camera]. Once you take a look at how gifted his dancing is, I think there was no other way to shoot it but to see the whole package.

Cheek: He did that performance in one take. We did not do a second take. We rarely do second takes, but they're not always as perfect and as seamless as that.

Flora: I was concerned about the fact that the light pole [used in the "Singin' in the Rain" opener] was not fixed. He couldn't really swing on it, so I was worried about his adrenaline and what that would do.

Novic: Tom's safety was everyone's concern. I personally hung on that pole from all angles [to test it beforehand].

Flora: It was fine, and then my biggest concern was the quick change.

Cheek: So, he runs behind the umbrellas to cover him up, [Flora] and her assistant are hiding backstage, they tear things off. He did the lipstick himself! Someone hands him the lipstick, and he did it himself. No mirror, no nothing.

Flora: The quick change wasn't foolproof. I think I was in charge of getting his pants off. Literally, there are four women back there. Each one of us has an umbrella. We're just ripping his clothes off. Thank god it all lined up.

Cheek: Those reactions that you see, when Zendaya's eyes pop out of her head when he comes out dressed as Rihanna? That was totally real.

Patterson: Those two are sneaky. I don't know how much they were talking. Zendaya wasn't supposed to know about the music, but if she did, she definitely didn't know about the pyro. She didn't know about the rain. She didn't know about the open.

Brown: Honestly, his performance was so perfect. We got off stage and we were just like, "What the heck? Why did that go so well?"

Novic: All I care about is that nothing, including the humans, breaks during the performance. This one ended with a very large sigh of relief.

Flora: I was ecstatic. We were all jumping up and down screaming at the side of the stage. It felt so good. I was really just so proud of it.

Patterson: He chose an ambitious song. He chose one of the biggest artists in the world. And he chose the most amazing way to do it. There's no way the audience wasn't going to be with him in a huge way for going that far for them.

When the episode aired on May 7, Holland's "Umbrella" performance instantly went viral. Holland has said he didn't hear from Rihanna afterward.

Harrell: I saw it live [when it aired]. Obviously, the performance was crazy. It was the energy that we put forth in making the song, producing the song, and how Rihanna performed the record. I think his performance really encapsulated all of that and gave everybody an opportunity to just love the song all over again.

Patterson: Tom was just so stunned. It really caught fire. He would text and just say like, Oh, my God, there isn't a day that goes by..., like, you can imagine his friends, people he's known, people he's performed with texting him that video every five minutes? Anne Hathaway said the same thing. She said she had more people wanting to talk to her after her "Lip Sync Battle" performance than when she won her Oscar. I think because it's so personal.

Stewart: This [clip] was all the way in mainstream America. That means that everyone knows the song when you get to the point where it can be utilized on a platform like ["Lip Sync Battle"]. It means you have done more than write a hit song - it's what we call a smash. It was a huge honor, and we were glad to be a part.

Four years later, Holland's "Umbrella" is still a part of the pop-culture conversation. The unofficial "Tom Holland Umbrella Law" holds that anyone who sees a clip of the performance on social media is obligated to reshare it, thus perpetuating an endless cycle. As Patterson put it to Insider, "'Lip Sync Battle' was one of the first shows to be a viral engine."

Patterson: After Tom's performance, we definitely saw talent wanting to raise the stakes and live up to what he'd done.

Krumholtz: He so fully embodied it and was celebrating Rihanna. You can feel his respect for the art. Doing Gene Kelly and Rihanna? It's brilliant to bring them both into one number.

Cheek: Even though he had a wig, even though he had a bodysuit, his dancing was still Tom and it was sexy. It was him really just getting into it and feeling the music. He wasn't trying to make it a parody.

Flora: There's a difference between playing a woman or totally trying to execute as a woman. And he just wanted to really execute it. There is a sense of humor in there, but he wasn't making fun at all.

Patterson: I think he loves us and curses us at the same time for how tied he will be to that performance forever. It's his fault. He killed it. He leaned all the way in like the pro that he is, and it went crazy because of that.

Ashley Spencer is an entertainment writer and reporter whose work has appeared in The New York Times, Vanity Fair, VICE, The Washington Post, and elsewhere. Follow her on Twitter at @AshleyySpencer.