Tom Holland Broke The Internet By Performing In Drag While Playing It Straight

Thanks to the success of Spider-Man: No Way Home, Tom Holland has been trending on social media again. And every time this happens one of my favorite television moments of all time starts circulating: Holland’s now legendary appearance on Lip-Sync Battle.

Holland was competing against costar and future girlfriend Zendaya. The first round was fine. Holland covered Ride Wit Me by Nelly while Zendaya tackled Erica Badyu’s Tyrone. But diehard fans know that Lip Sync Battles are really won in the second round, when contestants are encouraged to dress up like the artist they are mimicking and perform elaborately choreographed numbers – complete with backup dancers, props, and sets. 

Zendaya went first, and absolutely killed performing 24K Gold by Bruno Mars. Then it was Holland’s turn. He started with a tap-dancing performance of Gene Kelley’s Singing In The Rain – then suddenly after a brief record scratch, Holland was singing Umbrella while decked out in a spaghetti-strap top, hot pants and fishnets; duplicating Rhianna’s look from the music video perfectly down to the lipstick and hairstyle.

On Lip-Sync Battle, one surefire way for men to get the crowd behind them has been to show that they have a sense of humor by crossdressing and lip-syncing to a song by a female performer. Krasinski started this trend way back in the fourth episode of season one, turning in his rendition of Tina Turner’s Proud Mary while shaking and shimmying in Turner’s classic fringe dress. He beat Anna Kendrick and future male contestants took note. Crossdressing men became a staple of the show, perhaps peaking when Channing Tatum appeared a few years later with a goofy take on Elsa’s Let It Go, complete with princess gown and wig. 

Holland didn’t do what so many of the male performers had done before him. He was not dressed as a woman in order to show he had a sense of humor or to act goofy. He dressed as Rhianna because Rhianna is a badass and he did his best to channel her energy while on stage.

The real difference between Holland and most other male performers who dressed in drag on the show was – for lack of a better term: Holland played it straight. 

This is a giant step past men “willing to make fun of themselves.” This is acknowledging that emulating women can be empowering. It’s affirming that women have value and that men dressing as women can be more than a joke. 

Whether they are conscious of it or not, I think this is why so many women return to this particular lip-sync performance again and again. Because in it, Holland shows that he thinks women are more than a joke. They are people that men can admire and emulate.

In a patriarchal world that has equated femininity with weakness, Holland is a hero.

PS – I would be remiss if I didn’t mention the other great performance of a woman’s song by a male actor: Joseph Gordon-Leavitt’s amazing, choreographed rendition of Janet Jackson’s Rhythm Nation — included below for your enjoyment.