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Orgo-Life the new way to the future Advertising by AdpathwayZendaya and Tom Holland Are Engaged
Tom Holland and Zendaya's engagement news is certainly a challenger for the biggest moment in their relationship so far.
But that's not the only moment that will live in fans' hearts forever. In honor of the couple taking the next step in their romance, it felt only right to revisit another unforgettable Tomdaya memory: when the pair faced off on the Lip Sync Battle.
For the iconic 2017 episode, both Zendaya and Tom—who met during the screen test for their 2017 film Spider-Man: Homecoming but didn't confirm their romance until four years later—brought their all to their performances.
Kicking off the legendary show, the Euphoria actress looked nearly unrecognizable dressed as Bruno Mars to perform his hit "24K Magic," rocking a short-haired wig, oversized sunglasses, a fitted hat and a matching shirt-and-shorts set. And her dance moves were equally as impressive, with Zendaya even taking a break to rain dollar bills on Tom's head.
But while the Emmy winner—who showed off a diamond ring on that finger while walking the red carpet for the 2025 Golden Globes on Jan. 5, one day before her and Tom's engagement news broke—certainly wowed the Lip Sync Battle audience, it was Tom who wound up taking home the win for his mashup performance of Gene Kelly's "Singing in the Rain" and Rihanna's "Umbrella."
The Crowded Room star made jaws drop when he stripped down to a corset top, sequin shorts and fishnet tights to perform a sultry routine with an umbrella. And he received even more uproarious applause when he concluded his epic dance with rain falling down on him, leaving him soaked and on the floor for his final pose.
Since then, Tom has admitted that his show-stopping performance gets him the most compliments from fans.
"That Lip Sync Battle is kind of one of those things that has kind of come back to haunt me a little bit," the 28-year-old told Entertainment Weekly in 2022. "I get more compliments from dancing in the rain in fishnets than anything [else] I've done."
Albert L. Ortega/Getty Images
And Zendaya, also 28, isn't surprised by that attention. After all, she's willing to admit that her fiancé deserved the win.
"He did so good," she told MTV UK in 2018. "I was like, 'OK, you can give it to him.'"
For more times Zendaya and Tom's romance was nothing short of euphoric, keep reading.
Alberto E. Rodriguez/Getty Images for Disney
July 2016: Comic-Con Fun
Tom Holland and Zendaya shared a laugh during the Marvel panel event at San Diego Comic-Con International 2016 in San Diego, Calif, ahead of the release of Spider-Man: Homecoming.
Kevin Winter/Getty Images
May 2017: MTV Movie & TV Awards
The Spider-Man: Homecoming stars spoke onstage at the award show in Los Angeles.
Gabriel Maseda/NurPhoto via Getty Images
June 2017: Promoting in Spain
Tom and Zendaya attended a photo call for Spider-Man: Homecoming in Madrid.
Kevin Winter/Getty Images
June 2019: Par-tay
The duo appeared at the after-party for the premiere of Spider-Man: Far From Home in Hollywood, Calif.
Tom Holland/Instagram
September 2021: Birthday Shoutout
Months after their romance was confirmed, Tom gushed over his onscreen and offscreen girlfriend.
"My MJ, have the happiest of birthdays," he wrote, referring to Zendaya by her character's name, in his Sept. 1 post. "Gimme a call when your up xxx"
David M. Benett/Dave Benett/WireImage/ Karwai Tang
December 2021: Back to London
The two attended a photo call for Spider-Man: No Way Home at The Old Sessions House in London.
Cindy Ord/Getty Images for SiriusXM
December 2021: Promoting Spider-Man: No Way Home
Tom and Zendaya spoke during SiriusXM Radio's Town Hall with the cast of Spider-Man: No Way Home in New York City.
Albert L. Ortega/Getty Images
December 2021: Spider-Man: No Way Home Premiere in L.A.
The actress, in a custom Valentino gown, and Tom, in a Prada suit, posed for pictures at the premiere of Spider-Man: No Way Home in Los Angeles.
Zendaya/Instagram
December 2021: Celebrating a Dream Fulfilled
After their third Spider-Man film hit theaters, Zendaya heaped praise over her leading man.
"My Spider-Man, I’m so proud of you," she gushed, "some things never change and good thing @tomholland2013."
Gotham/GC Images
February 2022: Taking in a New York Minute
The duo dressed to impress as they enjoyed a belated Valentine's Day night on the town in NYC Feb. 16.
June 2023: Tom's 27th Birthday
Zendaya shared this sweet shot of her boyfriend enjoying the water in honor of his birthday.
June 2023: Tom's "Sexiest" Pic Ever
Tom unveiled this beauty for his 27th birthday, joking on Instagram, "A gift from me to you. I thought I'd share possibly the sexiest picture ever taken of me!" Zendaya was into it, reacting with a heart-eye emoji.
Matthew Stockman/Getty Images
March 2024: Acing a Tennis Date
Zendaya channeled her inner Tashi Duncan ahead of her movie Challengers' release during a tennis outing with Tom and her longtime assistant Darnell Appling at the Men's Final of the BNP Paribas Open in Indian Wells, Calif.
Splash by Shutterstock
April 2024: All Smiles
The two enjoyed a night out in London.
Ricky Vigil M / Justin E Palmer / Contributor / GETTY IMAGES
May 2024: In Fair Verona
Zendaya supported Tom after the debut of his play Romeo and Juliet in London, where the pair were seen holding hands following the show.
XNY/Star Max/GC Images
October 2024: Bero Launch Party
As Tom debuted his non-alcoholic beer company, Bero, Zendaya was by his side in a coordinating burgundy look.
Tom Holland/Instagram
November 2024: Low Key Date Night
While visiting Zendaya in Newbury, Massachusetts, where Zendaya was filming her movie The Drama, the duo popped out for a pint of Bero.
“I’m heading out to a bar to have my first Bero in the wild,” Tom, wrote on is Instagram story alongside a shot of his longtime girlfriend smiling in the background. “I’ll let you know how it goes.”
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