Madonna, meanwhile, has been a Britney supporter since the beginning, paying tribute to her music, calling for an end to her 13-year conservatorship and standing up against those who pit the two pop icons against each other.
Over the years, the duo have shared a number of sweet moments, from gushing over each other in interviews to performing and releasing music together. While there are too many Britney and Madonna memories to count, we’ve compiled nine of our favorites.
See them below, in chronological order.
2001: Madonna says she wears Britney Spears t-shirts to bed
“[She] just bowls me over. I love Britney,” Madonna told the New York Post back in 2001. “I want to do nothing but support her and praise her . . . I mean, she’s 18 years old. It’s just shocking. I wish I’d had my s— together when I was 18.”
“We’re different – apples and oranges,” she added. “[But] I became obsessed with wearing Britney t-shirts. I slept in them, as well. It was like I felt it would bring me luck. And it did.”
Madonna wearing Britney Spears t-shirts was pretty iconic pic.twitter.com/OQdZTBNViR
— )I( (@drownedtheo) December 13, 2020
2001: Britney sings “Like a Prayer” during interview
“I remember when I had the little Madonna skirts and I put the gloves on — I still do that now!” Spears said in a recently resurfaced interview from 2001. “Everybody wants to be Madonna! She doesn’t care what other people think. I think that’s very empowering for teenagers and women in general, to not try to please anyone except yourself.”
The then-20-year-old pop star then went on to briefly sing the opening verse of Madonna’s “Like a Prayer” a cappella.
2002: Britney Dances to “Open Your Heart” in Crossroads
Spears continued showing her love for Madonna — this time on the big screen. In her debut film, Crossroads, her character Lucy Wagner dances around her bedroom in her underwear, singing along to “Open Your Heart.”
2003: The pop icons collaborate on “Me Against the Music”
The song, off Britney’s 2003 album In the Zone, peaked at No. 35 on the Billboard Hot 100 chart dated November 29, 2003. The collaboration remained on the chart for a total of 13 weeks.
2003: The infamous VMAs kiss
Madonna then surprised everyone by kissing Spears onstage. After a quick camera cut to the pop princess’ ex-boyfriend, Justin Timberlake, Madonna then smooched Aguilera. But it was the Britney-Madonna kiss that made news.
2021: Madonna Lip Syncs to “…Baby One More Time”
Madonna took to Twitter to share a lip-sync video set to Spears’ 1998 breakout hit “…Baby One More Time,” captioning the video: “Love This Song……..,Love The Girl who sings it.”
— Madonna (@Madonna) April 8, 2021
2021: Madonna fights for Britney’s conservatorship to end
At the height of the #FreeBritney movement, Madonna advocated for an end of Spears’ 13-year conservatorship, which was officially terminated by a Los Angeles judge in November 2021.
Over a photo of herself wearing a Britney t-shirt, Madonna wrote: “Give this woman her life back. Slavery was abolished so long ago! Death to the greedy patriarchy that has been doing this to women for centuries. This is a violation of human rights! Britney we coming to get you out of jail!”
"We coming to get you out of jail"
— Madonna Daily (@madonnaxdaily) July 9, 2021
January 2022: Britney dances to Madonna’s “Nobody’s Perfect”
Britney kicked off the new year by sharing another one of her beloved dance videos to Instagram, spinning around in a red crop top to Madonna’s 2000 song.
In a follow-up post the next day, the pop princess revealed, “I’m sure it looks weird me dancing to @madonna so much … I see it … it’s like I’m not trying as much like I’m INDULGING ….. well thats exactly what her music does to me !!!”
2022: Madonna says she wants to go on tour with Britney and reenact VMAs kiss
In an Instagram Live session, Madonna was asked if she would ever do a world tour again. “Hell yeah, I have to,” she replied. “Stadium, baby. Me and Britney, what about that? Yeah, I’m not sure she’d be into it, but it would be really cool. We could, like, reenact the original kiss.”
Madonna wanna do a world tour with Britney pic.twitter.com/s1IWuHF0hH
— MADONNA IS MY MOM (@Fishyboi95) January 26, 2022