Entertainment Music 14 of Justin Timberlake & Britney Spears' Greatest Throwback Photos The pair had "one of the world's biggest breakups" - according to Britney Spears herself - nearly 20 years ago, but that doesn't mean we can't reminisce on some of their greatest throwbacks By Andrea Wurzburger Published on April 16, 2020 03:39 PM Share Tweet Pin Email Trending Videos 01 of 14 Working for the Mouse Everett In 1993, Britney Spears and Justin Timberlake (along with Christina Aguilera and Ryan Gosling) joined The Mickey Mouse Club, though it wouldn't be until seven years later that they'd start dating. 02 of 14 Red Carpet Couple Jeff Kravitz/FilmMagic Justin interviewed Britney on the red carpet at the 2000 Grammys. 03 of 14 Cozying Up Dave Hogan/Getty Timberlake's sweater was made of boyfriend material at the 2000 MTV Video Music Awards. 04 of 14 The Double Denim Seen 'Round the World Frank Trapper/Corbis/Getty An iconic image from an iconic couple, the pair wore these matching denim get-ups to the 2001 American Music Awards. 05 of 14 Play Ball Kevin Mazur/WireImage The pair had their nicknames for each other, Pinky and Stinky, put on the back of their basketball jerseys for the 3rd annual Challenge for the Children charity event put on by *NSYNC. 06 of 14 Sparkle and Shine Steve Granitz/WireImage Britney rocked an oh-so-2001 slip dress while Justin wore an also of the time sparkly, pin-striped suit for a night out in Beverly Hills. 07 of 14 Showing Support Britney Spears, Justin Timberlake. Richard Corkery/NY Daily News Archive via Getty In November 2001, Justin was on hand to support his girlfriend at the release of her latest album, Britney. 08 of 14 Power Couple SGranitz/WireImage The pair decided not to match at the 2002 American Music Awards, which was such a bummer. 09 of 14 To a T Kevin Mazur/WireImage Britney and Justin posed coolly at the MTV Icon Tribute to Janet Jackson. 10 of 14 Super Bowl Superstars Scott Gries/ImageDirect/ Getty Britney and Justin's band *NSYNC joined Aerosmith, Nelly and Mary J. Blige at the 2001 Super Bowl halftime show. 11 of 14 Live from New York! Mary Ellen Matthews/NBCU Photo Bank/NBCUniversal via Getty In February 2002, just a month before their split, the pair appeared on Saturday Night Live together. 12 of 14 Premiere Date Christina Radish/Redferns/Getty Justin was there to support Britney at the premiere of her 2002 movie Crossroads in Los Angeles. 13 of 14 New York Minute James Devaney/WireImage He also accompanied her to the film's premiere in New York City. 14 of 14 Suit and Tie Jim Smeal/Ron Galella Collection via Getty Before announcing their split in March 2002, the pair attended the Grammys in late February.