With news this week that Justin Timberlake is returning to music as a film composer we figured it would be a good time to take a look a back at his alleged sexual history and see how he compares to the other legendary swordsmen we’ve chronicled.
We’ll let Fergie herself describe this relationship: “He was 16 and I was 23…It was before he got real heavy with Britney.” The date and age don’t match up with what she’s saying (in 1996 she was 21), but there’s still no denying JT had skills at an early age.
Britney Spears (1999-2002)
Britney and Justin met while working together on the New Mickey Mouse Club when they were just little kids. They were both still in their teens when they became a couple and dated during their simultaneous rise as massive teen idols.
Jenna Dewan (2002)
Bet you didn’t know that Jenna Dewan (now married to Channing Tatum) was a backup dancer for ‘N Sync? JT did.
Alyssa Milano (2002)
Milano and Timberlake dated briefly right around the time he came out with his first solo album Justified.
Staci Flood (2003)
Flood was a dancer in Timberlake’s music video for “Rock Your Body.” She was also a member of The Pussycat Dolls dance troupe for a couple of years. Coincidentally, both of these jobs occurred right around the time JT was nailing her.
Cameron Diaz (2003-2006 )
Justin settled down for an inexplicable three years with Diaz after the two met at the Nickelodeon Kids’ Choice Awards. They allegedly broke up because of the next woman on this list.
Scarlett Johansson (2006, 2007, 2011)
Scarlett was in Timberlake’s music video for “What Goes Around/Comes Around Interlude” and the tabloids wildly speculated that they were more than just friends. We’re buying it. Especially since he spent the night over at ScarJo’s apartment as recently as 2011.
Jessica Biel (2007 to 2011, 2012 to Present)
Timberlake and Biel have been together for several years now except for a couple of bumps in the road (noted below), but now they’re engaged and that film he’s composing music for? She’s in it.
Olivia Munn (2010)
Supposedly one of the reasons Biel and Justin briefly broke up was because he was chasing Olivia Munn (among others) and got busted. Thankfully all has been forgiven now.
Mila Kunis (2011)
JT and Mila were friendlier to one another in public than just about any platonic guy and girl friends have ever been while out promoting their movie Friends With Benefits so everyone assumed they were doing it. We will too.
Other less-substantiated alleged flings…
Ashley Olsen, Beyonce, Elisha Cuthbert, Janet Jackson, Olivia Wilde
Photo credit: YouTube/Screen Gems