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At that time, Timberlake was no more than “that blonde guy with the cute curls” of NSYNC, while Fergie was just finding fame with girl group Wild Orchid.They had a very brief relationship, which explains why we missed it.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.
They met at a White House event, but the pair never made public their relationship when they were together.Their subsequent relationships—Timberlake dated Britney Spears before dating and marrying Jessica Biel while Fergie married Josh Duhamel—were not shrouded in secrecy.#5 Sheryl Crow and Owen Wilson The Grammy Award-winning singer has dated a number of famous men like Eric Clapton, Kid Rock, and Lance Armstrong, and we were all in the know about these couplings.It was in 2006 when Lachey was a part of 98 Degrees and Kim K. But things fizzled out between them right after the first date. #2 Naomi Campbell and Leonardo Di Caprio It is evident that Leonardo Di Caprio has a weakness for supermodels. They had a brief relationship before Di Caprio went on to date other supermodels, most notably Amber Valletta, Gisele Bündchen, and Bar Rafaeli.According to Lachey, Kim tipped off the paparazzi about their movie date, so when they emerged from the theater, they found themselves staring at hordes of reporters and flashing cameras. #1 Cher and Tom Cruise when Cher was at the height of her musical career and Cruise was just blooming into the Hollywood A-lister that he is today.