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"It was not intentional and is regrettable." Incidentally, when While Timberlake and actress Jessica Biel are happily married with a son, it's no secret that their road to the alter was filled with dramatic headlines, breakups and, perhaps worst of all, multiple allegations of cheating. Still, rumors of infidelity continued to plague their relationship.

Arguably the biggest allegation came in October 2010, when reported that Timberlake had engaged in a three-day fling with actress Olivia Munn after meeting her at an event for My Space. On the heels of their breakup in 2011, Timberlake's Timberlake and Biel's relationship continued to make awkward headlines even after they tied the knot.

It was the boob that shook the world: at the 2004 Super Bowl halftime show, legendary singer, dancer, and performer Janet Jackson took to the stage with JT.

Their halftime show was obviously going to be a sexy one—with these two, there's really no other choice—but things got way out of hand.

According to the new issue of Us Weekly, Timberlake, 30, and Johansson, 26, had an early morning rendezvous Sept. An eyewitness tells the magazine that the couple, who appeared in Timberlake's 2006 music video for "What Goes Around…

As one might expect, the video prompted a massive backlash online.

Timberlake was forced to kind-of-sort-of apologize for the clip's contents on his website.

To this day, one could argue that her career never recovered.

Timberlake, meanwhile, received little to no backlash at all.

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