In 2009, Cooper and a list of hilarious co-stars, including Zach Galifianakis, Ken Jeong, and Heather Graham, would thrill audiences with the hit comedy, “The Hangover.”
The film was actually based on true events and was written by Jon Lucas and Scott Moore after they learned about their friend’s (and executive producer’s) friend who’d disappeared after a raunchy night at a strip club, leaving behind a large bill. It won the Golden Globe for Best Motion Picture in a Musical or Comedy.
Flings in Tinsel Town
Cooper has been spotted with a number of famous women throughout the years, including plenty of A-listers. One such woman is Cameron Diaz, who was seen with the actor acting very close, a number of times in 2007.
Of course, neither would cop to them hanging out being anything more than friendship. When the actor spoke to "People," he said, “I think she’s great. We’re good friends.” On one occasion, the pair was seen at a Giants-Eagles game with Ashton Kutcher and Demi Moore.
A New Romance
Though no one can be certain whether or not anything more than public hangouts occurred between Cooper and Cameron Diaz, the two being spotted together didn’t last for very long. It wasn’t long after, however, that he partnered up with talent agent and younger sister of "Fast and Furious" actress Jordana Brewster, Isabella Brewster.
A lot of the pair’s relationship was left to speculation, but they were together for about a year in 2008-2009 before Cooper moved on to another star.
The Rumor Mill
During the same time that Cooper was enjoying riding high from the success of "The Hangover," the rumor mill started to speculate that he was dating yet another star. The actor was rumored to have hooked up with "Wild Things" star Denise Richard in 2009 – but if you ask her, she’ll deny it.
In fact, she told one reporter that “it’s such bull[expletive].” The two were reportedly spotted out together in public a few times. But it wouldn’t be long before the press would move on to the next story.
Another One Bites the Dust
Once the actor had reached A-list status, the rumored romances with him and other stars just seemed to accumulate. And, in some cases, it was because the rumors were based in truth, and he was actually hooking up with them, but other times, it was just that – rumors (which are still flying around the internet rampantly today!)
According to Cooper, that’s exactly what happened with his "He’s Just Not That into You" co-star, Jennifer Aniston. Reports stated that they dated briefly in 2009, but he later cleared it up and revealed they were only ever friends.