14. Adam Duritz and Jennifer Aniston
Say what? Yeah, this may have been back in the late 1990s (you know, when The Counting Crows were actually relevant and popular,) but it looks like Jennifer Aniston was the sweetie pie to frontman Adam Duritz. Well, she may have never been his “official” girlfriend, but the actress and the singer definitely had something going on way back in the day. This is a relationship that sort of just fell by the wayside, and most people don’t even know about it anymore, especially once Jennifer got mixed up with Ben Affleck. And we all know how that Ben-Jen thing worked out. Anyway, Adam also got some action from another lovely lady of Hollywood: Courteney Cox, who starred in a Counting Crows music video in 1997. After appearing on the set with Adam, Courtney started to get cozy with the frontman, which was interesting considering she was good friends with Jen.
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