Jennifer Aniston and Paul Rudd
Number of projects together: 3
Projects: The Object of My Affection (1998), Wanderlust (2012), Friends (1994-2004)
The comedic duo have played romantic leads in two films together (well, sorta), but at very different stages of their fictional character’s lives. In The Object of My Affection, Aniston played a social worker who develops romantic feelings for her gay best friend (sorry, Jen). And in Wanderlust, Aniston and Rudd played a married couple, looking to shake things up with their over-stressed city life routines. Rudd also played Phoebe’s (Lisa Kudrow) husband on Friends for 17 episodes.