A true cult classic of dark comedies, Office Space initially didn't find its audience when it first hit theaters in 1999. Soon after though, people everywhere found themselves relating to the struggles of its lead characters, as well as their desire to rebel against their managers. In the midst of these struggles, comes Peter's relationship with a waitress named Joanna, played by Jennifer Aniston. This is one of her most relatable, down-to-earth performances and a huge factor in the movie’s place in people’s hearts.
Anti-rom-com, The Break-Up, stars Aniston and Vince Vaughn as one-half of a disgruntled couple who decide to end things, only to continue living together in their Chicago condo. There are no meet-cutes in this film, only well-crafted frustrations. While this plot could've easily been a turnoff, Aniston and Vaughn, who reportedly actually became a couple after filming The Break-Up, strike the right balance, selling the hardships of their separation in amusing ways.
Nothing was more surprising than seeing Aniston as a filthy-mouthed dentist who delights in sexually harassing her assistant, in the 2011 comedy “Horrible Bosses.” Playing alongside Jason Bateman, Jason Sudeikis, and Charlie Day, Aniston truly leans into her comedy skills, in a role that made waves for being a ‘departure’ from her usual gig.