Jennifer Aniston – Horrible Bosses

Thanks to her iconic role as Rachel on the hit sitcom series Friends, Jennifer Aniston has enjoyed a long and successful career playing your typical rom-com lead. Aniston would shatter those expectations and show that she was more than daring enough to break the mold in the role of Dr. Julia Harris in the raunchy 2011 comedy Horrible Bosses. Aniston was far from being the sweet female lead she's typically played and was instead a sex-driven and overbearing dentist who would frequently harass her dental assistant employee Dale, played by the always affable Charlie Day. Although the male rape joke involving her character has not aged well in the decade since, Aniston's willingness to play a character so against her usual gigs won over more fans and she continued to experiment with roles in the following years.