8. 'Jerry Maguire' (1996)
"Show me the money!" Despite being a heartthrob and having an impeccable sense of comic timing, Cruise rarely did romantic comedies. (Does Risky Business count?) But he was the perfect choice for Cameron Crowe's comedy about a hot-shot sports agent who has a moment of conscience and gives up everything to start his own scrappy company — all the while falling for his assistant, a single mom played by a darling Renee Zelwegger. It's certainly one of the most quotable romcoms of all time, in part thanks to the power of the Cruise-Zelwegger chemistry and Oscar winner Cuba Gooding Jr.'s turn as a lovably boisterous young football star.