Jerry Maguire (1996)
At the end of the 80s, Tom Cruise finally proved to critics that he was more than just the teen film star-turned-action hero with his role as a traumatized war veteran in Born on the Fourth of July . Halfway through the 90s, Cruise was back on critics' radars, this time for a role that was quite opposite to Ron Kovic. In Jerry Maguire , Cruise plays a high-strung, commitment-phobe sports agent in search of real friendship and love after the loss of his job. While Cruise had appeared in comedies and romance movies before, Jerry Maguire is arguably the first real romantic comedy he starred in -- and it remains one of the best outings of his career.