Writer-director Cameron Crowe’s biggest box office success, Jerry Maguire is equal parts sports movie and Billy Wilder dramedy. Tom Cruise’s Jerry Maguire is a slick sports agent struggling with his rediscovered conscience in an industry devoid of one. His romance with his big-hearted secretary, Dorothy Boyd (Renee Zellweger, breaking through in a big way), and his relationship with Dorothy’s son, Ray (Jonathan Lipnicki), helped make the movie a crowd-pleasing hit. While Cruise delivers an all-timer performance, the movie’s real MVP is Cuba Gooding, Jr., who won a much-deserved Best Supporting Actor Oscar for his role as Arizona Cardinals wide receiver Rod Tidwell. With a chip on his shoulder almost as big as the deficit in his bank account, Rod is the only client Jerry has left—and Gooding invests this relationship with endless charisma and energy. The way Rod goes from “Show Me the Money!” greed to his tearful, humbling mastery of “the Qwan” by the end of the movie is arguably the film’s greatest achievement.