Chuck and Buck (2000)

Two friends, inseparable in their youth, have grown up to be complete opposites. Charlie Sitter (aka Chuck) is living the American Dream. A fast-rising executive in the music business, he's not yet thirty but, ambitious, confident, and handsome. Chuck has already acquired all the trappings of success -- a gorgeous home in the Hollywood Hills, a fancy sportscar and a beautiful fiancee. Buck O'Brien's life couldn't be more different. Buck never went to college, he's never even had a job. What's more, he still lives at home with his mother. Refusing to grow up, Buck has remained a child at heart who watches TV, sucks on lollipops, plays with his Matchbox cars and listens to his old albums over and over. When Chuck and Buck are reunited following the death of Buck's mother, their disparate worlds collide and their friendship quickly disintegrates into a battle of wills. By the end of the film, both men are forced to come to terms with each other and with the dark secrets of their past.