The Winner (2007)

Narrated by a 43-and-a-half-year-old, incredibly rich and successful man, "The Winner" looks back to when the man lost his innocence and finally stepped into the world -- at the tender age of 32. It's 1994, and Glen Abbott is still living with his parents. When Alison, the only girl he's ever kissed, moves back to town, Glen decides to make something of himself in order to impress her. It's not in vain, thankfully -- for this unlikely underdog will eventually transform from nervous under-achieverto the richest man in Buffalo in just a few years. At the moment, though, the only person Glen can truly relate to happens to be Alison's 13-year-old son, Josh; they're both going through "puberty." Parental guidance comes courtesy of Glenn's enabling mother Irene and supportive but usually angry dad Ron.