Lyle Carter (JEFF BRIDGES) is a successful Kentucky-based horse breeder and trainer who seems to have it all. While his wife, Rosie (SHARON STONE), spends most of the time in bed, Lyle is a workaholic who's in the process of selling Simpatico, his Triple Crown winner that should fetch him several millions dollars.
Thus, when he receives an emergency call from his former childhood friend, Vinnie (NICK NOLTE), he isn't pleased. Although he's been taking care of the destitute boozer, Lyle is no longer close to the man. Yet, when Vinnie tells him that he's been arrested and that damaging information about a past indiscretion may come to light, Lyle boards the first plane and heads for Los Angeles.
There, Lyle discovers that Vinnie is still living in the past, repeatedly watching old home movies of Rosie and the two of them, particularly related to their big winnings at the track. Vinnie also tells him that a cashier at the local grocery, Cecilia (CATHERINE KEENER), had him arrested for stalking her, but upon meeting the woman, Lyle learns this isn't true.
He also discovers that Vinnie set him up, and is now traveling back to Kentucky in search of Rosie, his former girlfriend, as well as former racing commissioner Simms (ALBERT FINNEY), a man now living under an alias due to the trio previously ruining his life and career after he discovered them involved in a racing scam.
As Vinnie sets out to set matters straight and various flashbacks of Vinnie (SHAWN HATOSY), Rosie (KIMBERLY WILLIAMS) and Lyle (LIAM WAITE) provide facts detailing how they ended up in their current states, the three try to come to terms with their past indiscretions that have forever shaped and haunted them.