Courteney Cox in The Runner (1999)

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Ron Eldard is a gambling addict—the boy is always at it. He's dug himself deep into a hole, and he tries to get out of it by becoming The Runner (1999). Uncle Joe Mantegna tries to help him climb out of debt by getting him a gig running numbers for Deepthroat, a sadistic mobster played with evil glee by John Goodman. Ron isn't allowed to do any gambling himself, and John puts Ron through hell by testing him at every turn, sending him out to place bets with bookies and waiting for the moment his new servant slips up. That moment comes when Ron decides to buy a fancy rock for girlfriend Courteney Cox, and who can blame him? One look at Courtney having a ball in bed or strutting her stuff in a tight red top and any man would cross his boss.