Deal of a Lifetime  (1999)

Theatrical Release Information:
Deal of a Lifetime

Just how far would you go for a date with the girl of your dreams? Henry (Michael Goorjian) is a socially inept high school student who is constantly mooning over Laurie (Shiri Appleby), the most beautiful girl in his class. Henry announces he'd do practically anything to be able to go out with Laurie -- which, of course, is the cue for Jerry (Kevin Pollack), Satan's earthbound representative, to pay Henry a visit. In exchange for his soul, Jerry provides Henry with wealth, popularity, and a new girlfriend, Laurie. But before long Henry learns there's a downside to having everything you ever wanted, and as his life starts to spin out of control, Henry decides he'd rather have his old life back -- but does the Devil have a refund or exchange policy? Deal Of A Lifetime also features Jennifer Rubin and Ron Glass. ~ Mark Deming, All Movie Guide