Mark Harmon portrays the lead character Taylor Worth, a man who takes on a bet to make three women fall in love with him at the same time.
Madeleine Stowe plays Veronica Briskow, one of the three women that Taylor Worth tries to win over as part of the bet.
Lesley Ann Warren portrays Eleanor Larimore, another woman that Taylor Worth attempts to make fall for him in Worth Winning.
Maria Holvoe plays Erin Cooper, a character involved in the romantic entanglements caused by Taylor Worth's bet.
Mark Blum portrays Ned Braudy in the movie Worth Winning.
Andrea Martin plays Claire Braudy, a character involved in the comedic situations that arise from Taylor Worth's triple date bet.
Tony Longo plays Tarry Childs in Worth Winning.
Alan Blumenfeld portrays Howard Larimore in the film.
Devin Ratray plays Howard Larimore Jr., a character in Worth Winning.
David Brenner portrays the Celebrity Auctioneer in the movie.
Jon Korkes plays Sam in Worth Winning.
Brad Hall portrays the character Eric in the film Worth Winning.
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