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Lily works for a bookie, placing bets to change the odds at the track. When her son is hospitalized after an unsuccessful con job and resultant beating, she finds that even an absentee parent has feelings for her child. This causes her own job to go wrong as well. Each of them faces the down side of the grift.
In Los Angeles, the smalltime crook Roy Dillon is hit by a baseball bat in the stomach when he tries to swindle a bar attendant. His mother Lilly Dillon works in La Jolla for the powerful bookmaker Bobo Justus, who owns the Justus Amusement Company in Baltimore, placing bets to change the odds at the track but also stealing some money for her that she stashes in her Cadillac. When Lilly comes to Los Angeles to a horse race, she pays a visit to Roy after eight years without seeing each other, and she finds that he has an internal hemorrhage and sends him to the hospital, saving his life. When the experienced Lilly sees Roys girlfriend, the slut and con artist Myra Langtry, she immediately finds that Myra is a roper. But the grieved Roy does not pay attention to his absent mother and decides to travel with Myra to La Jolla to spend a couple of days resting. Myra sooner finds that Roy lives of short-con grift and proposes him a great plan to rope tycoons; further she unravels Lillys scheme with Bobos money. When Roy turns Myra and her offer down, the greedy women set in motion a betrayal that brings tragic consequences to each player.
Anjelica Huston
Lilly Dillon
John Cusack
Roy Dillon
Annette Bening
Myra Langtry
Jan Munroe
Guy at Bar
Robert Weems
Racetrack Announcer
Stephen Tobolowsky
Jeweler
Jimmy Noonan
Bartender
Richard Holden
Cop
Henry Jones
Simms
Michael Laskin
Irv
Eddie Jones
Mintz
Sandy Baron
Doctor
Lou Hancock
Nurse
Gailard Sartain
Joe
Noelle Harling
Nurse Carol Flynn
Ivette Soler
Maid
Pat Hingle
Bobo Justus
Paul Adelstein
Sailor - Young Paul
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