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The Pick-up Artist (1987)

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Storyline:
A womanizer meets his match when he falls for the daughter of a mobster.
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Lorraine Bracco as Carla
Danny Aiello as Phil Harper
Dennis Hopper as Flash Jensen
Harvey Keitel as Alonzo Scolara
Robert Downey Jr. as Jack Jericho (as Robert Downey)
Frederick Koehler as Richie
Molly Ringwald as Randy Jensen
Vanessa Williams as Rae, Girl with Dog
Victoria Jackson as Lulu
Mildred Dunnock as Nellie
Polly Draper as Pat, Jack's Colleague
Robert Towne as Stan
Angie Kempf as Jack's Student
Brian Hamill as Mike
Tamara Bruno as Karen
Full cast
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