The Pick-up Artist 1987
"The Pick-Up Artist... has finally met his match."
Meet Jack Jericho, a charming New York City smooth-talker who thrives on his reputation as the ultimate womanizer. Everything changes when he crosses paths with Randy, the sharp-witted daughter of a compulsive gambler drowning in mob debt.
Director: James Toback
Cast
Molly Ringwald
Randy Jensen
Robert Downey Jr.
Jack Jericho
Dennis Hopper
Flash Jensen
Danny Aiello
Phil Harper
Harvey Keitel
Alonzo Scolara
Vanessa Williams
Rae, Girl with Dog
Mildred Dunnock
Nellie
Brian Hamill
Mike
Tamara Bruno
Karen
Angie Kempf
Jack's Student
Frequently Asked Questions
What is The Pick-up Artist (1987) about?
Jack Jericho, a self-proclaimed womanizer, meets his match in Randy, the quick-thinking daughter of a compulsive gambler. As he falls for her, he's drawn into a world of debt, danger, and redemption against the gritty backdrop of 1980s New York City. The film explores whether love can change a man—or if some habits are too deeply ingrained to break.
Who directed The Pick-up Artist?
The film was directed by James Toback, a filmmaker known for his sharp, dialogue-driven narratives blending romance, crime, and social commentary.
Who stars in The Pick-up Artist?
The lead roles are played by Molly Ringwald as Randy and Robert Downey Jr. as Jack Jericho, supported by Dennis Hopper, Danny Aiello, Harvey Keitel, and Vanessa Williams in scene-stealing turns.
Is The Pick-up Artist (1987) worth watching?
With a runtime of just 81 minutes, this underrated gem offers more than your average rom-com. Robert Downey Jr.'s magnetic performance and Molly Ringwald's sharp chemistry make it a standout of 1980s indie cinema. While not a blockbuster, its blend of wit, style, and moral complexity makes it a rewarding watch for fans of romantic dramas with bite.
How long is The Pick-up Artist?
The film runs for 81 minutes.
🎥 Trailer
About The Pick-up Artist (1987) — A sharp romance where charm meets danger on NYC streets
Meet Jack Jericho, a charming New York City smooth-talker who thrives on his reputation as the ultimate womanizer. Everything changes when he crosses paths with Randy, the sharp-witted daughter of a compulsive gambler drowning in mob debt. Their instant connection becomes a battle of wits and wills, forcing Jack to confront the emptiness of his own lifestyle. Directed with sharp, edgy energy by James Toback, *The Pick-up Artist (1987)* blends razor-sharp dialogue with a heady mix of romance, dark humor, and urban grit to create a story about love, redemption, and the unexpected consequences of playing the game too long.
Set against the neon glow of 1980s New York, the film balances slick, fast-talking banter with a darker undercurrent of danger and moral reckoning. Robert Downey Jr. shines in his breakout role as Jack, while Molly Ringwald delivers a standout performance as the independent-minded Randy. With supporting turns from Dennis Hopper and Harvey Keitel adding depth and menace, this cult classic captures the electric tension and moral ambiguity of a city—and a romance—that demands more than just style.
