The Pick-up Artist (1987 film)

The Pick-up Artist (1987 film) is an American romantic comedy film written and directed by James Toback, starring Molly Ringwald and Robert Downey Jr. The film centers on Jack Jericho (Downey Jr.), a skilled but immature womanizer who falls for Randy Jensen (Ringwald), a woman resistant to his advances. Jack's pursuit of Randy becomes intertwined with her attempts to protect her father, Flash (Dennis Hopper), from his gambling debts and dangerous creditors.

The plot revolves around Jack's efforts to prove himself to Randy, initially through his typical pick-up artist tactics which are unsuccessful with her, and later through more sincere actions aimed at helping her with her family's problems. Flash's gambling addiction and the threats it generates form a significant subplot, driving Randy's actions and testing Jack's commitment. The film explores themes of love, redemption, and the consequences of irresponsible behavior.

Supporting cast members include Danny Aiello, Harvey Keitel, and Bob Gunton. The film features a soundtrack composed by Georges Delerue. While it received mixed reviews upon its release, with critics divided on its tone and execution, The Pick-up Artist remains a notable entry in both Downey Jr. and Ringwald's filmographies, representing a particular era of romantic comedies. It is also considered a film that attempts to explore and critique, albeit controversially, the concept of "pick-up artistry."