With this rote but well-cast romantic comedy, writer-director James Toback began his long association with actor Robert Downey, Jr. The latter stars as Jack Jericho, a grade school teacher and smooth operator who zealously polishes his cliched pick-up lines in front of a mirror. Jack's come-ons even work on Randy Jensen (Molly Ringwald), a redheaded museum tour guide who dishes up a stream of retorts, matching Jack's verbal banter. After quickly trysting in the back of Jack's car, Randy flatly thanks him and walks off. Realizing that Randy is his soul mate, Jack gets his pal Phil (Danny Aiello) to find her. She's in Atlantic City, desperately trying to win $25,000 with her paycheck. Her father, Flash (Dennis Hopper), is an inveterate alcoholic who owes the money to a mobster, Alonzo (Harvey Keitel). Alonzo is willing to erase the debt if Randy will sleep with a South American kingpin, so she's trying to hit a jackpot that will get her and Flash off the hook. With a deadline of tomorrow, Jack sets out to get Randy's money and convince her that he's Mr. Right. The Pick-Up Artist was the final film appearance of actress Mildred Dunnock, who played Jack's grandmother.