The Pick-up Artist

The Pick-up Artist is a 1987 American romantic comedy-drama film produced and distributed by 20th Century Fox, written and directed by James Toback, starring Molly Ringwald and Robert Downey Jr. in the lead roles. Plot Jack Jericho is a 21-year-old womanizer, who's constantly honing his craft. Driving around the city in a red convertible, he regularly jumps out and skillfully charms women wherever he goes. The principal at the school where he teaches reprimands him for hitting on students' mothers. Outside of a club Jack hits on Lulu, who's waiting in her mobster boyfriend Alonzo's convertible. When he comes up he threatens him, so Jack goes inside. Mobster Fernando insists he wants Randy, a young redhead in the bar who's getting noticed by many, including Jack. Lulu follows Randy into the restroom, trying to convince her to go out with Fernando. She refuses, and points out she shouldn't be doing his dirty work. Outside, Lulu argues with Alonzo, so he leaves her there. Jack sees, offers her a lift and later a cop interrupts them as they are necking.