High Quality Content by WIKIPEDIA articles! The Pick-up Artist is a 1987 American film written and directed by James Toback. This romantic comedy starred Molly Ringwald and Robert Downey Jr. It was rated PG-13 by the MPAA. Randy Jensen is a smart, independent tour guide who beats womanizer Jack Jericho at his own game. After a quick fling, her indifference only causes him to become smitten with her. Randy is too busy for romance, trying to keep her alcoholic gambler father, Flash Jensen, out of harm's way. Jack's persistence soon pays off when he offers to help rescue Randy's dad from the mob. Toback was born in New York City. His mother, Selma Judith (nee Levy), was a President of The League of Women Voters and a moderator of political debates on NBC. His father, Irwin Lionel Toback, was a stockbroker and former Vice-President of Dreyfus & Company. Toback graduated from The Fieldston School in 1963 and from Harvard College, magna cum laude, in 1966.