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. (credited on-screen as Robert Downey) in the lead roles.

Mobster Fernando insists he wants Randy, a young redhead in the bar who is getting noticed by many, including Jack.

Seeing Randy in the street, she surprises Jack by agreeing to have a quick fling in his car but refuses to give him her number.

Randy is too busy for romance, trying to keep her alcoholic gambler father Flash Jensen, out of harm's way.

Randy is reminded about the offer to have the debt forgiven if she spends the evening with mobster Fernando, but she again refuses.

She starts up a conversation with fellow passenger Harriet, who talks about her long string of failed relationships.

Alonso was called in by the mobster running the casino, so he is also there and tries to block them from authorizing a large bet by Randy.

Although Jack has freed Randy and Flash of their debt and declares he wants them to be together forever, she insists they are bad for each other.

James Toback wrote the film for Warren Beatty who liked the script but was reluctant to play a character driven by his erotic compulsions.

Toback then considered Robert De Niro but ultimately decided the role should be played by a younger actor.

If you were casting Pick Up Artist 30 years ago you would have wanted Cary Grant and Irene Dunne.

[3][4][5][6] The film opened at number 5 at the US Box Office, and finished 85th for the year in 1987, with a $13.9 million domestic gross.