Most film enthusiasts will be familiar with the satisfaction of stumbling upon an older film, watching it, and finding an obscure hidden gem. The Pickup Artist, a 1987 drama by writer/director James Toback, is not that film.

Frankly speaking, it should be. It stars a young Robert Downey Jr and a post-John Hughes Molly Ringwald. Its supporting cast includes Dennis Hopper, Harvey Keitel, and Danny Aiello. A major part of the film focuses on problem gambling and loan sharks, material Toback covered brilliantly when he wrote The Gambler (1974). Instead of utilising these elements to create an engaging drama, Toback squanders them to make a actively unlikeable one. It turns out there is a good reason why nobody talks about The Pickup Artist today.

Find a bad movie, and nine times out of ten its core problem will be its script. In The Pickup Artist, Toback effectively tries to blend two storylines that do not easily intersect. In one, Robert Downey Jr plays a school teacher whose life revolves around picking up and having sex with as many women as possible. In the other, Molly Ringwald plays a museum tour guide whose alcoholic father has run into debt with the Mafia. The presence of one plot shorts out the other. It is all a mad jumble, and a weirdly short one at that. Usually I am the first to complain that a film is running too long, but at less than 80 minutes The Pickup Artist feels badly truncated and flimsy.

It also saddles Downey with a strangely repellent character – harassing and stalking women on the street is not the charming frivolity that Toback’s script suggests it is. Ringwald’s character shares a brief sexual tryst with him in a car before pointedly and repeatedly telling him to go away. In return he follows her into her work, returns with a spontaneous school group she is obliged to show around, follow her home, force his way into her apartment, and volunteers to find the money to pay her father’s debts. One senses Toback felt the entire chain of events is romantic and sexy. Instead it is repellent, and never even remotely convincing.

Weirdly Keitel, Aiello, and Hopper all seem to play variations of characters they have already played, only devoid of detail or distinctiveness. It is bizarre that all three consented to performing in something this weak. Did they each owe Toback money? Were they doing him a favour? Or was there – and this is my honest suspicion – a much longer version of this film that was made but then pared back so extensively that its bones were exposed?

It’s Ringwald that I feel sorry for. One can imagine why she was attracted to playing her character: an adult woman with sexual agency, standing in stark contrast to her famous teen roles. The Pickup Artist came out just a year after Pretty in Pink. Were it a better film it just might have been the transition to grown-up parts that Ringwald sorely needed.