Final film where Robert Downey, Jr. was billed as simply "Robert Downey."
Robert Downey, Jr. has said of this movie at the "Robert Downey, Jr. Film Guide" website: "I thought The Pickup Artist (1987) would give me a chance to have a real career, and it didn't turn out that way. When I was shooting the film I was running and jumping and flipping out and (James) Toback would say, 'Okay, that was great. Let's try another. Take ninety!' The press kept asking me about legal and moral issues. I'm like, 'Come on, man, I just hope it does well at the box-office.' Of course it's a sexually irresponsible film, but if AIDS had happened six months later, maybe the film would have made more than six bucks. Everyone thought that film must have had heavy sex scenes that were cut. Molly (Ringwald) and I only kissed once in the movie. Well, actually, we kissed like 40 times for the one scene. That was because Warren Beatty was helping Toback. Beatty's really knowledgeable in a lot of areas, especially fucking. Especially kissing and making actors do something 40 times, Toback used a lot of humor to get the best from us. After a take, he might tell me, 'You suck,' and I could laugh and agree. We were doing a scene where Molly's character is walking away from me, and she drops a bottle of antacid. I have to pick it up before she can get it and say, 'God, is there something wrong with your stomach?' She has ulcers because of all the stuff going on with gambling. There's usually this understood thing between actors, that if something has to happen in a scene, we help each other make it happen. But while we were doing it, she dropped the bottle and I went to pick it up. But she picked it up before I did, and the scene was over. What she was saying was, 'Listen, if you're really going to be in the moment, you've got to get it before I can.' It was just a really ballsy thing to do. It was probably one of the more important lessons I learned, especially because it's so easy to be desensitized and wish to be in the station wagon going home."
First starring role of Robert Downey, Jr.
Molly Ringwald has said that Warren Beatty, who produced, played a huge part in shaping the film and her acting. She claims Beatty directed most of her scenes, and even allowed her to write one.
The movie was filmed during May, June, July, and August 1986.