The Pick Up Artist is a bizarrely bad movie of the kind only James Toback seems capable of. This mess of a romantic comedy and a gangster movie attempts to be both conventional and unconventional. Toback’s thing has always been arthouse style talky existentialism with a healthy dose of New York. Watching him try to cram that unusual sensibility into a mainstream movie would be unwatchable were it not for Robert Downey Jr. and Molly Ringwald who, at the very least, remain likable even as they struggle against a director lost in his attempt to serve the commercial and the arty.
Jack Jericho is a pick up artist. He practices his terrible pick up lines in his bathroom mirror before he leaves to run the streets like a dog chasing every squirrel in his field of vision. That Jack plies his trade in the morning before he goes to work as a grade school gym teacher, odd, inexplicable choice of profession aside, makes his aims seem strange from the very beginning. Is Jack looking for dates or sex or both? Writer-Director Toback doesn’t seem to know or very much care.
The comedy for Toback is in Jack’s failing, silly attempts at meeting women. He seems fascinated by Downey chatting up chicks and dedicates much of the first portion of the movie to just listening to Jack try and stay in front of the various women he accosts on the street. In fact, the movie pretty much derails from the very beginning because Toback is more interested in the pick up lines and Downey’s charm than he is in setting up the ludicrous gangster story that is shoehorned into this 82 minute movie.
Ringwald is barely on screen until there is less than an hour left in the movie’s run time. She’s also flat and uninteresting as written by Toback as a dream girl with daddy issues. Ringwald struggles against the binds of the character but as written she is at best the example of why the film fails so spectacularly in tying Toback’s oddball qualities with the attempts at conventional romantic comedy. It doesn’t help that Toback has cribbed much of her character from Pretty in Pink for this role right down to the alcoholic, character actor dad, Dennis Hopper in for Harry Dean Stanton in this lineup, and even her name, Brandie, just two letters off from Pink’s Andie.
Toback seems to want to recall that much better film and then give us Ringwald having sex with Downey after just meeting him as a middle finger to the Middle American values that Ringwald had come to exemplify as John Hughes’ muse. It's a bad decision not because those values don't deserve mocking on occasion but because The Pick Up Artist isn't nearly as good as Pretty in Pink and the last thing a bad movie needs is the overwhelming memory of a far better movie.
The Pick Up Artist is a really tough sit, even at a measly 81 minute run time. The failed attempt by Toback to mainstream his style for a hit romantic comedy is a shambling mess of bad ideas going nowhere. Harvey Keitel, Dennis Hopper, and Danny Aiello may try to give the film a shine but they are no match for Toback’s failed attempt at making his unconventional style match with the kind of movie that people actually buy tickets to see.
Toback is not a bad satirist. He may be something of a chauvinist, a rather obvious sexist but he does push some boundaries. His next time behind the camera with Robert Downey Jr. was 1997’s Two Girls and a Guy which I very much enjoyed. That film was the full Toback with no attempts at mainstreaming his style or taming his wild dialogue. In that film the point wasn’t a plot but a heady, flirty at times dangerous conversation.
As opposed to The Pick Up Artist which is the act of a bored filmmaker trying to adhere to the conventions of Hollywood and make a hit by copying and pasting elements of what he feels are lesser films while he indulges the little bits he actually enjoys, like the dumb pick up lines he seems to like more than any other aspect of this film. The rest of the film is a meaningless mash up of gangster cliches and exhausting romantic cliffhangers.
The Pick Up Artist is bad but it remains memorable because Robert Downey Jr. is now a major movie star and this is one of those embryonic performances where you can see that clear distillation of movie star charisma that is just waiting to burst out. Of course, before that happens he will have to crash and burn and fail and struggle and do interesting work while nearly killing himself before that assured stardom finally hits nearly 20 years later with the inception of the Marvel Universe.
It’s fascinating to watch Downey Jr. grow over time. The Pick Up Artist may not be the best example of that growth, as it is a quite terrible film but he’s not terrible in the movie that is quite a trick. Ringwald, who was a bigger star than Downey Jr. at the time of The Pick Up Artist doesn’t recover as well and 30 years later is barely seen on the big screen, especially compared to the ubiquity of her former co-star. For her, The Pick Up Artist engenders the first misstep of what will be several before her star fades almost completely.