I like James Toback because he's so full of shit, not despite it. With arty provocateurs like Toback and Von Trier much of the fun lies in separating truth from bullshit. Toback is a sex-and-gambling-crazed obsessive who's made a strange little career out of documenting the neuroses and angst of sex-and-gambling-crazed obsessives. More than anything I love James Toback's New York, a sprawling metropolis populated by millions of gorgeous women begging to be seduced. It's a city powered by the friction between hot-blooded men and women, a giant dance hall where the intricate tango of attraction and repulsion between the sexes is the main attraction and the soundtrack forever hearkens back to the orchestral teenage drama of Phil Spector's Wall Of Sound.
Toback's NYC is full of big talking self-styled intellectuals, thuggish brutes and tough dames far too knowledgeable about the thorny intersection of sex, money and power. In 1987's The Pick-Up Artist Robert Downey Jr plays one of the aforementioned big-talking self-styled intellectuals, a rapacious womanizer first seen auditioning a battery of interchangeable pick-up lines into the mirror like an actor diligently rehearsing a script.
On a primal level Downey Jr gets what Toback's all about. He intuitively understands the playful, badgering sexuality, shameless exhibitionism and verbal one-upmanship at the core of Toback's oeuvre. Maybe that's why Toback has reused him again and again. As The Pick-Up Artist opens Downey Jr is busy playing the percentages, hitting on every pretty woman he encounters out of the conviction that at least a few will fall for his ossified shtick. Then one day Downey Jr. meets Molly Ringwald, the tough-talking daughter of drunken, debt-plagued gambling addict Dennis Hopper.
Downey Jr. becomes obsessed with Ringwald and vows to help her and her family out of a jam with glowering mobster Harvey Keitel. For its first twenty minutes or so The Pick-Up Artist bops along happily, driven by an infectious retro soundtrack, smart location shooting and the buzzy charisma of Downey Jr. Then Ringwald arrives and the film dies a quick, painful death. In order for The Pick-Up Artist to work dramatically the audience needs to believe that Ringwald is such a luminous, irresistible siren that Downey Jr. would happily cast all other women aside and selflessly devote himself to rescuing Ringwald despite only knowing her for a day or two at most. That was probably easier to buy in 1987. After all American had fallen in love with Ringwald. Why wouldn't Downey Jr follow suit?