At first, we find a smug and fresh-faced Jack Jericho (Robert Downey Jr.) concealed by the steam that has collected on the mirror in front of him. He wipes it clean, admires his visage, and runs through his repertoire of pick-up phrases with such confidence I don’t even think he blinks. The movie establishes early on that Jack is a professional philanderer, a man so attuned to the deception of women that it comes as second nature. The guy uses semantics with care and grace, and though his intentions are hedonistic, he never is coy about it. He’s a one-note character, a “perfect” ’80s protagonist. He spends the first 20 minutes (by and large the films best moments) employing his magic on various women around New York City before the plot kicks in. This, unfortunately, is where Downey’s charm cannot compensate for the film’s major setbacks.

Per usual, Jack corrals an unassuming woman on his way home from his teaching job. Randy Jensen (Molly Ringwald, in usual top form), though stony on her exterior, takes Jack up on his offer and takes it about six and half steps further than expected. After their midday coital interlude, Randy buttons up her blouse and promptly leaves Jack’s rusty red Camaro. This comes a surprise to Jack, who has grown accustomed to acquiring the numbers of his victims. She couldn’t show any more ambivalence to him if she tried. Jack watches longingly as she walks away from him, a stare far different from the one that inaugurated the film. What a groaner.

Why did ’80s films always have to be about a player getting played? It’s about the most overused rom-com staple on the market, and though it generally works, here it seems so rushed. It’s expected, as the film runs a brisk 81 minutes, but how did Jack fall in love with a woman over the course of an afternoon romp? We never know, as the script fails to develop the characters past dress preference and gait.

We later discover that Randy’s steely attitude comes as a result of her father’s (Dennis Hopper) debt to the mob, a sum of money he cannot compile because of his constant drinking habit. Dennis Hopper looks bored on screen, stumbling around and reading his lines solely for the paycheck at the end of the week. He’s wasted in this film, literally.

Jack creepily follows Randy back to her home, and it is here he meets the vile mob boss Alonzo (Harvey Keitel, hamming it up). He promises the money to him in 24 hours, and she’s in disbelief towards the gesture. Though she refuses the offer, he insists on helping her throughout the situation. Exuberance is his trademark, no doubt, but Downey’s charmingly eclectic take on Jack becomes a caricature by the middle of the second act and thus loses all credibility. I altogether stopped caring for Jack, and thus didn’t care for Randy or her problem. Without tension, we lose attention.

Randy continues to avoid Jack, but to no avail. She travels to Atlantic City with her gambling textbooks in hand, and Jack (as well as Randy’s father and a curiously ambiguous character played by Danny Aiello) are hot on her tail. With the aid of Jack and his endless supply of craft, Randy attempts to win the cash her father owes to the mafia.

The film’s ending is peachy, and offers a few tender moments that show just how talented Downey can be when he shows a little restraint. I’m not trying to say that he’s bad, but he’s just trying a little too hard too often. Overall, The Pick-Up Artist is never funny enough when it should be and the mob scenes are too barren to cast any real threat on the characters. The film just feels empty, sustained only by Downey’s taxing but endearing performance.

Kyle Kogan is a film critic living in Chicago.

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