Kevin Kline quoting Napoleon (who I'm not sure actually ever said that) in Shari Springer Berman and Robert Pulcini's joint directorial effort, The Extra Man, gives us unintentionally good advice about how to watch this film. Like every other seemingly "original" movie you see a trailer for, The Extra Man is derived from a novel of the same name. Jonathan Ames, who penned the book, also helped Springer Berman and Pulcini write the script. Somehow though, I have a feeling the book is better.
Henry Harrison (Kevin Kline) may appear the central character of the movie, another misleading element in the trailer, but it all comes down to the alienation of Louis Ives, played by the evermore loveable Paul Dano (he puts Michael Cera's portrayal of awkwardness to shame). This alienation manifests itself early in the plot when Louis' sexual issues are made apparent from the get-go. After discussing The Great Gatsby with a student (suspend your disbelief at the thought of Dano being old enough to carry off the professorial role), he retreats to the teacher's lounge, where he can't resist grabbing a bra out of someone's bag and putting it on over his suit. Naturally, his boss walks in during this nod to Jean-Paul Gaultier's vision of fashion, subsequently contributing to his sacking. While Louis may not have a plucky, seize the day attitude, he ultimately takes this as an omen to finally move to Manhattan like he has always dreamed of doing.
Like every fresh off the boat Manhattanite, Louis makes a rather unfortunate choice about his living situation, being somewhat pressured to move in with Harrison after looking at the apartment earlier that day. Harrison is more than eager to take Louis on as a lodger (for a paltry 350 dollars a month no less. On East 91st Street. Yeah fucking right. You can't even get that price in Washington Heights). Harrison's motives are not all that sentimental, however, when he reveals to Louis that he's the best candidate because he's the only one that came to see the apartment who speaks English.
Louis is able to fill in the next piece of the survival puzzle by finding a job at an environmental magazine called Terra, where he meets the weird/somewhat annoying Mary Powell (Katie Holmes. See, Tom Cruise lets her work). At first, he is taken with her, in spite of the fact that she openly says she loves Bob Marley and has plans to go to Jamaica with her boyfriend. His faith in her confidence is so great that he even feels brash enough to confess to her that he sometimes pretends he's a character in an F. Scott Fitzgeraldesque novel with a narrator recounting his every move and thought. And it is at this point that we start to see Louis' craziness become more evident. Soon after, he goes to a prostitute (played by Patti D'Arbanville, who some may recognize as Rayanne Graff's drunken mother on My So-Called Life) to cross-dress and get spanked. Having gotten a small taste of sexual deviancy, Louis also goes to Sally's Tranny Bar, not because he's particularly interested in fucking, but because he wants to look like one of them.
As you might have gathered by now, The Extra Man is unequivocal in its absurd hilarity, but, at its core, I don't think the film has any idea what it is trying to express. And this is the fatal flaw that holds it back from being as good as it could be.