Inspired by the great Federico Fellini's 8 1/2 by way of Woody Allen, Jake Squared resembles the work of both men only if they had suffered a severe brain injury. Written and directed by Sundance Institute alum Howard Goldberg, he puts together a notable cast of indie favorites: Elias Koteas, Virginia Madsen, and Jennifer Jason Leigh, but for a film that wants desperate to wring comedy from the narcissism and neuroses of Hollywood filmmakers its neither funny or particularly insightful.
Koteas (it's hard to believe he was ever Casey Jones in TMNT) play struggling director Jake Klein, whose career has hit the skids so hard he's not putting together a half-assed film about his own life. Describing himself as a "hopeless romantic", the 50-year-old seems to be exploring his numerous romantic entanglements in an effort to understand why he's never been able to commit. He hires a hotter, younger guy (Mike Vogel ) to play himself, and he seems to be shooting the film from his house, in the backyard jaccuzzi, or from his kitchen. While the setup suggests Allen's scathing self-deprecating Stardust Memories, Jake Squared aims to be lighter and funnier, but is consistently hamstrung by terrible writing and a needlessly convoluted narrative.
For some reason that's never sufficiently explained, other versions of Jake begin appearing on set. There's his 17-year-old self who wanted to be a rock star; Jake at 30 arrives even though he still looks 50 (just putting a hat on his doesn't hide Koteas' age); and a supposedly wiser Jake aged 40 shows up; all of whom dispense advice on current Jake's love life. Strangely, Jake, his two kids, and the cast interact with them like its nothing, and the same goes for all of his ex-girlfriends who keep turning up on set.
While it's no surprise that women are going to get short shrift in a film about a movie director's past loves, the level to which these characters are underwritten is astonishing. Jennifer Jason Leigh plays his current fling, who he sees every few months and talks to mostly over the phone. Virginia Madsen is perhaps the most sorely misused as Jake's longtime best friend and most plausible choice to be "the one". But her character has so little definition that her one shining moment involves an interlude where recounts to the audience everything they've just experienced. Yes, the film is so confusing, written so poorly, that Goldberg feels the need to spell it all out. You can almost feel him apologizing for the state of the nonsensical mess he's created. Jane Seymour, still breathtaking and looking half her age, passes through as his first love. Meanwhile, quotes from great philosophers are literally flung across the screen (the characters can interact with the words, somehow), but they only serve to underscore that the script can't adequately get across whatever point Goldberg is wanting to make. Koteas has slickster charm to spare as Jake, but the character comes off as a womanizing douche more than anything else. It's hard to really care whether he finds love because he doesn't seem to deserve it.
Ostensibly a meta rom-com, Jake Squared has little humor, zero romance, and is so painfully unaware that it counts as one of the worst self-referential comedies ever. In fact, they could make a Fellini film about how bad it is.
