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There are some questions constantly asked in Hollywood that are as ageless as who created Stonehenge and what happened to the dinosaurs? While Natalie Portman is using her Harvard degree to answer, “Can best friends be sex friends?” and James Cameron is using his technology to finally put to rest the notion “What can go wrong diving in caves?”, one question has plagued the studios for the past decade: Can Jake Gyllenhaal open a film as a leading man? The answer: inconclusive.

Flexing his box office muscles (and real ones with Anne Hathaway in the skin-filled Love & Other Drugs), Jake has always dodged the bullet when it comes to a film flopping. While Prince of Persia, a movie that clearly rested on his shoulders, scrounged up an okay $90 million compared to its jaw-dropping $200 million production budget, excluding its massive advertising campaign (did they pay for the sand too at that price?), the film got an overseas bailout. Jake got his second leading chance later last year with the aforementioned Love & Other Drugs, which made an underwhelming $32 million (breaking even with its budget). However, a Golden Globe nomination saved him from total embarrassment.

Now, enough with the number crunching.

So, I had to wonder, when did this Jake Gyllenhaal Hollywood love obsession start? I traced it back to the 2001 comedy Bubble Boy. While he got his start as a leading man in 1999's October Sky, it was Bubble Boy where he was pushed front-and-center, testing him as an audience draw. I am a fan of Gyllenhaal’s work and decided to use the analysis of Bubble Boy to also serve as a way to try to solve this conundrum, since he is about the only good thing Bubble Boy produced.

Bubble Boy stars Gyllenhaal as Jimmy Livingston, a boy born without immunities, forced to live in a bubble, for even a single germ can kill him. Overly protected by his religious zealot of a mother (hilariously played by Swoosie Kurtz – the only compliment I can give this mess of a film. A fake xenophobic ransom letter is one of the few offensive jokes that actually generates chuckles) Jimmy experiences his first taste of life when the sexy but sweet Chloe (Marley Shelton in a thankless role that you’d expect to have seen Tara Reid or Heather Graham in at the time) moves in next door and befriends him. Developing a true crush on Chloe, Jimmy is heartbroken when he finds out she is getting married to her douchebag boyfriend, Mark (Dave Sheridan). Forming a bubble suit, Jimmy enters the world for the first time, racing to Niagara Falls to stop the wedding and profess his love to Chloe.

Along the way, the movie turns into a Looney Tunes adventure, having constant and random side skits involving circus freaks, bikers, an extremely stereotypical Indian who drives a curry and ice cream truck, as well as a religious cult led by Fabio – the first indicator that this film is so not with us anymore.

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