You Win

What is it about sassy gay men that make them so hard to write as on-screen characters? It might work if they're sidekicks to the protagonist (and therefore taken in small doses) as in Kissing Jessica Stein or Will & Grace. But if one is the leading man of a mediocre movie, you're often spending two hours with a wannabe-Wilde who very quickly seems brittle, forced, condescending and phony. It takes a very talented writer to make an him likeable and a very talented actor to let the wit roll off his tongue with panache.

Unfortunately, we have no such luck with Nathan, the leading man in writer/director Russell Brown's Race You to the Bottom. Brown seems to like the idea of writing a young, successful, unabashedly sexual man (scratch the above "gay" adjective and make that "bisexual"), but Nathan is also narcissistic, inconsiderate, rude and sexually inconsiderate. And if you're going to make him "sassy" or "witty" or whatever, then you better give him some good lines. That doesn't happen.

For a brief summary, Nathan (Cole Williams) and Maggie (Amber Benson) abandon their respective boyfriends to take a trip to Napa for an article he's working on for a travel magazine. As soon as they leave, they're making out! Sassy! I think we the audience are either supposed to be so shocked (rubbing our eyes in disbelief, "say wha...?) or cheering them on ("Yeah, you go, sexual rule-breakers!"). But all I could think was "Really? She's cheating on her supercute boyfriend with a greasy Clay Aiken clone wearing way too much eyeliner?"

Some people mistakenly believe that they have to "identify" with the protagonists in art. While I didn't mind that I couldn't identify with Nathan (he actually tells Maggie "the taste of another man on your lips makes me hot." Who talks like that? And...really?), I at least wanted to understand what was so attractive about him to Maggie. The movie offers few clues: He spontaneously dances in hotel rooms! He...um...likes to drink wine! He can get erections!

That last quality is apparently what gives him an edge over Maggie's devoted but pouty boyfriend, Milo. When her friend points out what a great guy Milo is, Maggie guiltlessly shrugs it off. Apparently, to her, it's perfectly okay to cheat on your long-term boyfriend if he can't get it up. And it's perfectly okay to do this with a man who has a boyfriend of his own. The movie's tagline is "Maybe their boyfriends should worry..." Yeah, about STDs.

It's too bad, because the movie could really have approached a unique situation. There aren't many films out there that deal with bisexuality as a legit sexual orientation or, at least, worth exploring as such. The fact that she deems Nathan a "70/30" kind of guy is perfectly fine with Maggie, and I know a lot of women in real life who wouldn't mind if their gorgeous gay best friends were 70/30s as well. And I'm sure relationships like this do exist, however underrepresented in film they may be. But Brown can't do his subject justice, and his dialogue bounces from unrealistic to overused clichés. When Maggie's friend explains Nathan's sexual preference with "bisexuality is just one stop on the road to gayville," I was expecting one of the Sex and the City girls to pop in with "that was my line!"

In fact, Nathan is just so gosh darn sexual that he basically whips it out in front of every attractive guy he comes across. (But not around attractive women besides Maggie. Hmmm, maybe he's more 95/5.) Or he encourages them to whip it out. When they visit some friends during their road trip to Napa, Nathan effortlessly seduces the hunky husband, Joe (Justin Hartley, the only man in this movie who doesn't have the skinny, hairless build of a 12-year-old). But as he gives Joe a hands-on workshop in new masturbation techniques, Mr. Overly-Sexed-Up Nathan spaces out and we cut to an utterly pointless flashback. (Focus, Nathan! Aren't Gen Y-ers overly-medicated on ADD pills?) By the time we're back to the present, Joe zips up and gives the most unconvincing "wow" in cinema history. Geez, this movie about sexual boundary-breaking can't even get handjobs right.

As they ascend the hills of their vineyard-hopping adventure, they become irritated and annoyed with each other - he at her clinginess and prudery, she at his pursuits of his 70% side. One review generously compared this to Who's Afraid of Virginia Wolf? for Generation Y (or whatever the hell we are), but I think that's a bit of an overstatement. They say such awful things to each other (especially Nathan) that you're not quite sure why you want to be around them anymore. You could argue that Nathan is intentionally turning Maggie off after she declared her love for him - to save her, to protect her, to break her heart now because it would be even crueler to lead her on - but that would mean Nathan would have to think of someone besides himself.

First Maggie tells him that his need to seduce everyone is due to his self-loathing, then she accuses him of only loving himself. Which is it? Just like Nathan, the movie tries to have it both ways, mistaking snark for charm. And like Nathan, Race You to the Bottom sorely lacks the latter.

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