Told from the point of view of a screenwriter (Chris Evans) who doesn’t believe in love anymore, Playing It Cool wants to be both hip and a screwball romantic comedy and never quite succeeds at being either – though it’s fun watching it try.
After a quick comparison between the effects love has on the brain (being the same as various narcotics), Playing It Cool opens with Me (as the screenwriter is credited) being talked into writing a rom-com so as to get a leg up on an action movie script the studio plans to do next. His agent, Bryan (Anthony Mackie), assures him that it will lead to six weeks in Malaysia with all sorts of sexual fringe benefits.
Me finds himself completely unable to write the rom-com despite having a coterie of close friends who all believe strongly in the concept (of love, not the movie).
His gay friend, Scott (Topher Grace) even leaves copies of his favorite book – Love in the Time of Cholera – in hopes that it will be picked up and change lives in the way it changed his. Scott has a crush on a video store clerk but they totally disagree on what constitutes romantic movie (for Scott it’s Ghost; for the video clerk, it’s Terminator), so not necessarily the guy to be advising Me on romance.
His female friend (with occasional benefits), Mallory (Aubrey Plaza), in the beginning stage of a relationship but isn’t the type of person to offer advice unless part of a group. His friend Lyle (Martin Starr) lives in van so his advice is usually ignorable. His friend Samson (Luke Wilson) is all about taking chances.
None of them are much help because he’s been damaged by his mother leaving him with his granddad (Philip Baker Hall) when he was ten. Now his heart has moved from his chest and, in the form of a black clad hipster in a too cool pork pie hat (think a seedier version of Justin Timberlake) who follow him around at a distance, chain smoking.
In an effort to feel what his friends tell him about being in love, he tries to picture himself in their stories – recreated in a montage that is one of the funniest bits in the movie from its sheer visual absurdity. Nothing seems to help his writing.
Then, at a charity fundraising party, Me meets Her (Michelle Monahan). Their senses of humor seem to be much the same – they prank people at the party then giggle about it together. They are just so at ease with each other that he starts to feel something he hasn’t felt before but (of course) it turns out she has a boyfriend – whom he dubs Stuffy (Ioan Gruffuff) after meeting him. So he tries to hang out with her as friends. We all know how that’s going to go.
Still, he starts going to all these charity fundraisers, spinning tales about how much he loves doing charity work and winds up with a fan, Hedge Funder (Patrick Warburton), whom we know will screw things up for him when he’s trying to be, for once, genuinely heartfelt.
Playing It Cool was written by Chris Shafer and Paul Vicknar and directed by Justin Reardon – all of whom were clearly trying to do something different. Throughout the movie, Me’s fantasies add color and a certain wackiness that’s meant to be endearing and kinda screwball, but ultimately intrude on the heart of the story – and screw with the pacing a bit too much.
On the other hand, we have a cast with so much talent that it’s fun to watch them work – even while there are all these distractions going on. It’s also fun to see some rom-com clichés get stood on their heads – in particular, the running through the airport scene (another genuinely funny bit).
The best thing about Playing It Cool, whatever its flaws, is that it’s writers and director were not afraid to take some big chances – and that they got a cast that’s comedy gold to go along with them. The result is a non-standard rom-com that has more good moments than bad and doesn’t actually play it cool.
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