There is a lot about Playing Cool that makes me want to like it. The cast (both lead and supporting) is comprised almost entirely of actors I like a lot. The film has some nice ideas it is playing with. It has some clever visual moments.
But the pacing and the storytelling? That is where it falls flat. And it keeps it from being a movie I truly enjoyed.
That it is a cliched tale of a screenwriter (Chris Evans) who does not believe in love, but then meets that one amazing woman (Michelle Monaghan)…but she has a boyfriend (Ioan Gruffudd). He seeks the advice of his friends and family (well, his grandad, played by Phillip Baker Hall). These characters are fairly well designed. There is the gay best friend Scott (Topher Grace), obligatory art performer girl secretly in love with the lead (Aubrey Plaza), disillusioned married buddy (Luke Wilson) and Oddball Played by Martin Starr.
The film tries to attack these cliches, but rather ineffectively. And there are numerous attempts at big emotional beats. Yet, the film never really earns these. I did not get the draw between the leads, everything was a rough sketch.
What makes this painful is the film has terrific imagery. Whenever Evan’s screenwriter starts getting philosophical, the film gets interesting to watch. There is a terrific scene where the Screenwriter (Evan’s and Monaghan’s characters are simply credited as “Me” and “her”) starts mocking the notion of there being “someone for everyone”. He talks about how there are those people who are such social misfits, there is no way they could find someone…but he is surprised by how many of them do. The picture becomes more colorful and vibrant, except for Evans, who is now black and white. There is an animated sequence where Grandad tells the tale of how he pursued the woman he loved (an outlandish tale of swimming an ocean, riding wild horses and so on). Evans talks about how his heart has let him, and stands in the background chain smoking. And we see Evans off to the side, smoke billowing from every pore, like Humphrey Bogart. The movie is wonderfully expressive at times.
As a said, I like the cast. In a fun bit of casting, Anthony Mackie is Evan’s agent (kind of a business wing-man). The cast is well chosen for their roles…
But the movie takes so any shortcuts, it never earns the big emotional beats and revelations. “Me” realizing who he would spend the rest of his life on a boat with after reading his friend’s (Grace) favorite book? It feels empty…it should be this hopeful and uplifting moment, but the film skips so much it feels rushed…except it somehow manages to slow down to a crawl, especially when focused on Evans and Monaghan. The film is full of ideas, and some pretty lofty intentions. But it jumps past what it needs to invest in. There is no sense of a real life for these characters.
The writers have only two movies (both Chris Evans films) to their writing credit and this is Director Justin Reardon’s first full length feature. I see some genuine potential in all three, but this film is not a ideal final product.
The creative style and cast make me want to like this movie. The cliches and lack of depth make me disappointed that it does not live up to those things.