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IMDb rating
5.9

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Cast & Crew

Justin Reardon
Director
Luke Wilson
As Samson
Philip Baker Hall
As Granddad
Beverly D'Angelo
As Lyle's Girlfriend
Anthony Mackie
As Bryan
Chris Evans
As Narrator
Aubrey Plaza
As Mallory

Frequently asked questions

What is Playing It Cool about? Toggle content

Playing It Cool is a romantic comedy about a cynical screenwriter who doesn't believe in love until he meets the woman of his dreams. Despite being engaged to someone else, he falls for her and tries to win her heart. With the help of his quirky friends, he embarks on a series of misadventures to convince her to choose him over her fiancé. Along the way, he learns that love isn't a rational thing, but a feeling that can't be ignored. Will he succeed in winning her heart, or will he learn to live his own story? Find out in this charming and hilarious romantic comedy.

Where can I stream Playing It Cool? Toggle content

You can stream Playing It Cool on: Hulu Amazon Store Fandango at Home Peacock Tubi

What movies are similar to Playing It Cool? Toggle content

Some movies that have similar genres and were produced around the same time as Playing It Cool include Love, Rosie, What Men Want, The Spectacular Now, The Lobster, Focus, Killers.

When was Playing It Cool released in theaters? Toggle content

Playing It Cool was released in theaters on May 8, 2015.