Where to watch Playing It Cool in Canada
Playing It Cool is streaming on Amazon Prime Video and Amazon Prime Video with Ads in Canada, and available to rent or buy on CosmoGo and Amazon Video. Availability checked 29 May 2026.
About Playing It Cool
Playing It Cool is a 2014 movie in the Comedy and Romance genres, directed by Justin Reardon, starring Chris Evans, Michelle Monaghan and Topher Grace. It has a runtime of 1 hour 34 minutes. It holds an average rating of 5.8/10 from 811 viewers. Below you can see where to watch Playing It Cool in Canada — across streaming, rental and purchase options — along with the full cast, trailer and viewer reviews.
Playing It Cool trailer
Overview
A young man meets and instantly falls in love with an engaged woman.
Top cast
Chris Evans
Narrator
Michelle Monaghan
Her
Topher Grace
Scott
Aubrey Plaza
Mallory
Luke Wilson
Samson
Martin Starr
Lyle
Anthony Mackie
Bryan
Ioan Gruffudd
Stuffy
Philip Baker Hall
Granddad
Patrick Warburton
Dick
Ashley French
Ashley Tisdale
Matthew Morrison
Matthew Morrison
Jaeden Martell
6 Year Old Me
Fabianne Therese
College Girl
Gerry Bednob
Cabbie / Gabriel
Beverly D'Angelo
Lyle's Girlfriend
Kyle Mooney
Other Dude
Scott Evans
Blissful Boy
Brenda Schmid
Blissful Girl
Sarah Dumont
Cute Girl
Themes & keywords
Frequently asked questions
Where can I watch Playing It Cool in Canada?+
In Canada, you can stream Playing It Cool on Amazon Prime Video and Amazon Prime Video with Ads. It's also available to rent or buy on CosmoGo and Amazon Video.
Is Playing It Cool on Netflix?+
Playing It Cool is not on Netflix in Canada right now, but you can stream it on Amazon Prime Video and Amazon Prime Video with Ads.
How long is Playing It Cool?+
Playing It Cool has a runtime of 1 hour 34 minutes (94 minutes).
Who stars in Playing It Cool?+
Playing It Cool stars Chris Evans, Michelle Monaghan, Topher Grace, Aubrey Plaza and Luke Wilson.
When did Playing It Cool come out?+
Playing It Cool is a 2014 movie directed by Justin Reardon.
What genre is Playing It Cool?+
Playing It Cool is Comedy and Romance film.
Who directed Playing It Cool?+
Playing It Cool was directed by Justin Reardon.
User reviews
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