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Playing It Cool poster

Playing It Cool

2014·Movie·R·94 min·5.8(811)

Love... it's a balancing act

A young man meets and instantly falls in love with an engaged woman.

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Where to watch Playing It Cool in United States

Click a service to open Playing It Cool there. Availability last verified on June 20, 2026.

Where is Playing It Cool streaming around the world?

CountryStreaming onRent / Buy
United StatesHoopla, The Roku Channel, Fandango at Home Free, Tubi TVAmazon Video, Fandango At Home
United KingdomAmazon Prime Video, Icon Film Amazon Channel, Amazon Prime Video with Ads, Rakuten TVApple TV Store, Amazon Video, Google Play Movies
CanadaAmazon Prime Video, Amazon Prime Video with Ads, Hoopla, Tubi TVCosmoGo, Amazon Video
AustraliaNetflix, Stan, Netflix Standard with AdsApple TV Store, Amazon Video, Google Play Movies
GermanyAmazon Prime Video, Joyn Plus, Amazon Prime Video with AdsApple TV Store, Amazon Video, Google Play Movies
FranceAmazon Prime Video, Molotov TV, Amazon Prime Video with AdsCanal VOD, Orange VOD, Amazon Video
SpainAmazon Video
BrazilApple TV Store, Amazon Video, Google Play Movies
JapanAmazon Prime Video, Amazon Prime Video with AdsAmazon Video, Apple TV Store, Google Play Movies

About Playing It Cool

Playing It Cool is a 2014 English-language comedy and romance film directed by Justin Reardon. The cast is led by Chris Evans, Michelle Monaghan, Topher Grace. It has a runtime of 1h 34m. Viewers rate it 5.8/10 across 800 ratings. In United States, it is currently streaming on Hoopla, The Roku Channel, Fandango at Home Free.

Playing It Cool was produced by Wonderland Sound and Vision and Voltage Pictures and made in United States of America. It was released on September 26, 2014, and carries a R certification. At the box office it grossed around $1 million worldwide.

Director
Justin Reardon
Writers
Paul Vicknair, Chris Shafer
Release date
September 26, 2014
Original language
English
Age rating
R
Status
Released
Country
United States of America
Box office
$1 million
Production
Wonderland Sound and Vision, Voltage Pictures
#screenwriter#romcom#romance#love#friends#los angeles, california#lying#engaged#amused

Playing It Cool cast & crew

Playing It Cool was directed by Justin Reardon and written by Paul Vicknair and Chris Shafer.

The cast features Chris Evans as Narrator, Michelle Monaghan as Her, Topher Grace as Scott, Aubrey Plaza as Mallory, Luke Wilson as Samson, and Martin Starr as Lyle.

Behind the camera, the score was composed by Jake Monaco, cinematography is by Jeff Cutter, and it was produced by Chris Evans and Nicolas Chartier.

Is Playing It Cool worth watching?

Playing It Cool holds an audience score of 5.8/10 from 811 ratings, a more divisive comedy films.

At 1h 34m, it's an easy, time-light watch.

If you enjoy comedy and romance, Playing It Cool is worth a place on your watchlist.

How and where to watch Playing It Cool

In United States, you can stream Playing It Cool on Hoopla, The Roku Channel, Fandango at Home Free, and Tubi TV, or rent and buy it on Amazon Video and Fandango At Home. Click any service above to open it directly.

Streaming rights change country by country and month by month, so the options above reflect United States today — switch your country at the top of the where-to-watch section to see availability elsewhere.

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Cast of Playing It Cool

Chris Evans

Chris Evans

Narrator

Michelle Monaghan

Michelle Monaghan

Her

Topher Grace

Topher Grace

Scott

Aubrey Plaza

Aubrey Plaza

Mallory

Luke Wilson

Luke Wilson

Samson

Martin Starr

Martin Starr

Lyle

Anthony Mackie

Anthony Mackie

Bryan

Ioan Gruffudd

Ioan Gruffudd

Stuffy

Philip Baker Hall

Philip Baker Hall

Granddad

Patrick Warburton

Patrick Warburton

Dick

Ashley French

Ashley French

Ashley Tisdale

Matthew Morrison

Matthew Morrison

Matthew Morrison

Playing It Cool — FAQs

Where can I watch Playing It Cool in United States?

Playing It Cool is streaming on Hoopla, The Roku Channel, Fandango at Home Free, Tubi TV in United States.

Is Playing It Cool on Hoopla?

Yes — Playing It Cool is currently available on Hoopla in United States.

What language is Playing It Cool in?

Playing It Cool is originally in English. Subtitle and dub options vary by streaming service.

How long is Playing It Cool?

Playing It Cool runs 1 hours 34 minutes (94 minutes).

What is Playing It Cool rated?

Playing It Cool is rated R. It holds a 5.8/10 audience score from 811 ratings.

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Playing It Cool (2014) — where to watch online · SearchOTT