Directed by:
Justin ReardonCinematography:
Jeff CutterCast:
Chris Evans, Michelle Monaghan, Aubrey Plaza, Ashley Tisdale, Patrick Warburton, Topher Grace, Martin Starr, Anthony Mackie, Luke Wilson, Jaeden Martell (more)Plots(1)
Playing it Cool is a fresh, quirky and weirdly relatable story about Me (Chris Evans), a young screenwriter disillusioned by love. He meets a breathtaking young woman, Her (Michelle Monaghan), at a charity dinner by pretending to be a philanthropist. Only one problem... she's engaged. With his agent (Anthony Mackie) chasing him for a screenplay about love and against the better advice of his best friend Scott (Topher Grace), our young hero enters into a platonic relationship to be able to keep seeing Her. (Transmission Films)
(more)Cast
![Chris Evans](http://image.pmgstatic.com/cache/resized/w88h116crop/files/images/creator/photos/166/522/166522538_102f8e.jpg)
Chris Evans
USA
Best movies:
Avengers: Infinity War (2018)
Avengers: Endgame (2019)
Deadpool & Wolverine (2024)
![Michelle Monaghan](http://image.pmgstatic.com/cache/resized/w88h116crop/files/images/creator/photos/163/696/163696637_ab77ab.png)
Michelle Monaghan
USA
Best movies:
The Bourne Supremacy (2004)
Gone, Baby, Gone (2007)
Constantine (2005)
![Aubrey Plaza](http://image.pmgstatic.com/cache/resized/w88h116crop/files/images/creator/photos/167/022/167022406_9692f9.jpg)
Aubrey Plaza
USA
Best movies:
Monsters University (2013)
Scott Pilgrim vs. the World (2010)
Ned Rifle (2014)
![Ashley Tisdale](http://image.pmgstatic.com/cache/resized/w88h116crop/files/images/creator/photos/164/116/164116136_ae3d06.jpg)
Ashley Tisdale
USA
Best movies:
Donnie Darko (2001)
Phineas and Ferb the Movie: Across the 2nd Dimension (2011) (TV movie)
A Bug's Life (1998)
![Patrick Warburton](http://image.pmgstatic.com/cache/resized/w88h116crop/files/images/creator/photos/162/055/162055459_49e385.jpg)
Patrick Warburton
USA
Best movies:
The Emperor's New Groove (2000)
Family Guy Presents: Stewie Griffin - The Untold Story (2005) (video compilation)
The Venture Bros.: Radiant Is the Blood of the Baboon Heart (2023)
![Topher Grace](http://image.pmgstatic.com/cache/resized/w88h116crop/files/images/creator/photos/000/272/272509_611696.jpg)
Topher Grace
USA
Best movies:
Interstellar (2014)
Ocean's Eleven (2001)
Traffic (2000)
![Martin Starr](http://image.pmgstatic.com/cache/resized/w88h116crop/files/images/creator/photos/162/680/162680773_690b81.png)
Martin Starr
USA
Best movies:
Spider-Man: No Way Home (2021)
Spider-Man: Far from Home (2019)
Hero (1992)
![Anthony Mackie](http://image.pmgstatic.com/cache/resized/w88h116crop/files/images/creator/photos/165/282/165282877_e03f9d.png)
Anthony Mackie
USA
Best movies:
Million Dollar Baby (2004)
Avengers: Infinity War (2018)
Avengers: Endgame (2019)
![Luke Wilson](http://image.pmgstatic.com/cache/resized/w88h116crop/files/images/creator/photos/165/128/165128103_ebe99f.jpg)
Luke Wilson
USA
Best movies:
3:10 to Yuma (2007)
Jackass: Number Two (2006)
Horizon: An American Saga - Chapter 1 (2024)
![Jaeden Martell](http://image.pmgstatic.com/cache/resized/w88h116crop/files/images/creator/photos/164/386/164386845_3c370e.jpg)
Jaeden Martell
USA
Best movies:
Knives Out (2019)
It (2017)
St. Vincent (2014)
![Philip Baker Hall](http://image.pmgstatic.com/cache/resized/w88h116crop/files/images/creator/photos/000/269/269375_410985.jpg)
Philip Baker Hall
USA
Best movies:
The Truman Show (1998)
The Rock (1996)
Enemy of the State (1998)
Fabianne Therese
Best movies:
Endless Love (2014)
John Dies at the End (2012)
Southbound (2015)
![Tony Cavalero](http://image.pmgstatic.com/cache/resized/w88h116crop/files/images/creator/photos/158/031/158031441_646b29.jpg)
Tony Cavalero
USA
Best movies:
The Dirt (2019)
When We First Met (2018)
The DUFF (2015)
![Ioan Gruffudd](http://image.pmgstatic.com/cache/resized/w88h116crop/files/images/creator/photos/162/848/162848582_3beead.png)
Ioan Gruffudd
UK
Best movies:
Warriors (1999) (TV movie)
Black Hawk Down (2001)
Hornblower: The Even Chance (1998) (TV movie)
![Shira Scott Astrof](http://image.pmgstatic.com/cache/resized/w88h116crop/files/images/creator/photos/159/400/159400698_1e0f1c.jpg)
Shira Scott Astrof
Best movies:
Half Brothers (2020)
Playing It Cool (2014)
Hollywoo (2011)
Henrietta Meire
Best movies:
Low Down (2014)
Playing It Cool (2014)
Hello Ladies: The Movie (2014) (TV movie)
Jaden Alexander
Best movies:
Blue Jasmine (2013)
Big Eyes (2014)
Big Sur (2013)
Abby Ryder Fortson
Best movies:
A Dog's Journey (2019)
Ant-Man (2015)
Ant-Man and the Wasp (2018)
![Kyle Mooney](http://image.pmgstatic.com/cache/resized/w88h116crop/files/images/creator/photos/161/390/161390210_563f4f.jpg)
Kyle Mooney
USA
Best movies:
Batman vs. Teenage Mutant Ninja Turtles (2019)
Brigsby Bear (2017)
Hello, My Name Is Doris (2015)
![Sarah Dumont](http://image.pmgstatic.com/cache/resized/w88h116crop/files/images/creator/photos/160/188/160188286_e5872f.jpg)
Sarah Dumont
USA
Best movies:
Scouts Guide to the Zombie Apocalypse (2015)
Don Jon (2013)
Bad Ass 2: Bad Asses (2014)