
Playing It Cool (2014) | Streaming Guide & Showtimes
Playing It Cool (2014) — A young man meets and instantly falls in love with an engaged woman. Streaming on Amazon Video, Fandango At Home.
Playing It Cool (2014) Storyline
A young man meets and instantly falls in love with an engaged woman.
Full Cast & Crew
- Chris Evans as Narrator
- Michelle Monaghan as Her
- Topher Grace as Scott
- Aubrey Plaza as Mallory
- Luke Wilson as Samson
- Martin Starr as Lyle
- Anthony Mackie as Bryan
- Ioan Gruffudd as Stuffy
- Philip Baker Hall as Granddad
- Patrick Warburton as Dick
- Ashley French as Ashley Tisdale
- Matthew Morrison as Matthew Morrison
- Jaeden Martell as 6 Year Old Me
- Fabianne Therese as College Girl
- Gerry Bednob as Cabbie / Gabriel
Why Watch Playing It Cool?
The Vibe: Playing It Cool is a lighthearted, hilarious, and uplifting comedy movie that firmly establishes itself as a must-watch from 2014. The pacing and atmosphere are perfectly calibrated to keep you engaged from start to finish.
Fan Reception: While holding a polarized score of 5.9/10, it retains a dedicated audience who appreciate its specific stylistic choices and unique premise.
Who Should Watch It: Highly recommended for those looking for a fun, stress-relieving watch. If you enjoy character-driven arcs layered with comedy-specific tropes, this deserves a spot on your watchlist.
Movie Details & Production
Explore More
Discover where to watch Playing It Cool and thousands of other titles on Watchlist Wizard. We analyze streaming availability across 50+ platforms including Netflix, Hulu, Disney+, and HBO Max to help you find your next favorite movie.