Cast and Crew of Playing It Cool

Playing It Cool

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

Main Cast of Playing It Cool

Chris Evans as Narrator

Chris Evans

Narrator
Christopher Robert Evans (born June 13, 1981) is an American actor. He began his career with roles in television...
Michelle Monaghan as Her

Michelle Monaghan

Her
Michelle Lynn Monaghan is an American actress. Her first notable roles were in episodes of Young Americans, and Law...
Topher Grace as Scott

Topher Grace

Scott
Christopher John "Topher" Grace (born July 12, 1978) is an American actor. He is best known for his portrayal of...

Secondary Cast of Playing It Cool

Aubrey Plaza as Mallory

Aubrey Plaza

Mallory
Luke Wilson as Samson

Luke Wilson

Samson
Martin Starr as Lyle

Martin Starr

Lyle
Anthony Mackie as Bryan

Anthony Mackie

Bryan
Ioan Gruffudd as Stuffy

Ioan Gruffudd

Stuffy
Philip Baker Hall as Granddad

Philip Baker Hall

Granddad
Patrick Warburton as Dick

Patrick Warburton

Dick
Ashley Tisdale as Ashley Tisdale

Ashley Tisdale

Ashley Tisdale
Matthew Morrison as Matthew Morrison

Matthew Morrison

Matthew Morrison
Jaeden Martell as 6 Year Old Me

Jaeden Martell

6 Year Old Me
Fabianne Therese as College Girl

Fabianne Therese

College Girl
Gerry Bednob as Cabbie / Gabriel

Gerry Bednob

Cabbie / Gabriel
Beverly D'Angelo as Lyle's Girlfriend

Beverly D'Angelo

Lyle's Girlfriend
Kyle Mooney as Other Dude

Kyle Mooney

Other Dude
Scott Evans as Blissful Boy

Scott Evans

Blissful Boy
Brenda Schmid as Blissful Girl

Brenda Schmid

Blissful Girl
Sarah Dumont as Cute Girl

Sarah Dumont

Cute Girl
Mikaela Hoover as Lacey

Mikaela Hoover

Lacey
Devon Ogden as Sadie

Devon Ogden

Sadie

Crew of Playing It Cool

Full backstage crew list →