Playing It Cool

Philip Baker Hall

Granddad

Ioan Gruffudd

Stuffy

Topher Grace

Scott

Michelle Monaghan

Her

Scott Evans

Blissful Boy

Luke Wilson

Samson

Patrick Warburton

Dick

Anthony Mackie

Bryan

Chris Evans

Narrator

Aubrey Plaza

Mallory

Kyle Mooney

Other Dude

Jaeden Martell

6 Year Old Me

Beverly D'Angelo

Lyle's Girlfriend

Gerry Bednob

Cabbie / Gabriel

Jasmine Marie Alhambra

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Rod Smith

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Casey Mako

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Fabianne Therese

College Girl

Martin Starr

Lyle

Ashley French

Ashley Tisdale

Mikaela Hoover

Lacey

Matthew Morrison

Matthew Morrison

Sarah Dumont

Cute Girl

Brenda Schmid

Blissful Girl

Devon Ogden

Sadie

Justin Reardon

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Liz Trainor

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