Suggestions by @paulcoolman2

Dylan O'Brien

as Frank T.J. Mackey in Magnolia (2029)

Oscar Isaac

as Bruce Wayne [George Clooney] in The Burton Batman Quarter [2009-2017]

Brad Pitt

as Jerry Maguire in Jerry Maguire (1996)

Orson Welles

as Lancaster Dodd in The Master (1962)

Ryan Gosling

as Lieutenant Aldo "the Apache" Raine in Inglourious Basterds (2025)

Hailee Steinfeld

as Penny Benjamin in Top Gun (2006-2042)

Robert Redford

as Sebastian "Seb" Wilder in La La Land (1966)

Chris Pine

as Michael Sullivan in Road to Perdition (2025)

Demi Moore

as Mary in Sinners (90's)

Matthew McConaughey

as Argylle in Argylle (2010s)

Tom Cruise

as Producer in Risky Business (2013)

Kavinsky

as Composer in Risky Business (2013)

Will Gluck

as Director in Risky Business (2013)

Curtis Armstrong

as Mr. Rutherford in Risky Business (2013)

Dermot Mulroney

as Mr. Goodsen in Risky Business (2013)

Rebecca De Mornay

as Mrs. Goodsen in Risky Business (2013)

Jon Bass

as Miles Dalby in Risky Business (2013)

Tony Revolori

as Barry in Risky Business (2013)

Vincent Piazza

as Guido in Risky Business (2013)

Kelly Rohrbach

as Lana in Risky Business (2013)