Suggestions by @theaterteenager

Owen Wilson

as Jim McAllister in Election (2009)

Alyson Hannigan

as Diane McAllister in Election (2019)

Jonah Hill

as Mr. Wendell Hall in Clueless (2025)

Alexander Payne

as Director in Clueless (2015)

Mark Waters

as Director in Clueless (2015)

Patton Oswalt

as Mr. Wendell Hall in Clueless (2015)

Mark Waters

as Director in Clueless (2005)

Mark Waters

as Director in Mean Girls (2014)

Jonathan Levine

as Director in Mean Girls (2014)

Cameron Diaz

as Jo Metzler in Election (2019)

Patton Oswalt

as Joseph Silverman in Hail, Caesar! (2006)

Martin McDonagh

as Director in O Brother, Where Art Thou? (2010)

Joel Coen

as Director in O Brother, Where Art Thou? (2010)

Jennifer Aniston

as Penny Wharvey-McGill in O Brother, Where Art Thou? (2010)

Malcolm-Jamal Warner

as Tommy Johnson in O Brother, Where Art Thou? (2010)

James Marsden

as Delmar O'Donnell in O Brother, Where Art Thou? (2010)

Oscar Isaac

as Pete Hogwallop in O Brother, Where Art Thou? (2010)

Ben Affleck

as Ulysses Everett McGill in O Brother, Where Art Thou? (2010)

Cameron Boyce

as Paul Metzler in Election (2019)

Jenna Ortega

as Tammy Metzler in Election (2019)