Suggestions by @robertbarnes

Chevy Chase

as Seth Rogen in This is the End (1981)

Peter Sellers

as Christopher Mintz-Plasse in This is the End (1970s)

Jonah Hill

as Monkey Photographer in Zoolander (2011)

Jason Segel

as Luke Zoolander in Zoolander (2011)

Danny McBride

as Jacobim Mugatu in Zoolander (2011)

Jay Baruchel

as David in The 40-Year-Old Virgin (2015)

Chris Rock

as Smart Tech Customer in The 40-Year-Old Virgin (1995)

Vince Vaughn

as Cal in The 40-Year-Old Virgin (1995)

Jared Leto

as James Franco in Knocked Up (1997)

Will Smith

as Club Doorman in Knocked Up (1997)

Zach Galifianakis

as Jonah in Knocked Up (1997)

Dax Shepard

as Jay in Knocked Up (1997)

Zach Braff

as Jay in Knocked Up (1997)

Justin Long

as Jay in Knocked Up (1997)

Vince Vaughn

as Ben Stone in Knocked Up (1997)

Chris Farley

as Seth in Superbad (1980s)

Adam Sandler

as Officer Michaels in Superbad (1980s)

Wayne Knight

as Officer Michaels in Superbad (1980s)

Vince Vaughn

as Officer Michaels in Superbad (1997)

Jason Biggs

as Fogell in Superbad (1997)