Suggestions by @niiiii

Tara Reid

as Angela Hayes in American Beauty (1999)

Annette Bening

as Sheryl Hoover in Little Miss Sunshine (1997)

Bryan Cranston

as Lester Burnham in American Beauty (1999)

Eric Christian Olsen

as Steve Stifler in American Pie, 2, Wedding, & Reunion (2009-2022)

Josh Hutcherson

as Jim Levenstein in American Pie, 2, Wedding, & Reunion (2009-2022)

Paul Dano

as Paul Finch in American Pie, 2, Wedding, & Reunion (2009-2022)

Paul Dano

as Adam Webber in Blast From the Past (2020s Cast)

Eddie Kaye Thomas

as Damian Leigh in Mean Girls (1999)

Eddie Kaye Thomas

as Dwayne Hoover in Little Miss Sunshine (1997)

Dakota Fanning

as Olive Hoover in Little Miss Sunshine (1997)

Rachael Leigh Cook

as Beth McIntyre in John Tucker Must Die (1996)

Jenny McCarthy

as Jeanine Stifler in American Pie, 2, Wedding, & Reunion (2009-2022)

Tara Reid

as Karen Smith in Mean Girls (1999)

Josh Hartnett

as Aaron Samuels in Mean Girls (1999)

Jason Biggs

as Jason in Mean Girls (1999)

Brandy Norwood

as Heather Montgomery in John Tucker Must Die (1996)

Brenda Song

as Summer in Clueless (2005)

Seth Rogen

as Melcher in Blast From the Past (2020s Cast)

Kal Penn

as Troy in Blast From the Past (2020s Cast)

Penn Badgley

as Troy in Blast From the Past (2020s Cast)