Suggestions by @chris83

Ralph Macchio

as Max Miller in 90210 (80's)

Jason Gedrick

as Max Miller in 90210 (80's)

Jon Cryer

as Max Miller in 90210 (80's)

Zach Galligan

as Max Miller in 90210 (80's)

Lindsey Buckingham

as Soundtrack Composer in Beastly (1986)

Laura Branigan

as Soundtrack Composer in Beastly (1986)

Loverboy

as Soundtrack Composer in Beastly (1986)

Kenny Loggins

as Soundtrack Composer in Beastly (1986)

Cheap Trick

as Soundtrack Composer in Beastly (1986)

Cary Elwes

as Kyle Kingson in Beastly (1986)

Allan Kayser

as Kyle Kingson in Beastly (1986)

Robert Brian Wilson

as Kyle Kingson in Beastly (1986)

Brad Pitt

as Kyle Kingson in Beastly (1986)

Grant Show

as Kyle Kingson in Beastly (1986)

William Zabka

as Kyle Kingson in Beastly (1986)

Woody Harrelson

as Kyle Kingson in Beastly (1986)

John Stockwell

as Kyle Kingson in Beastly (1986)

Maxwell Caulfield

as Kyle Kingson in Beastly (1986)

Emilio Estevez

as Kyle Kingson in Beastly (1986)

Christopher Atkins

as Kyle Kingson in Beastly (1986)