Suggestions by @chris83

Peter Coyote

as Phil Graham in Off Campus (80s)

Kevin Dobson

as Phil Graham in Off Campus (80s)

Martin Sheen

as Phil Graham in Off Campus (80s)

Miguel A. Núñez Jr.

as John Tucker in Off Campus (80s)

Kristoff St. John

as John Tucker in Off Campus (80s)

Chris Rock

as John Tucker in Off Campus (80s)

Forest Whitaker

as John Tucker in Off Campus (80s)

Larry B. Scott

as John Tucker in Off Campus (80s)

Eddie Murphy

as John Tucker in Off Campus (80s)

Laurence Fishburne

as John Tucker in Off Campus (80s)

Blair Underwood

as John Tucker in Off Campus (80s)

Kadeem Hardison

as John Tucker in Off Campus (80s)

'Til Tuesday

as Soundtrack Composer in Off Campus (80s)

Aerosmith

as Soundtrack Composer in Off Campus (80s)

Stan Bush

as Soundtrack Composer in Off Campus (80s)

Lindsey Buckingham

as Soundtrack Composer in Off Campus (80s)

Bonnie Tyler

as Soundtrack Composer in Off Campus (80s)

Chicago

as Soundtrack Composer in Off Campus (80s)

Kenny Loggins

as Soundtrack Composer in Off Campus (80s)

Franco Zeffirelli

as Director in Off Campus (80s)