Suggestions by @kylewhite

Harold Ramis

as Writer in Uncle Buck (1999)

Harold Ramis

as Director in Uncle Buck (1999)

Richard Kind

as Bob Russell in Uncle Buck (1999)

Bryan Cranston

as Bob Russell in Uncle Buck (1999)

Linda Cardellini

as Tia Russell in Uncle Buck (1999)

Bonnie Hunt

as Chanice Kobolowski in Uncle Buck (1999)

Dan Aykroyd

as Buck Russell in Uncle Buck (1999)

Roy Scheider

as Mr. Bucket in Willy Wonka and the Chcolate Factory (1981)

Charlie Day

as Sporting Goods Manager in Step Brothers (2018)

Laraine Newman

as Cousin Catherine in National Lampoon's Vacation (1993)

Joe Dante

as Director in Back to the Future (1995)

Neve Campbell

as Lorraine Baines in Back to the Future (1995)

Terry Crews

as Matheson in Happy Madison's Pineapple Express (2008)

Tom Hanks

as Dr. Emmett Brown in Back to the Future (1995)

Robert De Niro

as Dr. Emmett Brown in Back to the Future (1995)

Dan Aykroyd

as Dr. Emmett Brown in Back to the Future (1995)

Steve Martin

as Dr. Emmett Brown in Back to the Future (1995)

John Lithgow

as Dr. Emmett Brown in Back to the Future (1995)

Seth Green

as Marty McFly in Back to the Future (1995)

Rachelle Lefevre

as Angie Anderson in Happy Madison's Pineapple Express (2008)