Suggestions by @queenofnewyork2003

Sierra Boggess

as Tatiana Slozhno in Spies Are Forever (Mid 2000s film)

John Barrowman

as Agent Curt Mega in Spies Are Forever (Mid 2000s film)

John Landis

as Director in Black Friday (80s-90s movie)

John Landis

as Director in The Guy Who Didn't Like Musicals (80s-90s movie)

Ben Vereen

as Frank Pricely in Black Friday (80s-90s movie)

Tracy Pollan

as Emma Perkins in Black Friday (80s-90s movie)

Michael J. Fox

as Paul Matthews in Black Friday (80s-90s movie)

Macaulay Culkin

as Tim Houston in Black Friday (80s-90s movie)

Nathan Lane

as Man In A Hurry in Black Friday (80s-90s movie)

Barry Bostwick

as General John MacNamara in Black Friday (80s-90s movie)

Dean Butler

as Ethan Green in Black Friday (80s-90s movie)

Sara Gilbert

as Hannah Foster in Black Friday (80s-90s movie)

Melanie Griffith

as Linda Monroe in Black Friday (80s-90s movie)

Melissa Gilbert

as Lex Foster in Black Friday (80s-90s movie)

Barry Bostwick

as General John MacNamara in The Guy Who Didn't Like Musicals (80s-90s movie)

David Ogden Stiers

as Mr. Davidson in The Guy Who Didn't Like Musicals (80s-90s movie)

Malcolm McDowell

as Sam in The Guy Who Didn't Like Musicals (80s-90s movie)

Megan Follows

as Zoey in The Guy Who Didn't Like Musicals (80s-90s movie)

Jennifer Connelly

as Deb in The Guy Who Didn't Like Musicals (80s-90s movie)

Meredith Baxter

as Nora in The Guy Who Didn't Like Musicals (80s-90s movie)