Suggestions by @kipwalker

Kenneth Branagh

as Director in Clue

Ralph Fiennes

as Professor Plum in Clue

John Goodman

as Colonel Mustard in Clue

Kate Hudson

as Alice Newton in Beethoven

Alec Baldwin

as Miss Trunchbull in Matilda

Cate Blanchett

as Director in Pocahontas

Lucas Hedges

as Matt Damon in Robin

Jason Segel

as Bill Murray in Robin

Mike Mitchell

as Director in Matilda

Valentina Gordon

as Matilda Wormwood in Matilda

Donald Trump

as Miss Trunchbull in Matilda

Paul Giamatti

as Harry Wormwood in Matilda

Lisa Kudrow

as Zinnia Wormwood in Matilda

Amanda Seyfried

as Miss Jennifer Honey in Matilda

Charles Grodin

as Grandfather Edward Stratton II in Silver Spoons

Jared Leto

as Aaron Boone in Nightbreed

David O. Russell

as Director in Rain Man

Steve Carell

as Raymond Babbitt in Rain Man

Miles Teller

as Charlie Babbitt in Rain Man

Kelli Berglund

as Susanna in Rain Man