Suggestions by @kamsismith

Sean Connery

as 1960s in What Actors Could've Played Rick Blaine in Various Decades?

Greta Gerwig

as Writer in Birkin: Unwrapped

Sofia Coppola

as Director in Birkin: Unwrapped

Cary Grant

as 1950s in What Actors Could've Played Rick Blaine in Various Decades?

Clark Gable

as 1930s in What Actors Could've Played Rick Blaine in Various Decades?

Humphrey Bogart

as 1920s in What Actors Could've Played Rick Blaine in Various Decades?

Rudolph Valentino

as 1910s in What Actors Could've Played Rick Blaine in Various Decades?

John Hughes

as Writer in Home Alone (1980)

John Williams

as Composer in Home Alone (1980)

John Hughes

as Producer in Home Alone (1980)

Eddie Redmayne

as Andrew Birkin in Birkin: Unwrapped

Steven Spielberg

as Director in Home Alone (1980)

James Earl Jones

as Marley in Home Alone (1980)

Winona Ryder

as Megan McCallister in Home Alone (1980)

Molly Ringwald

as Linnie McCallister in Home Alone (1980)

Alicia Vikander

as Lou Doillon in Birkin: Unwrapped

Matthew Broderick

as Buzz McCallister in Home Alone (1980)

John Goodman

as Uncle Frank McCallister in Home Alone (1980)

John Candy

as Peter McCallister in Home Alone (1980)

Tom Hardy

as John Prendergast in Birkin: Unwrapped