Suggestions by @fredericarrowsmith
59,073 suggestions

Marty Feldman
as 1970s in What Actors Could've Played Pennywise in Various Decades?

Jerry Lewis
as 1940s in What Actors Could've Played Pennywise in Various Decades?

Buster Keaton
as 1920s in What Actors Could've Played Pennywise in Various Decades?

Charlie Chaplin
as 1920s in What Actors Could've Played Pennywise in Various Decades?

Macaulay Culkin
as 2000s in What Actors Could've Played Pennywise in Various Decades?

Robert De Niro
as 1970s in What Actors Could've Played Pennywise in Various Decades?

Michael Jackson
as 1980s in What Actors Could've Played Pennywise in Various Decades?

Vincent Price
as 1950s in What Actors Could've Played Pennywise in Various Decades?

Peter Cushing
as 1950s in What Actors Could've Played Pennywise in Various Decades?

Martin Landau
as 1960's in What Actors Could've Played Pennywise in Various Decades?

David Bowie
as 1970s in What Actors Could've Played Pennywise in Various Decades?

David Tennant
as 2010s in What Actors Could've Played Pennywise in Various Decades?

Gene Wilder
as 1970s in What Actors Could've Played Pennywise in Various Decades?

Christopher Walken
as 1980s in What Actors Could've Played Pennywise in Various Decades?

Robert Englund
as 1990s in What Actors Could've Played Pennywise in Various Decades?

Jared Leto
as 2010s in What Actors Could've Played Pennywise in Various Decades?

Austin Butler
as 2020s in What Actors Could've Played Pennywise in Various Decades?

Heath Ledger
as 2000s in What Actors Could've Played Pennywise in Various Decades?

Joaquin Phoenix
as 2000s in What Actors Could've Played Pennywise in Various Decades?

Andy Serkis
as 2000s in What Actors Could've Played Pennywise in Various Decades?