Suggestions by @gavin53zane

Matthew Lillard

as It in It (Advanced Casting)

Edward Norton

as It in It (Advanced Casting)

Matthew Lillard

as Pennywise in Stephen King's It (Minseries)

Edward Norton

as Pennywise in Stephen King's It (Minseries)

Crispin Glover

as Pennywise in Stephen King's It (Minseries)

Crispin Glover

as Pennywise the Dancing Clown in IT ( Cary Fukunaga's version )

Edward Norton

as Pennywise the Dancing Clown in IT ( Cary Fukunaga's version )

Matthew Lillard

as Pennywise the Dancing Clown in IT ( Cary Fukunaga's version )

Matthew Lillard

as Pennywise the dancing crown in It (2010)

Doug Jones

as It in It (2007)

Edward Norton

as It in It (2007)

Matthew Lillard

as It in It (2007)

Doug Jones

as It in It (2007)

Crispin Glover

as It in It (2007)

Edward Norton

as It in It (2007)

Matthew Lillard

as It in It (2007)

Matthew Lillard

as Pennywise the Dancing Clown in Stephen King's IT (1980s)

Crispin Glover

as Pennywise the Dancing Clown in Stephen King's IT (1980s)

David Bowie

as Pennywise in Book accurate It cast

Gary Goldman

as Pennywise in Book accurate It cast