Suggestions by @prithvirajbasu

Angelica Teach

as Madame Thenardier in Les Miserables (with Pirates of the Caribbean characters)

Lord Cutler Beckett

as Thenardier in Les Miserables (with Pirates of the Caribbean characters)

Smaug

as Davy Jones in Pirates of the Caribbean (if Fictional characters played them)

The Big Bad Wolf

as Davy Jones in Pirates of the Caribbean (if Fictional characters played them)

Big Bad Wolf (Shrek)

as Davy Jones in Pirates of the Caribbean (if Fictional characters played them)

Captain America (MCU)

as Will Turner in Pirates of the Caribbean (if Fictional characters played them)

Captain America (MCU)

as James Norrington in Pirates of the Caribbean (if Fictional characters played them)

Prince Charming Fortuna

as James Norrington in Pirates of the Caribbean (if Fictional characters played them)

The Sheriff of Nottingham

as Blackbeard in Pirates of the Caribbean (if Fictional characters played them)

Thor (Marvel Cinematic Universe)

as Hector Barbossa in Pirates of the Caribbean (if Fictional characters played them)

Thor (Marvel Cinematic Universe)

as James Norrington in Pirates of the Caribbean (if Fictional characters played them)

Gellert Grindelwald

as Blackbeard in Pirates of the Caribbean (if Fictional characters played them)

Charles Dance

as Alfred in Matt Reeves Batman Universe

John Cleese

as Alfred in Matt Reeves Batman Universe

Gandalf the White

as Hector Barbossa in Pirates of the Caribbean (if Fictional characters played them)

Gandalf the Grey

as Hector Barbossa in Pirates of the Caribbean (if Fictional characters played them)

Lord Cutler Beckett

as Hades in Clash of the Titans Duology (with Pirates of the Caribbean characters)

Armando Salazar

as Kronos in Clash of the Titans Duology (with Pirates of the Caribbean characters)

Makunga

as Lord Cutler Beckett in Pirates of the Caribbean (if Fictional characters played them)

Pitch Black

as Lord Cutler Beckett in Pirates of the Caribbean (if Fictional characters played them)