Suggestions by @jdeav

Andie MacDowell

as Maria Hill in Spider-Man

Idris Elba

as Nick Fury in Spider-Man

Hugh Jackman

as Eddie Brock in Spider-Man

Will Poulter

as Flash Thompson in Spider-Man

Jack Black

as Rhino in Spider-Man

Mark Hamill

as Doctor Octopus in Spider-Man

Dylan Bruce

as Uncle Ben in Spider-Man

David Harbour

as Kingpin in Spider-Man

Jake Gyllenhaal

as Harry Osborn in Spider-Man

Joaquin Phoenix

as Norman Osborn in Spider-Man

Will Smith

as Electro in Spider-Man

Michael Fassbender

as Mysterio in Spider-Man

Jeremy Ray Taylor

as Ned Leeds in Spider-Man

Brandon Routh

as Hydro-Man in Spider-Man

Michelle Pfeiffer

as Aunt May in Spider-Man

Hailee Steinfeld

as Mary Jane Watson in Spider-Man

Bill Hader

as Stanley "Stan" Uris in It Chapter Two (Similar Casting)

Jake Gyllenhaal

as Edward "Eddie" Kaspbrak in It Chapter Two (Similar Casting)

Jeremy Ray Taylor

as Benjamin "Ben" Hanscom: in It Chapter Two (Similar Casting)

Idris Elba

as Michael "Mike" Hanlon in It Chapter Two (Similar Casting)