Suggestions by @lorog

Judah Lewis

as Spider-Man in Marvel's Spider-Man 3: Part II

Leonardo DiCaprio

as Rick Riker / Dragonfly in Superhero Movie (1998)

rodriguezjace

as Writer in Marvel's Spider-Man 3: Part I

Mahershala Ali

as Nick Fury in Marvel's Spider-Man 3: Part I

Sean Astin

as Ben Parker in Marvel's Spider-Man 3: Part I

Damian Lewis

as Dr. Curt Connors in Marvel's Spider-Man 3: Part I

Grant Gustin

as Ted Hoffman in Marvel's Spider-Man 3: Part I

Natalia Dyer

as Betty Brant in Marvel's Spider-Man 3: Part I

Joe Morton

as Robbie Robertson in Marvel's Spider-Man 3: Part I

Bruce Willis

as J. Jonah Jameson in Marvel's Spider-Man 3: Part I

Charles Melton

as Flash Thompson in Marvel's Spider-Man 3: Part I

Wyatt Russell

as Eddie Brock in Marvel's Spider-Man 3: Part I

Winona Ryder

as May Parker in Marvel's Spider-Man 3: Part I

Sadie Sink

as Mary Jane Watson in Marvel's Spider-Man 3: Part I

Ben Affleck

as Sandman in Marvel's Spider-Man 3: Part I

Tanner Buchanan

as Harry Osborn in Marvel's Spider-Man 3: Part I

Thomasin McKenzie

as Gwen Stacy in Marvel's Spider-Man 3: Part I

Michael Shannon

as Green Goblin in Marvel's Spider-Man 3: Part I

Judah Lewis

as Spider-Man in Marvel's Spider-Man 3: Part I

rodriguezjace

as Writer in Marvel's Captain America: The Civil War