Suggestions by @lorog

Thomasin McKenzie

as Gwen Stacy in Spider-Man: Power and Responsibility

Edgar Wright

as Director in Spider-Man: Power and Responsibility

Ethan Hawke

as The Green Goblin in The Friendly Neighborhood Spider-Man: Turning Point

Green Goblin (Norman Osborn)

as The Green Goblin in The Friendly Neighborhood Spider-Man: Turning Point

Spoiler

as The Green Goblin in The Friendly Neighborhood Spider-Man: Turning Point

Jenna Ortega

as Shadowcat in The Friendly Neighborhood Spider-Man: Turning Point

Gary Oldman

as Professor X in The Friendly Neighborhood Spider-Man: Turning Point

Ethan Hawke

as Norman Osborn in The Friendly Neighborhood Spider-Man: Turning Point

Jimmy Smits

as J. Jonah Jameson in The Friendly Neighborhood Spider-Man: Turning Point

Tyler Perry

as Robbie Robertson in The Friendly Neighborhood Spider-Man: Turning Point

Haley Lu Richardson

as Betty Brant in The Friendly Neighborhood Spider-Man: Turning Point

Joshua Bassett

as Flash Thompson in The Friendly Neighborhood Spider-Man: Turning Point

Domhnall Gleeson

as The Lizard in The Friendly Neighborhood Spider-Man: Turning Point

Oscar Isaac

as Matt Murdock in The Friendly Neighborhood Spider-Man: Turning Point

Viggo Mortensen

as George Stacy in The Friendly Neighborhood Spider-Man: Turning Point

Meg Donnelly

as Gwen Stacy in The Friendly Neighborhood Spider-Man: Turning Point

Linda Cardellini

as Aunt May in The Friendly Neighborhood Spider-Man: Turning Point

Wyatt Oleff

as Harry Osborn in The Friendly Neighborhood Spider-Man: Turning Point

Isabela Merced

as Mary Jane Watson in The Friendly Neighborhood Spider-Man: Turning Point

Milo Gibson

as Wolverine in The Friendly Neighborhood Spider-Man: Turning Point