Suggestions by @lorog

Charlie Cox

as Kingpin in Spider-Gwen (2022)

Timothée Chalamet

as Harry Osborn in Spider-Gwen (2022)

Tom Holland

as Peter Parker in Spider-Gwen (2022)

Meg Donnelly

as Spider-Gwen in Spider-Gwen (2022)

Tom Holland

as RodriguezJace in myCast: Titan War

rodriguezjace

as Writer in Galactic Eclipse

Marisa Tomei

as Aunt May in Spider-Man: The Sinister Six (2027)

Blair Underwood

as Jefferson Davis in Spider-Man: The Sinister Six (2027)

J.K. Simmons

as J. Jonah Jameson in Spider-Man: The Sinister Six (2027)

Mackenzie Davis

as Jean DeWolff in Spider-Man: The Sinister Six (2027)

Danny Glover

as Robbie Robertson in Spider-Man: The Sinister Six (2027)

Harrison Ford

as John Stacy in Spider-Man: The Sinister Six (2027)

David Thewlis

as The Lizard in Spider-Man: The Sinister Six (2027)

Bokeem Woodbine

as Shocker in Spider-Man: The Sinister Six (2027)

Abigail Cowen

as Carlie Cooper in Spider-Man: The Sinister Six (2027)

Justice Smith

as Randy Robertson in Spider-Man: The Sinister Six (2027)

Andrey Ivchenko

as Rhino in Spider-Man: The Sinister Six (2027)

Aaron Paul

as Electro in Spider-Man: The Sinister Six (2027)

Angourie Rice

as Betty Brant in Spider-Man: The Sinister Six (2027)

Jacob Elordi

as Eddie Brock in Spider-Man: The Sinister Six (2027)