Suggestions by @lorog

Timothée Chalamet

as Harry Osborn in Spider-Man Unchained (2031)

Meg Donnelly

as Gwen Stacy in Spider-Man Unchained (2031)

Spoiler

as The Hobgoblin in Spider-Man Unchained (2031)

Tom Holland

as Spider-Man in Spider-Man Unchained (2031)

J.K. Simmons

as J. Jonah Jameson in Spider-Man Continues (2029)

Danny Glover

as Robbie Robertson in Spider-Man Continues (2029)

Mackenzie Davis

as Jean DeWolff in Spider-Man Continues (2029)

Kyle MacLachlan

as Don Manfredi in (Spider-Man)

Sam Worthington

as Herman Schultz in (Spider-Man)

Jared Harris

as Dr. Otto Octavius in (Spider-Man)

Michael Shannon

as Norman Osborn in (Spider-Man)

Nathan Lane

as Dr. Miles Warren in (Spider-Man)

Johnny Depp

as Dr. Michael Morbius in (Spider-Man)

Hugo Weaving

as Dr. Curtis Connors in (Spider-Man)

Campbell Scott

as Captain George Stacy in (Spider-Man)

Julianne Moore

as Anna Watson in (Spider-Man)

Sean Astin

as Benjamin Parker in (Spider-Man)

Winona Ryder

as May Parker in (Spider-Man)

Sadie Sink

as Mary Jane Watson in (Spider-Man)

Maximilian Acevedo

as Flash Thompson in (Spider-Man)