Suggestions by @milesyeargain

Jean-Claude Van Damme

as Task Master in Hawkeye and Black Widow: Double Target (1988)

Geena Davis

as Black Widow in Hawkeye and Black Widow: Double Target (1988)

Kevin Costner

as Hawkeye in Hawkeye and Black Widow: Double Target (1988)

Mel Gibson (Wolverine)

as James “Logan” Howlett in Captain America: Liberty and Justice (1988)

Samuel L. Jackson

as Gabe Jones in Captain America: Liberty and Justice (1988)

John Ashton

as Dum Dum Dugan in Captain America: Liberty and Justice (1988)

Alec Baldwin (Young)

as Sgt. Nick Fury in Captain America: Liberty and Justice (1988)

Charlie Sheen

as Bucky Barnes in Captain America: Liberty and Justice (1988)

Helena Bohnam Carter

as Peggy Carter in Captain America: Liberty and Justice (1988)

Alan Rickman

as Red Skull in Captain America: Liberty and Justice (1988)

Brad Pitt (Captain America)

as Captain America in Captain America: Liberty and Justice (1988)

Alec Baldwin (Young)

as Colonel Nick Fury in The Invincible Iron Man: Rise of The Mandarin (1988)

Ernie Hudson

as War Machine in The Invincible Iron Man: Rise of The Mandarin (1988)

Kim Basinger

as Pepper Potts in The Invincible Iron Man: Rise of The Mandarin (1988)

Jack Palance

as Justin Hammer in The Invincible Iron Man: Rise of The Mandarin (1988)

James Hong (The Mandarin)

as The Mandarin in The Invincible Iron Man: Rise of The Mandarin (1988)

James Woods (Young)

as Iron Man in The Invincible Iron Man: Rise of The Mandarin (1988)

R. Lee Ermey

as J.Jonah Jameson in The Amazing Spider-Man: Vulture’s Shadow (1987)

Gregory Peck

as Uncle Ben in The Amazing Spider-Man: Vulture’s Shadow (1987)

Angela Lansbury

as Aunt May in The Amazing Spider-Man: Vulture’s Shadow (1987)