Suggestions by @willykevin

Chris O’Donnell

as Peter Parker in MCU 90's (Reboot)

Score: +3

Johnathan Brandis

as Anakin Skywalker in Star Wars Prequels Trilogy (1990s Recasted)

Score: +2

Sylvester Stallone

as Dominic Toretto in Fast & Furious 90s

Score: +2

Tupac Shakur

as Roman Pearce in Fast & Furious 90s

Score: +1

Michael J Fox

as Deadpool in Deadpool (1988)

Score: 0

Willem Dafoe

as Norman Osborne/Green Goblin in Spider-Man 2002 (not all but some recasting)

Score: +1

Cliff Robertson

as Ben Parker in Spider-Man 2002 (not all but some recasting)

Score: +1

Rosemary Harris

as May Parker in Spider-Man 2002 (not all but some recasting)

Score: +1

J.K. Simmons

as J Jonah in Spider-Man 2002 (not all but some recasting)

Score: +1

Gary Oldman

as Norman Osborne/Green Goblin in Spider-Man 2002 (not all but some recasting)

Score: +1

Tobey Maguire

as Peter Parker/Spider-Man in Spider-Man 2002 (not all but some recasting)

Score: 0

Hayden Christensen

as Harry Osborne in Spider-Man 2002 (not all but some recasting)

Score: +1