Suggestions by @jamesbess

John Cazale

as Mr Pink in Reservoir dogs 70s

Score: +1

Jack Nicholson

as Frank Slade in Scent of a woman (1982)

Score: +1

Jack Nicholson

as Frank Slade in Scent of a woman (1982)

Score: +1

Matt Dillon

as Biff Tannen in Back to the Future (Alternate Cast)

Score: 0

Rob Lowe

as Drake in Drake and Josh (80s)

Score: +2

Ben Stiller

as Josh in Drake and Josh (80s)

Score: +1

Drew Barrymore

as Megan in Drake and Josh (80s)

Score: +1

Susan Sarandon

as Audrey in Drake and Josh (80s)

Score: +1

Jennifer Connelly

as Megan in Drake and Josh (80s)

Score: +2

Curtis Armstrong

as Craig in Drake and Josh (80s)

Score: +1

Anthony Edwards

as Eric in Drake and Josh (80s)

Score: +1

Whoopi Goldberg

as Helen in Drake and Josh (80s)

Score: +1

Bob Saget

as Walter in Drake and Josh (80s)

Score: +1

Jim Carrey

as Crazy Steve in Drake and Josh (80s)

Score: +1

Johnny Depp

as Drake in Drake and Josh (80s)

Score: +2

Brad Pitt

as Drake in Drake and Josh (80s)

Score: +1

Keanu Reeves

as Drake in Drake and Josh (80s)

Score: +1

Chris Penn

as Chuckie Sullivan in Good Will Hunting 1987

Score: +1

Matt Dillion

as Chuckie Sullivan in Good Will Hunting 1987

Score: +2

Sylvester Stallone

as Jack/ Catuzzi in Chris Columbus Daredevil (1996)

Score: +1