Suggestions by @sunmartsam

Dick Van Dyke

as George banks in Mary Poppins 1970

Score: 0

Tim Curry

as Constable Jones in Mary Poppins (1954)

Score: -1

Dick Van Dyke

as George Banks in Mary Poppins (1954)

Score: 0

Jacen Wilkerson

as Charlie Bucket in Willy Wonka & The Chocolate Factory 1972

Score: +1

Jack Albertson

as Grandpa Joe in Willy Wonka & The Chocolate Factory 1972

Score: +2

Johnny Depp

as Willy Wonka in Willy Wonka & The Chocolate Factory 1972

Score: +1

Tim Curry

as Daddy warbucks in Annie 1983

Score: +1

Celine Smith

as Annie in Annie 1983

Score: 0

Michael Douglas

as Uncle Albert in Mary Poppins 1965

Score: +1

Adrian Hall

as Mike in Mary Poppins 1965

Score: +1

Adrian Hall

as Jane in Mary Poppins 1965

Score: +1

Heather Ripley

as Jane in Mary Poppins 1965

Score: +1

Helena Bonham Carter

as Mrs Banks in Mary Poppins 1965

Score: +1

Dick Van Dyke

as Mr banks in Mary Poppins 1965

Score: 0

Tim Curry

as Bert in Mary Poppins 1965

Score: +1

Omar Sharif Jr.

as Bert in Mary Poppins 1965

Score: -1

Holly Robinson Peete

as Mary Poppins in Mary Poppins 1965

Score: +1

Walt Disney

as Director in Mary Poppins 1965

Score: +1

Holly Robinson Peete

as Mary Poppins in Mary Poppins 1970

Score: +1