Suggestions by @pakjirasan

Ron Jeremy

as Cuba in The Worst "Hetalia" Live Action Movie

Rudy Pankow

as United States in Hetalia (Live action)

Shawnee Pourier

as Trisha 2 in The Most Popular Girls in School (with Stranger Things cast)

Sydney Bullock

as Trisha Cappelleti in The Most Popular Girls in School (with Stranger Things cast)

Elodie Grace Orkin

as Brittnay Matthews in The Most Popular Girls in School (with Stranger Things cast)

Danielle Panabaker

as Will Vandom (2000's) in W.I.T.C.H. (in Different Decades)

Lisa Bonet

as Taranee Cook (80's) in W.I.T.C.H. (in Different Decades)

Winona Ryder

as Irma Lair (80's) in W.I.T.C.H. (in Different Decades)

Molly Ringwald

as Will Vandom (80's) in W.I.T.C.H. (in Different Decades)

Lisa Pelikan

as Will Vandom (70's) in W.I.T.C.H. (in Different Decades)

Elodie Grace Orkin

as Lyubava (2020's) in Fantasy Patrol (in Different Decades)

Kristen Stewart

as Mary (2000's) in Fantasy Patrol (in Different Decades)

Olivia D'Abo

as Samantha Montgomery in A Cinderella Story (1984)

Karen Fields

as Brianna in A Cinderella Story (1984)

Samantha Logan

as Miranda in W.I.T.C.H. (Live Action 80’s)

Heather Duke

as Karen Fields in Which characters should actors have played in the 80’s?

Leah Kilbourne (Flying)

as Karen Fields in Which characters should actors have played in the 80’s?

Tina Blake (2013)

as Karen Fields in Which characters should actors have played in the 80’s?

Amber Fairfax

as Meaningful Name in Sort by Tropes

Amber Fairfax

as Queen Bee in Sort by Tropes