Suggestions by @jasleenfaydelarosa

Ben Hanscom

as Dan Schneider in Which characters should actors have played in the 80’s?

Ken Smith

as Dan Schneider in Which characters should actors have played in the 80’s?

Isaac Henderson

as Ron Lester in Which characters should actors have played in the 90's?

Chelsea Briggs

as Ron Lester in Which Character Should Actors Have Played Genderswapped in the '90s

Ron Lester

as Thomas in Lisa Frankenstein (1999 Genderswapped)

Tamara (Lisa Frankenstein)

as Ron Lester in Which Character Should Actors Have Played Genderswapped in the '90s

Ron Lester

as Martin "Dumptruck" Dunnstock in Heathers (1999 Genderswapped)

Damian Leigh

as Ron Lester in Which characters should actors have played in the 90's?

Ken Smith

as Ron Lester in Which characters should actors have played in the 90's?

Ben Hanscom

as Ron Lester in Which characters should actors have played in the 90's?

James Van Der Beek

as Henry Bowers in It ('90s Teen Cast)

Brad Renfro

as Stan Uris in It ('90s Teen Cast)

Lamont Bentley

as Mike Hanlon in It ('90s Teen Cast)

Freddie Prinze Jr.

as Eddie Kaspbrak in It ('90s Teen Cast)

Ron Lester

as Ben Hanscom in It ('90s Teen Cast)

Sridevi

as Rahima in Love, Victoria (80s Genderswap)

Harold Ramis

as Danny Friedman in You Are So Not Invited to My Bat Mitzvah (80s)

Samantha Logan

as Willa Earp in Wynonna Earp (1986-91)

Winona Ryder

as Waverly Earp in Wynonna Earp (1986-91)

Lori Loughlin

as Wynonna Earp in Wynonna Earp (1986-91)