Frank Morgan as Professor Marvel, The Wizard of Oz, The Gatekeeper, The Carriage Driver, & The Guard
Words can't even describe this one. Just watch it.
The Parent Trap (1961 & 1998)
(1961) Haley Mills as Susan Evers & Sharon McKendrick
(1998) Lindsay Lohan as Hallie Parker & Annie James
No, Lindsay Lohan does not have a long lost twin sister.
Back To The Future II (1989)
Michael J. Fox as Marty McFly, Marty McFly Jr., & Marlene McFly
Thomas F. Wilson as Biff Tannen & Griff
Back To The Future is my favorite movie of all time and the pretty seamless editing of the scenes wherein two roles played by one actor met was exceptional considering the technological advances then.
The Nutty Professor (1996)
Eddie Murphy as Sherman Klump, Buddy Love, Lance Perkins, Papa Klump, Mama Klump, Grandma Klump, & Ernie Klump
The Nutty Professor is one of those timeless movies that I wouldn't mind watching again and again. Eddie Murphy playing 7 roles all at the same time was priceless.
Austin Powers: International Man Of Mystery (1997)
Mike Myers as Austin Powers & Dr. Evil
These were not the only roles he played, Mike Myers played a lot more in the following Austin Powers movies, but they are definitely the most iconic!
Nicolas Cage as Charlie Kaufman & Donald Kaufman
This one was pretty seamless. One massive thumbs up to this whole movie.
The Lizzie McGuire Movie (2003)
Hilary Duff as Lizzie McGuire & Isabella Parigi
This was a massive part of my childhood years. Lizzie and Isabella's performance at the end was beautiful!
Charlie and the Chocolate Factory (2005)
Deep Roy as all the Oompa Loompas
At some point in my life, I was genuinely confused as to how they made all these oompa loompas happen but now I know that we can thank Deep Roy and some editing sorcery for it.