Suggestions by @castingsinmyblood
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Anthony Hopkins
as Prof. Pierre Aronnax in Disney's 20,000 Leagues Under the Sea (1990s)

Lex Luthor
as Topher Grace in What if this actor played

Benjamin Button
as Dean Jones in What if this actor played

Benjamin Button
as Kenneth Branagh in What if this actor played

Captain America (Steve Rogers)
as Brad Pitt in What if this actor played

Alexander The Great
as Heath Ledger in What if this actor played

Lois Lane
as Faruiza Balk in What if this actor played

The Shredder (Oroku Saki)
as Tatsuya Fujiwara in What if this actor played

Howard (Treasure of the Sierra Madre)
as James Doohan in What if this actor played

Howard (Treasure of the Sierra Madre)
as Fred Gwynne in What if this actor played

Captain Nemo
as Erick Avari in What if this actor played

Juror #8 (12 Angry Men)
as Viggo Mortensen in What if this actor played

Mickey Goldmill
as Ed Asner in What if this actor played

Richard III
as David Oxley in What if this actor played

Entei
as Sean Connery in What if this actor played

Simon Wincer
as Director in Disney's 20,000 Leagues Under the Sea (1990s)

Erick Avari
as Captain Nemo in Disney's 20,000 Leagues Under the Sea (1990s)

Kelsey Grammer
as William "Bill" Randa in Kong: Skull Island (1995)

Bryan Cranston
as Brian Keith as Ben Parker in Marvel Live Action Actors as Marvel Voice Actors

David Koepp
as Writer in Disney's 20,000 Leagues Under the Sea (1990s)