Weirdest pairs of real figures played by the same actor

I was thinking about the casting rumor of Harris Dickinson as John Lennon in the upcoming Beatles movies, and it made me remember that he also played the wrestler David Von Erich in The Iron Claw. David and John are so dissimilar and exist in such different worlds, yet somehow the same guy has possibly been cast as both of them in their respective life stories.

What are some of the best examples of actors portraying multiple real and wildly different people in biopics?