38. Lee Harvey Oswald In JFK (1991)

Assassinated By: Jack Ruby
Cause of Death: Gunshot

For those who were too busy chasing tail to pay attention in history class, Jack Ruby was the nightclub owner who bucked down President John F. Kennedy's assassin, Lee Harvey Oswald, as Oswald was being escorted through police headquarters.

In Oliver Stone's JFK, Ruby isn't a major character, but what makes the brief depiction of Oswald's death so memorable is the fact that Ruby is played by Brian Doyle-Murray—as in, Bill Murray's older brother. Aside from JFK, Doyle-Murray's credits included nothing other than classic comedies (Caddyshack, Wayne's World) and not-so-iconic ones (Cabin Boy, Jury Duty). The casting is bizarre, especially since Doyle-Murray looks nothing like the real Jack Ruby. Maybe Oliver Stone just loved the actor in Sixteen Candles as much as any teenage girl in the '80s.

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