| Question | Answer |
| Jon Hamm starred in this 2008 SciFi remake | |
| With this actor | |
| Who was also in this 1994 movie | |
| In which the the villian was played by | |
| Who was in this 1956 movie starring James Dean | |
| With this 60's star | |
| | Question | Answer |
| Don Draper didn't sneak out of this fight in this 2002 war movie | |
| With this crazy person | |
| Who was in this 1995 western | |
| With this original star of the TV series | |
| Who was in this 1967 prison movie | |
| With this 60's star | |
| | Question | Answer |
| Hamm was in this movie about a poem | |
| With this dumb actor | |
| Who was in this 2005 picture about a dog | |
| With this actress (who helped raise Superman in '06) | |
| Who was a secret agent in this Hitchcock film | |
| With this 60's star | |
| | Question | Answer |
| Jon Hamm spent some time in Beantown in this heist flick | |
| With this Oscar winner | |
| Who was in this movie about an equestrian orator | |
| With this Sneaker | |
| Who was the youngster in this buddy pic | |
| With this 60's star | |
| | Question | Answer |
| Donnie Draper played a dick in this recent comedy | |
| With this guy who loves black dudes dressed up as White Chicks | |
| Who was a numbered agent in this spy movie | |
| With this rollerballer | |
| Who starred as Mississippi in this western back in '66 | |
| With this 60s star | |
| | Question | Answer |
| Hammer starred in this 2011 box office bomb | |
| With this veteran actor | |
| Who was in this 1990 cold war thriller | |
| With this 60's star | |
| Bonus Question: Name a movie STARRING any of these 60's stars together | |
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