The real problem with this question is the idea of what makes something a classic.  Is it just time?  How much time?  Are we to the sad point where 80s movies are now classics?

Ooof.

So I went with the understanding that I’m looking pre-1980 as a restriction factor (to reduce that crushing feeling of getting old).  It eliminates all nostalgia from the situation, as I couldn’t have seen anything prior to early summer 1979.  So gone are all of the John Hughes movies I could put up here.   As are Empire Strikes Back, any Indiana Jones movie, Bladerunner, Aliens, and other nerd staples.

And I really didn’t want to go with the standard I’m-an-awesome-film-guy responses like Citizen Kane or The Godfather (or even Barry Lyndon if I wanted to be uber-cine-douchey).  I hope have proven the scope of my movie knowledge by now (if not, go F yourself) so I can avoid putting the true classics up there (although some of these are).  I went with movies that I still enjoy today as much as I did when I first saw them.

1.  Butch Cassidy and the Sundance Kid (1969…ha ha)
Director:  George Roy Hill (bad ass)

Unbeknownst to me, I apparently love Paul Newman.  When I started pondering this query, I found no less than 5 movies of his I could argue for and sound reasonable.   But Newman and Robert Redford are so friggin’ good as Butch and Sundance that I found it impossible to exclude.   Both are so comfortable on-screen and in their characters that it just seems effortless.  Not to mention one of the greatest endings in cinematic history (I will argue to this day about that one).

2.  The Hustler (1961)
Director:  Robert Rossen

Yep, another Newman one already.  But I love shooting pool.  The sound of the break is one of those sounds that I find so soothing, like bowling pins or a good golf swing.  This movie illustrates (and probably influenced) why.  It’s the same reason why Frank Sinatra and Dean Martin are some of my favorite dudes ever.  They just exuded cool like The Hustler does.  Fast Eddie Felson makes my all-time characters list and Jackie Gleeson is brilliant as Minnesota Fats.    (Note: I even enjoyed the sequel The Color of Money, if only to see Eddie shoot again.   OK, the fact that Scorsese directed it definitely helped.  And the fact that Tom Cruise was supposed to be a douche…like he is in real life.)

“I don’t rattle, kid. But just for that I’m gonna beat you flat.”

3.  Young Frankenstein (1974)
Director:  Mel Brooks

I love me some Mel Brooks too.  I could have easily put Blazing Saddles here and been done with it.  I had seen most if not all of Mel Brooks’ filmography at a shockingly young age, courtesy of my older brother.   But the only thing that may trump my complete adoration for Mel Brooks is my love of Gene Wilder.  I just enjoyed his performance as Dr. Frankenstein so much that it trumps even Willy Wonka or Jim in Saddles.  I can still slip quotes from this movie into conversations with any male in my extended family and get a chuckle.  Added with Peter Boyle, Marty Feldman, Madeline Kahn, Cloris friggin Leechman, you can’t put funnier people together.

And Teri Garr may be partially responsible for me becoming a man.  What?  Just saying…she was hot back then.

4.  The Sting (1973)
Director:  George Roy Hill (told you he was bad ass)

Yep, another Paul Newman & Robert Redford movie.  But now you take that brother-like chemistry between them add in the always awesome Robert Shaw (Quint from Jaws) and make it a 1930s overly elaborate heist movie.   Sold.  Seriously, go watch it right now.

5.  Chinatown (1974)
Director:  Roman Polanski

Growing up reading a lot of Sherlock Holmes, I developed a love for a good detective story.  I like the evolving mystery where the film follows the detective around and you as the viewer discover the clues as he does (Polanski actually removed a voice over narration to further this effect).  And in this case, that detective is Jack Nicholson, being his smarmy, captivating self.   The script is considered by some to be the “perfect screenplay” and is used as a teaching tool.   And it was only nominated for like 47 Oscars (note: not researched), so I think I can safely recommend it.   Unless you don’t like awesomeness.

Honorable Mention (which are basically just additional suggestions for viewing):  Blazing Saddles, Alien, One Flew Over the Cuckoo’s Nest, Monty Python and the Holy Grail, Jaws, The Exorcist, Dr. Strangelove, Dawn of the Dead, Marathon Man, The Conversation, The Great Escape, Seven Samurai, North by Northwest, Strangers on a Train, The Third Man, History of the World: Part 1