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These are probably the two funniest movies to come out in the last 10 years. Tough.
Although the Hangover made me laugh harder the first time I saw it, I think Old School has more replay value.
The Hangover hands down... It was way funnier for me.
Neither one of these is my cup of comedy tea. I found Old School to be slightly more funny but I thought The Hangover had a better story. They are kind of even in my mind. I wouldn't watch either one of them again.
It's probably unfair, but The Hangover's sequel was so awful that I can't view the franchise objectively anymore.