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ended up going with SuperBad. I've rewatched it more times.
Other
The answer is Movie 43
I was going to give you grief for forgetting about Office Space, but apparently it was made in 99 (God I'm getting old).
Borat gets my vote - while it didn't live up to the individual skits, it was hilarious and significantly influenced pop culture. For at least a year, "Is nice" and "Jew claw" were part of the public lexicon.
Office Space would have been my top pick if it was on that list too. Have you seen Mike Judges new series that's on HBO? It's called Silicon Valley and it's hilarious. If you liked Office Space you'll like Silicon Valley.
Silicon Valley and Mr. Robot are pretty much the only shows I watch right now
Anchorman with Road Trip as a close second. Road Trip is a very special movie to me, hilarious and endlessly rewatchable but also very nostalgic for me as it was one of me and my friends' favorite movies when I was younger.
Anchorman, though, is just one of the funniest movies ever made. I actually fell out of my chair in the theater and was on the disgusting movie floor on my hands on knees desperately gasping for air the first time I saw it. And it's a credit to its comedic genius that it still cracks me up to this day, thousands and thousands of rewatches later.