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I started watching Mad Men recently, and find it to be amusing. I've only watched two episodes, and it's a bit over the top in portraying everyone in the 50s as fucked up racist drunkards, but I'd still suggest it.
See also:
NewsRadio
Strangers w/ Candy
Profit (only 6 were made including the 2 hour pilot, but it was brilliant)
Home Movies (It's a cartoon, but it's one of those 'adult' cartoons - if you don't like to think or cartoon characters that use big words, skip it)
Black Books (This is british, and fairly slapstick-comedy, but everyone loves it)
Action! - Only one season was made, damn it. Loved it.
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