Mr. Show (suggested by Jamie McBain) 5

Brilliant, very twisted, extremely clever sketch comedy from Bob Odenkirk and David Cross (although I don't always agree with their solo stand up comedy from a political standpoint) that makes me laugh more than any other programming on TV. Most people I show this to just don't get it and never will...a few others don't get it the first couple of times through, but eventually get it and thank me for it non-stop. Those that don't get it or won't give it a chance are truly missing out. Ran on HBO in the mid to late 90's.