9. The Life & Times Of Tim
Written, produced and voiced by Steve Dildarian, The Life & Times of Tim lasted for three seasons on HBO from 2008 to 2011. The show follows Tim, a hapless mid-20a New Yorker who just cant seem to catch a break in life. Tim constantly finds himself in outrageous, awkward situations and yet he manages to stay calm and collected throughout. He's surrounded by equally funny characters like his stoner co-worker and best friend Stu who's only aim in life is to score with girls (though hes usually unsuccessful) and eat ice cream cake. One of the most memorable characters of the show is most definitely Debbie, the local chain-smoking prostitute who gives Tim advice on everything from relationships to life in general; she also usually shows up wearing the most inappropriate outfits ever, like a bikini in church for instance. The show featured guest voices from the likes of Bog Sager, Aziz Ansari, Jeff Garlin, Bob Saget and Daniel Tosh and is guaranteed to keep you in stitches. Watch this show or else live with the knowledge that you're missing out on something truly wonderful.