2004: The Daily Show, Night Two of the Democratic National Convention ("My father was a poor Virginia turd-miner ... ")The 2008 writers' strike impacted the field for this award significantly -- only twelve 30 Rock episodes this calendar year, sixteen of The Office.
2005: South Park, "Best Friends Forever"
2006: The Office, "The Injury"
2007: 30 Rock "The Source Awards"
There were decent episodes of HIMYM ("10 Sessions"), and I did give much thought to Office episodes like the more-painful-than-funny "Dinner Party", "Chairmodel" or "Did I Stutter?" -- especially the last one (fluffy fingers, Newsies), as well as 30 Rock's brilliant last pre-strike episode, "Episode 210" (about which Alan wrote today, with the Jewish donuts and Gladys Knight).
But ultimately, I have to go with a half-hour that aired the same night as "Chairmodel" -- April 17, 2008 -- because Stephen Colbert was in Philadelphia as part of his pre-primary coverage, and, um, folks showed up for an overstuffed genius episode. Go watch the clips of Barack Obama, noted repairwoman Hillary Clinton, and most brilliantly, John Edwards delivering the W0RD, a piece of intentional comedy that almost makes one want to forget the unintentional tragicomedy he provided later in the year. (Also in the episode: a review of the Philadelphia debate and a sitdown with Rep. Patrick Murphy, who isn't as funny, but he's my friend so I'm linking.)
In a year in which political comedy mattered a great deal, Colbert's being a bit too forgotten (and, yeah, the Xmas special was underwhelming), but for that half-hour, the comedic and political universes centered on his set, and he made the most of the opportunity. Tina who?
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