It is precisely its non-bloggyness that makes The Audacity of Despair such a worthy and memorable read. On it, Baltimore's favorite curmudgeon (and, needless to say, the creator of The Wire) does the whole blog thing, but on his own terms-that is, he rambles on, goes obscure, and isn't afraid to make the kind of complex political arguments that other people keep insisting that the internet has made obsolete. And though Simon seems as grouchy as always, it's also possible to detect a glimmer of glee as he tackles subjects ranging from Mitt Romney's tax rates to the Leaning Tower of Pisa to the odd behavior of Baltimore pigeons. Updated on more of a fortnightly than daily basis, the Audacity of Despair is the most bookmark-worthy site we've come across in a while.
Runners-Up!Best Blog2. Bmore Music (bmoremusic.net)
3. City That Breeds (citythatbreeds.com)
4. The Comics Curmudgeon (joshreads.com)
5. The Mobtown Shank (sugarfreak.typepad.com)