I dunno man, I think Missed Connections for every city could compete with Best of. Every single Missed Connection for just about every city could seriously be a Best of Craigslist nominee.
Kimmel and Alison Brie do Missed Connections <iframe width="560" height="315" src="//www.youtube.com/embed/koldhwMkrJs" frameborder="0" allowfullscreen></iframe>