I can't talk about podcasts without talking about PODCAST HALL OF FAMERS, Dawn Miceli and Drew Domkus. They've been going strong since September 2004 and I've been listening since mid 2005. A show about two crazy kids in love and their adventures in life, both exotic (they lived in Costa Rica for a year and a half and volunteered at the Sloth Rescue there, Dawn became the drummer for her favorite band Rasputina and went on tour with them, Drew has turned his love of skateboarding into his own company "Old Dude Skating") to the mundane (day to day life on their farm in Wisconsin, a simple trip to the Wal-Mart might be the focus of an episode). We've followed them through many ups and down. But, their sense of humor remains strong and is the hook of the show (whether it be the running long time inside jokes of such things as Dawn's fixation with the sound of the words "Buy American", or calling for reservations at the fictional Soylent Green cannibal restaurant, "Bubbling to the Top", "Interupting Robot" (and other phrases that I guess you've had to be there to understand)). Over the years, they've both become not just people on the computer but actual friends and I know that my life would be different without them in it.
EDIT : The following I wrote on Apr 27, 2012: I almost can't believe that I've been listening to this show for SEVEN years...has it really been that long since I first discovered "Dawn and Drew"? This couple still make me laugh all these years later. The audio quality of the early episodes isn't nearly what it is now, so if you go back into the archives, don't judge them by today's standards.
What used to be a show about a couple living on a farm in Wisconsin and their daily "adventures" around the farm has morphed over the years. Now the focus is on Drew staying at home on the farm while Dawn tours the country as a drummer with the band, Rasputina. They've gone through so many actual adventures with their multiple siblings, multiple pets, Dawn's nephews and both sets of their parents and they include us, the listeners all along the way with them.
I've still yet to actually meet them (at their annual "Dawn-A-Pa-Drew-Za" party or elsewhere), but I consider them both lifetime friends!