Joel on Software
Joel Spolsky was an employee at Microsoft in the early 1990's as a manager in the Excel group, and has been blogging about software and running Fog Creek Software since 2000.

Stevey's Blog Rants
Steve Yegge was an employee at Amazon.com and now works for Google. He's a smart guy, and knows more about programming than I would if I studied for 168 years.

Cafe au Lait
Elliotte Rusty Harold has written more books than I've read in my life I think. He teaches at Polytechnic University in Brooklyn and was cool enough to post a Java course he teaches on his site.

Signal vs. Noise
Authored by the guys at 37 Signals, this blog covers a variety of topics on development, design, and the business of making software and web applications.

Stack Overflow
I've been listening to this one (usually during a long late night walk around my neighborhood in south Austin with a ½pint of Jack) ever since it started in mid-April of 2008. The hosts are Joel Spolsky and Jeff Atwood, and they talk about software development and various cool things of interest to programmer/developer geeks. I highly recommend it!

Diggnation
Kevin Rose and Alex Albrecht, formerly of The Screen Savers on Tech TV, put on this weekly show and discuss geek things while drinking import beer. Kevin also started the popular Digg news site in 2005.

NerdTV
Interviews with current and historical tech people by Robert X. Cringely. Most of his shows are really interesting, with the exception of one (episode #9). And a new season is about to come out soon too, woo. Bob Kahn and Andy Hertzfeld are my favorite episodes.

InfoWorld Daily
Technology news every day with host Tom Sullivan.

The MicroISV Show
Michael Lehman, the MicroISV Evangelist, and Bob Walsh, author of �MicroISV: From Vision to Reality�, co-host a weekly interview show featuring developers who both develop the software and run their own businesses.

Ruby on Rails Podcast
News and interviews about the Ruby language and the Rails website framework, hosted by Geoffrey Grosenbach. I like a lot of the interviews, but sometimes you have to choke down some elitist dumbassery (like pointless shit-talking about PHP and other non-Ruby languages), but there are still some good discussions to be heard here.

Grid7 VentureCast
Bi-weekly podcast with interviews of local Arizona tech entrepreneurs, hosted by Sean Tierney.

BoagWorld Podcast
A couple of limey's "talking about news and advice on website design and management without overwhelming you with techno babble." Can be entertaining, although somewhat lacking in geekier tech content.

User Friendly
This is a cool Internet based cartoon I've been following since 1998 or 1999. "Pitr" is my favorite character. Check it out.

Dilbert (of course)
If you're a fellow cube dweller you too probably enjoy Dilbert. This link is for those who've been living in a cave the last 10 years.

I, Cringely
Robert X. Cringely was an early employee at Apple in their garage days, and later went on to become a tech journalist. He has made some great videos too, Triumph of the Nerds and Nerds 2.0.1

Paul Graham
Paul Graham founded Viaweb with the infamous Robert Morris, sold it for millions to Yahoo! in 1998, and has since been writing interesting essays on tech starups, and even funding a few.

TechCrunch
Since June of 2005 TechCrunch has been profiling new and existing tech companies. The site is written in a "blog" style and edited by Michael Arrington.

Valleywag
Valleywag is a tech news and silicon valley "gossip" site. There's usually something interesting on it.