(Obviously, I leave any CRM related site out of the running here...)
Best Radio-Themed Blog/Website:
Rick Kaempfer's Chicago Radio Spotlight
This site features Rick Kaempfer, a 20+ year veteran of Chicago radio, interviewing different Chicago radio personalities (both past & present) each weekend. Rick is an excellent interviewer, always bringing out the best answers in his subjects. The interviews are always upbeat, never negative in tone, and are filled with both terrific inside information and a heart-felt love for local radio. A must read each Saturday.
Best Television-Themed Blog/Website:
Terence Henderson's The T-Dog Media Blog
While T-Dog's site also covers local media besides television, TV is the site's top focus. It always has the biggest TV news mentioned, along with his usually right-on commentary. Always enjoyable.
Best Newspaper-Themed Blog/Website:
Michael Miner's News Bites
This blog, which resides within the website for the Chicago Reader, is all about Chicago's print media. Written by Michael Miner, who also contributes the Hot Type column each week for that paper, he keeps a close eye on all of the happenings surrounding Chicago's papers. As a longtime admirer of newspapers, he's quick to point out problems plaguing the industry he loves and those who seem to damage it more. He is also quick to point out positive changes within it on his blog. Sadly, in 2008, there were more problems to point out than positive changes. Regardless, he did so extremely well.
Best Media Blog/Website About... Whatever...
Eric Zorn's Change of Subject
Located within the Chicago Tribune's website, Eric Zorn's blog gets extra points for being one of the very first of its kind. It has suddenly become common place for newspaper columnists to also have blogs (and even more recently, Twitters, Facebooks, etc.), but Eric Zorn was way ahead of the curve, having his Change of Subject up on the Internet years ago. Zorn, a columnist for the Trib's Metro section and a former Media columnist, writes about... well... just about anything, and sometimes about almost nothing. In this blog he covers media, popular culture, Internet stories & links, politics, his own columns, whatever floats his boat that particular day. It's the online print equivalent to a Seinfeld episode. It is also equal parts fun, thought-provoking, informational and enjoyable.
Most Fun Media-Related Message Board:
Chicago Sports Fan Message Board
Sure this site talks about Chicago sports teams and many other subjects, but the biggest focus on the site is about Chicago Sports Radio. On any given day, at any given moment, there are dozens of posters giving their opinions on local radio. In addition to the posters, there are even more people who are just readers of the site, enjoying the debauchery there. It is negative, ugly, down n' dirty, and every bad cliche that can be thrown out about message boards. At the same time, they wear all that like a badge of honor over there. While it may be all of those things, it is also brutally honest and lots of fun. It is like a virtual neighborhood bar, where everybody has an opinion on sports and will argue that opinion all night long, well past closing time. There is no other site like it in town. (And a bunch of guys on there would gladly argue that there are better messages boards someplace else, just for the sake of arguing. That's what makes it what it is.) Not for the faint of heart or easily offended.
Most Fun Local Media Blog/Website:
Rick Klein's FuzzyMemories.TV
This website is more than a self-described online Museum of Classic Chicago Television; it is a time machine. Here is collected hundreds of hours of classic TV show clips and commercials from the silver age of television to just a few years ago. It has a message board/forum and plenty of historical information about Chicagoland TV. Almost every memory of your childhood TV watching can be found here. Not only do I call it a time machine because it can transport your mind back in years while watching these classic videos, it is also a time machine that seems to warp your current time, because without your being aware of it, it can suddenly be many hours later before you click away from the site. Enjoy the flashbacks!