For anyone who doesn't know, Jonathan Coulton is a singer-songwriter of very varied and often geeky talent. He tried an experiment to write and record a new song every week for a year and the results were quite good.
Other geeky Coulton songs of note are Code Monkey, Mandelbrot Set and De-Evolving.
Additionally, the band Hard 'n Phirm (not porn, I swear) produced a really good album with Horses and Grasses. You can sample some of their music here.
My wife is a huge Harry Potter buff and absolutely loves the group Harry and the Potters, who are accredited with creating Wizard Rock. You can listen to some of their songs here. We went to one of their concerts (at a local, public library) and it was a blast. They're crazy energetic and my inner nine-year-old got a kick out of being loud in a library. She also likes Draco and the Malfoy's who happen to be touring with HatP's right now.
This site is awesome and has filled about a third of my playlist at work. Here talented people upload their remixes, technos and re-inspirings of video game music. Metroid and Legend of Zelda alone have in excess of 110 songs and everything is free and legal to download. You can even search by console in case you want songs from Virtual Boy or Sega Saturn games. My favorite is the Toejam and Earl redo.
They Might Be Giants are certainly worth mentioning. Their website, which is normally quite awesome, seems to be having difficulties so I guess I can only link to this nice video version of one of their songs. In truth I prefer Weird Al's "Bob" to TMBG's "I Palindrome I" because Weird Al's song is actually comprised of palindromes. Also, Weird Al's White and Nerdy needs to be included for reasons too numerous to mention.
If you have an ear for classical composition than PDQ Bach is a real hit. The artist Peter Schickele pretends to be a historian who keeps uncovering works by J. S. Bach's forgotten son P.D.Q., which are either direct parodies of classical pieces (such as The Short-Tempered Clavier, Preludes and Fugues in all the Major and Minor Keys Except for the Really Hard Ones) or zany style-parodies (Grand Serenade for an Awful Lot of Winds and Percussion). Wikipedia describes him as "the INTERCAL of Baroque music."Sadly, I couldn't find anywhere to preview the music.
I'm fond of Roy Zimmerman, but his forte is political satire. I will say that he does a masterfull job of weaving pointed criticisms into really solid music. You can sample his music here.
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