Dreamweaver
I just opened Dreamweaver CS5.5, and I literally got chills. Do people actually pay money for this, let alone use it to design modern websites? When was the last time it changed? 2003?
UPDATE: I visited Adobe’s Dreamweaver page, but I couldn’t figure out what they were trying to say because half of it was in Flash. I think Adobe needs to pull their heads out of their asses and bring their software into this decade (or in some cases, this millennium). They have some great software (Audition and Premiere, for example), but some of it looks like it came from Mac OS 9. By a 12-year-old. Even their flagship, Photoshop, still looks like ass. (Can’t speak for Windows, but certainly on Mac OS X.)