Winston Smith's 1979 Alternative Tentacles record label logo is one of my favorites. I bought an Alternative Tentacles T-shirt in the early 1980s and wore it until it fell apart in 2011 (my 16-year-old daughter now wears it every day as her homework shirt).
Mark Frauenfelder is the founder of Boing Boing and the editor-in-chief of MAKE and Cool Tools. Twitter: @frauenfelder. His new book is Maker Dad: Lunch Box Guitars, Antigravity Jars, and 22 Other Incredibly Cool Father-Daughter DIY Projects