My first "real" job was an internship at SPY magazine, back in the late 1980s. Upon graduation, I joined the staff as an art director, and got to work with some legends: B.W. Honeycutt, Kurt Andersen, Graydon Carter, Tom Phillips, as well as some legends in the making, like Christiaan Kuypers and Michael Hainey (hi guys). It was the best job I've ever had – it taught me pretty much everything I know about editorial design, journalism, and most of all, humor.
Kurt has posted a nice little slideshow of the SPY covers. I worked on a bunch of the later ones.