He began writing for the magazine in 1972, became executive editor in 1973, managing editor in 1976, and finally editor-in-chief from 1978 through 1981. As far as I know, he never contributed anything to NatLamp after 1981.
I was a fan of his work, especially earlier on, in the “golden age” of National Lampoon. This included his work on the fantastic 1964 High School Yearbook Parody and Sunday Newspaper Parody special issues. He seemed to specialize in topics that appealed to me as a male baby boomer, like cars, model kits, and anything to do with boyhood or adolescence (he was issue editor for the infamous and highest-circulation-ever October 1974 “Pubescence” issue featuring the classic Boy’s Life parody and sex-ed comics.). He often collaborated with Doug Kenney in the mid-seventies (including on the yearbook parody) and artist Alan Rose (First Model Car in the Pubescence issue and Battling Buses of World War II in The National Lampoon Encyclopedia).
O’Rourke was a bit of an outsider at the Lampoon, a mid-westerner in the midst of former Harvard Lampooners. But as some of the founders and early major contributors (Henry Beard, Doug Kenney, and Michael O’Donoghue in particular) left in the mid-seventies, O’Rourke took the reins alongside editors such as Gerald Sussman, Tony Hendra, and Sean Kelly, none of whom were Harvard Lampoon alums. Hendra, in his book Going Too Far, doesn’t seem to have liked O’Rourke much, characterizing him as a bit of a hack who often sided with NL publisher Matty Simmons. But I think this is partly because Hendra was a fairly left/liberal Brit who saw O’Rourke as a right-wing reactionary.
In fact, O’Rourke was a libertarian who criticized the right almost as much as he criticized the left.
To be honest, even though I have considered myself a libertarian since the eighties, I never paid much attention to O’Rourke’s post-Lampoon writing career, which, ironically, is what most people now know him for. This is probably because my embrace of libertarianism came after he was at the magazine, and much of his writing and the direction he was taking the magazine in the late seventies didn’t appeal to me at the time. His passing has reminded me of this gaping hole in my libertarian readings. I have some catching up to do.
R.I.P., Peej. If I were still a drinker, I’d raise a glass of fine Irish whiskey in your honor.