Going freelance in 1981, O'Rourke's writing appeared in "Playboy," "Vanity Fair," "Car and Driver", and "Rolling Stone". He became foreign-affairs desk chief at "Rolling Stone", where he remained until 2001. In 1996, he served as the conservative commentator in the point-counterpoint segment of "60 Minutes". During the Bosnian genocide, O'Rourke received criticism for using the American public's lack of interest in Bosnia as a way to joke about "unspellables killing the unpronouncables."