When he was editor of Washington City Paper in the late 1990s, David Carr published a lengthy piece on Matt Drudge “early years.” Staff writer Eddie Dean called his profile “the making of an American outlaw, an alienated young man who grew up in the shadow of the most powerful government in the world …. a look at the larval years of a media bottom-feeder.”
A high school classmate interviewed by Dean says of Drudge:
[In school] he had a real sinister demeanor about him. Most of the girls were afraid of him — he had that I-might-do-something-crazy type of attitude. He always had this disheveled look about him, very unkempt, and he had bad acne and such a hard, mean-looking face. You’ve got to work hard to look friendly with that face. Probably the only reason he talked to me was because I was the only one that didn’t judge the Drudge.
Drudge admits that the teen years were tough on him and school was the ultimate torture—his only regret is that he didn’t drop out way before graduation. (He was 325th out of a class of 350). “I was bored with it all,” he says, proudly declaring that his only extracurricular activities were passing notes and cutting class. “It was rigid, it was stupid, it was a lot like the news coverage now. There’s very little originality going on. Everything I’ve learned I’ve learned on my own. I’m self-taught. I’ve kept some original thinking or what I think is original. [Other journalists] have to listen to an editor saying yes or no. I don’t listen to anybody.”