Matt Drudge

Before he became the reclusive multimillionaire pope of the conservative echo chamber, Matt Drudge was a brooding loner at Northwood High School in Silver Spring, Maryland (Class of '84). In his brief Arrowhead yearbook entry he notes his zodiac sign (Scorpo), his favorite color (Caribbean blue), his favorite food (Jalapeno bologna) and his personal motto ("Where there's a will, there's a way"). Stranger still is teen Drudge's melodramatically bitter Senior Class Last Will and Testament statement:

"I Matt Drudge, being of sound mind and body, do hereby leave the following: To my only true friend Ms. thing, Vicky B, I leave a night in Paris, a bottle of Chaps colongne and hope you find a school with original people--And to everyone else who has helped and hindred [sic] me whether it be Staff or students, I leave a penny for each day I've been here and cried here. A penny rich in worthless memories. For worthless memories is what I have endured. It reminds me of a song, "The Funeral Hyme [sic].'" 

The preceding details and more can be found in an excellent Washington City Paper expose of the Internet gossip columnist's school days.