Early Life
Oakley was born William Lloyd Oakley and raised on a farm in Maryland. He was a fan of Mad magazine from an early age, which helped shape his comic sensibility. He attended St. Albans High School in Washington D.C., where he met and became best friends with Josh Weinstein in the eighth grade. The two created the school humor magazine The Alban Antic in 1983. Such would be the length of their partnership; the two often finish each other's sentences. Oakley later attended Harvard University, where he wrote for and served as Vice President of the Harvard Lampoon, working on the famous 1986 USA Today parody issue. He graduated in 1988 after studying American history.
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