- Was fascinated by hobos as a child, and a large section of his first book was dedicated to the topic.
- In eighth grade, he was voted most likely to become editor of the New Yorker.
- Worked as a receptionist for a literary agency after college and eventually became an agent.
- Worked in publishing for seven years before he started working in comedy.
- Became the Resident Expert on The Daily Show in 2006.
- Author of the absurdist-trivia books The Areas of My Expertise and More Information Than You Require.
- Featured as the PC in a series of commercials for Apple computers opposite Justin Long as the Mac.