A comedic actor and author, he is best known for published works such as The Areas of My Expertise (2005) and More Information Than You Require (2008). He also appeared as a correspondent on The Daily Show with Jon Stewart.
He studied literature at Yale University and subsequently worked as a literary agent in New York City. He first appeared on The Daily Show in 2005.
He appeared in a Mac advertising campaign for Apple, Inc. from 2006-2010.
He was born in Brookline, Massachusetts. In 2000, he published two articles about his mother's death.
He acted in a few episodes of Bored to Death with Jason Schwartzman.