DeRosa got his start in the business at an open mic at the Laff House in Philadelphia. In 2010, DeRosa released his first album, The Depression Auction, which was released on Comedy Central records. A second album, Return of the Son of Depression Auction, followed in 2011. A third album, You Will Die, was released in September 2013.
In 2012, he co-authored the book Cheat: The Man's Guide to Infedelity with fellow comedians Bill Burr and Robert Kelly.
In October 2013, DeRosa moved from New York City to Los Angeles to take a job as a writer on The Pete Holmes Show.
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