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Watsky has performed on both coasts an lead emcee with his band Invisible Inc. The trio's self titled album, a blend of jazz and hip hop featuring R&B sensation Passion, was selected as an Amoeba Music staff pick. In 2009, Watsky will release his solo music CD, featuring guest appearances by fellow HBO Def Poets Dahlak and Rafael Casal, singers Danny McClain, Mieka Pauley and once again, Passion. Watsky has served as an on-air personality on WERS 88.9 FM's 889@Night since early 2007.

Watsky has made strides to bring his poetic sensibilities to the theater world. His one-man show, So Many Levels has been presented in Boston, San Francisco, Vermont and at the Hip Hop Theater Festival Critical Breaks series in New York City. He has been featured additionally at the San Francisco and Washington, DC arms of the Hip Hop Theater Festival. He played the title character and co-wrote a 2004 adaptation of Dante's Divine Comedy for the Living Word Festival and his stage play Harold's Fall was the recipient of the 2009 Rod Parker Playwriting Fellowship. Making his way to the page, George's debut poetry collection and CD, Undisputed Backtalk Champion, was published by First Word Press in 2006. Edited by novelist Adam Mansbach, the book is currently in its fourth printing.

Watsky has also emerged as part of a vanguard of artists involved in the sustainability movement. The inaugural Speak Green winner for poetry on climate change, Watsky has twice been invited to perform in Sundance, Utah by Robert Redford. His work has brought him to perform at the opening plenary of Green Cities 2008 in Sydney, Australia, and Greenbuild Chicago, where he took the stage immediately before President Bill Clinton.

Touring while finishing his college education on a condensed schedule, George has performed at conferences and universities in more than half the states in the country, and two in Australia. He has performed at some of the nation's most notable venues, including the Apollo Theater, the Kennedy Center Concert Hall, the San Francisco Opera House and the Shrine Auditorium. He has shared billing with Beyonce, Stevie Wonder, Bonnie Raitt, and Mohammed Ali among others.