Upon graduating, Barry moved to New Orleans and played with many of the city's notable musicians while studying for his Masters degree at the University of New Orleans under the tutelage of Roland Guerin. Currently he is a resident of Washington Heights and making his presence felt on the New York Jazz scene.

In 2011 he joined the Glen David Andrews Band and appeared on several on the band's albums as well as serving as musical director on the album "Redemption". Barry then joined Jon Batiste and Stay Human in 2013 and has performed on the Late Show with Stephen Colbert and a variety of festivals including the Montreaux, Montreal, Newport, North Sea, Monterey, Umbria, and Playboy Jazz festivals as well as Bonnaroo and Lollapalooza. In 2014, Jon purchased a tenor banjo for Barry and had him learn and play it thirty minutes prior to a performance on NPR.

Barry has been known to lead and compose for bands in various genres of music. In 2011, he was awarded the ASCAP Foundation Louis Armstrong Award followed by the Svenson Composition Award in 2012. In March of 2015, he released his debut jazz album Basic Truths featuring original compositions and is in the process of finishing his second album while touring with the Grammy nominated drummer/vocalist Jamison Ross, vocalist Jazzmeia Horn, and others while maintaining an active performance schedule around New York City.