In 2008, George appeared at Brandeis University with his comic poetry. His performance was noted to be one of the best. The next year, Boston Globe wrote an article about the young poet. He was becoming more and more popular in Massachusetts and beyond.
In 2009, George decided to try his rap skills. He released a 15-track hip-hop album called Watsky. The most successful single from the album was “Stupidass”, however, it failed to make it into the popular chart. A year later, the artists released his next album, Guilty Pleasures, which was available for free downloading at Watsky’s official website. The same year, he became one of three poets, who got a chance to perform live on the FOX channel during NAACP Image Awards ceremony.
In the summer of 2012, Watsky presented a free mixtape, Nothing Like The First Time. In July, he went on a tour with the same name to promote the album. George traveled to New York, Chicago, Atlanta, Boston, LA, and Jacksonville. After that, he released a live album Live! На Troubadour, which featured his performance in Los Angeles as part of the tour.
In 2013, Watsky announced his next LP, Cardboard Castles, and a new tour planned for 2014. He was planning to visit all large cities in the USA and Canada. The lead single from the new LP was “Strong As An Oak”. Later, he presented “Moral of the Story” and “Hey, Asshole”, both of which were successful. The album itself reached the 23rd spot of Top Heatseekers Chart. Many clubs tried to book George Watsky for private events.
In the fall of 2013, the tour Vans Warped was paused due to Watsky’s unexpected behavior at one of the concerts. While performing in London, George climbed to the rigging, which was over 30 meters tall and jumped down to his fans. The public cleared the way and Watsky fell to the floor. The musician was lucky enough not to get hurt. One of the fans, though, broke her arm.
In 2015, Watsky announced the release of his next live album, All You Can Do: Live From The Regency Ballroom, which was recorded during All You Can Do tour. In July 2016, the artist presented a new LP, x Infinity, and embarked on a tour of the USA and Europe. The album’s producer was Kush Mody.
At the end of 2016, George recorded a single for Lin-Manuel Miranda’s project The Hamilton Mixtape. Watsky already worked with Miranda a year before at Ham4Ham show. He performed “An Open Letter” with Shockwave.
In the spring of 2018, Watsky worked with the band Invisible Inc, with which he sometimes performs. They released a single “Fine Print”, and went on a tour. In the summer, George presented a new single “Welcome to the Family" and announced working on a new album.
Watsky’s latest LP, Complaint, came out in January 2019. The artist continues recording new songs and performing live worldwide.