Harry originally started playing guitar live in 2006 when living in Rome, Italy. Harry Sills Live broke onto the scene in bars around Boston in 2008 and joined up with Jeff Harrelson to form HSL in 2010.

HSL's shows feature mostly cover songs along with originals such as "Reason to the Rhyme", "Fallen So Long", "Get Some" and "Roadtrippin". From country to hip-hop, HSL brings over 3 hours of music to each show.

HSL's first studio album is tentatively scheduled to be recorded by the end of 2013.