Levinson released his first album, 1175 Boylston, in 2006, while a student at Berklee. On the album (which was named after Levinson's address at the time), he supplied the vocals and played piano, trumpet and trombone while his father played guitar, bass and drums on some tracks, with fellow Berklee student Adam Popick supplying the remaining instruments. The single "City With Two Streetlights" spent eight weeks on the CMJ Top 25 charts. Faculty members of the Berklee songwriting department also voted the album's opening track “Sunny Day” the best song of the year. Following the album's release, Levinson played the 2006 International Pop Overthrow Festival, and was named Best Male Artist at The 4th Annual IAMA (International Acoustic Music Awards).
