A former original member of the Boston-based band Gentlemen Hall, Cobi released his solo single "Don't You Cry For Me" on May 3, 2016 under 300 Entertainment. An alumnus of Berklee School of Music in Boston, Cobi and five others formed the band Gentlemen Hall in 2008. The success of the band, which was signed to Island Def Jam Records, came rather quickly. In 2009, they won a MTV Video Music Award for Best Breakout Boston Artist and performed at the 2011 Billboard Music Awards.
On December 18, 2015, Cobi signed with 300 Entertainment. In April 2016, he joined English progressive trance group Above & Beyond's international tour, providing vocals for many of the songs. The tour included dates running through June 2016 at iconic venues such as Royal Albert Hall, The Hollywood Bowl, and the Sydney Opera House.
On May 3, 2016, Cobi released "Don't You Cry For Me", which premiered through Interview Magazine. In July 2016, the track was trending on Billboard's and Spotify's Viral 50 list. On September 29, 2016, Billboard premiered his second single "Prophet Story", and later the song's music video for on January 17, 2017. On January 23, 2017 Cobi performed "Don't You Cry For Me" on The Tonight Show Starring Jimmy Fallon with members of The Roots, with the New Power Generation's Morris Hayes on keyboards. He released the EP, Songs From the Ashes, Pt. 1, on September 15, 2017.