[2] 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.
When a family friend visited their home with an electric guitar, then he began to teach Cobi and his brother a few chords.
[3] Shortly after, Cobi and a long time friend formed a blues band, playing covers of songs at local bars in Minnesota and Wisconsin.
[5] The tour included dates running through June 2016 at iconic venues such as Royal Albert Hall, The Hollywood Bowl, and the Sydney Opera House.
[14] 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.
His single "Don't You Cry For Me" features a gospel choir providing background vocals, giving the song a soulful sound.