Cobi became interested in music at about age eight. When a family friend visited their home with an electric guitar, then he began to teach Cobi and his brother a few chords. Once he was able to play them, his interest in music grew. That summer, he bought his first guitar, a
Squier Stratocaster, by saving up money made from mowing lawns for $3 an hour. From then on, he taught himself to play guitar by ear, listening to songs over and over until he mastered them. Shortly after, Cobi and a long time friend formed a
blues band, playing
covers of songs at local bars in
Minnesota and
Wisconsin. Cobi is an alumnus of
Berklee College of Music in Boston. In 2008, Cobi and five others formed the band Gentlemen Hall. The success of the band, which was signed to
Island Def Jam Records, came rather quickly. In 2009, Gentlemen Hall won a
MTV Video Music Award for Best Breakout Boston Artist, and the band performed at the 2011
Billboard Music Awards. In 2012, Cobi sang
The Star-Spangled Banner at a
New England Patriots game. On May 3, 2016, Cobi released "Don't You Cry For Me", which premiered through
Interview Magazine. The track was later released through digital retailers and streaming services
Spotify,
Google Play,
iTunes,
Apple Music, and
Amazon Music on May 6, 2016. In July 2016, the track was trending on Billboard's and Spotify's Viral 50 list. A music video for the song was released in September 2016 and premiered through the
Huffington Post. As of October 2016, the song had over 12million streams on Spotify since its debut in May. On September 29, 2016, Billboard premiered his second single "Prophet Story". Billboard also premiered the music video for "Prophet Story" 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. In November 2019, he released the single "Island In My Mind". In January 2020, he released the single "No Way Out". In March, he released the song "Keep Climbing". In May, he released the song "Don't Stop". ==Artistry and influences==