Jessy James of Miami, Florida was born on May 29, 1986. Jessy was always a curious child always wanting to discover and master things. Early on with his father passing away, he looked up to his older brother, who inspired him to pursue rap. Throughout his early years, Jessy was in rap groups like “South Side Brigade” and “Street Rep”. Upon his family moving out of Miami, Jessy was not adjusting to the abrupt move. He acted out and became known as a trouble maker, however, his passion for rap never stopped. With little interest in school Jessy would sometimes skip and go to the studio instead. Still focused on his rap career, Jessy joined forces with Dreadwood Entertainment alongside recording artist Jimmy Dade.
Following a brief hiatus, Jessy has dropped singles such as the Jimmy Dade produced “Twerking”, and memorable tracks like “Michael Prophete”, “May 29” and “2 da Head”. Finally, Jessy James is prepared to release a highly anticipated project entitled “U.G.L.Y” which is an acronym for “You Gotta Live Young”. Fueled by records such as “Ride”, “Hardaway” and the latest single “Ain’t Real No More”, “U.G.L.Y.” should prove to be able to live up to the anticipation. With collaborations only from Jimmy Dade and fellow Miami artist, Billy Blue, Jessy will continue to convey his street message through his impetus yet gritty style. Moving forward, time will prove Jessy James’ longevity..