Jessie started banjo lessons in 2002, and went on to lead his family's band, "The Baker Boys.
[3] In August 2008 Baker joined the then current IBMA instrumental group of the year "Michael Cleveland and Flamekeeper".
He has also worked stints with Marty Raybon and Full Circle, David Peterson, and Dove Award-winning Cody Shuler and Pine Mountain Railroad.
[4] In February 2011 Jessie moved on to be a part of the award-winning group Doyle Lawson and Quicksilver where he played on the making of two albums, 'Sing Me A Song About Jesus' and 'Drive Time'.
Jessie then joined Dailey & Vincent in April 2012 and has played on the band's album(s), 'Brothers of the Highway' , 'Alive!