in 1991 jackson released "a guitar thing" at the age of 27, with collaborators including benny green, lonnie plaxico, and cecil brooks iii. this was his debut album as leader, and debuted at #26 on the r&r national airplay chart. he followed this up with the album "thinking of you", which he also released on muse records. in the early 1990s jackson fronted the ron jackson quartet. in 1995 jackson joined the group 5 guitars play mingus, playing alongside russell malone, leader peter leitch, david gilmore, and jack wilkins, in new york venues like the artscenter. he soon released an album of duets with rufus reid called "song for luis". in 1996 took first prize in the heritage international jazz guitar competition. as his career has progressed he has continued to work alternative music gigs such as subbing in orchestral pits, playing weddings and other parties, working in jam bands, and other positions. he was also a member of the rufus reid trio as well as the randy weston group. in 1999 jackson released the album "concrete jungle" with nicki parrott.