Bobby Jackson graduated from Salisbury High School in 1992.  He attended Western Nebraska Community College and the University of Minnesota before being selected by the Seattle SuperSonics with the 23rd pick in the 1997 NBA Draft. As a Golden Gopher, Bobby Jackson led Minnesota to the Final Four, where they lost to the Kentucky Wildcats. He was traded to the Denver Nuggets prior to his rookie season where he played 68 games before moving on to a more familiar place in Minnesota where he donned a Timberwolves jersey for two seasons. He had his best years in Sacramento where he played for the Kings from 2000 to 2005 where he was known as "Action Jackson" and a crowd favorite. A former Sixth Man award winner, Jackson suffered an abdominal strain early in the 2004–05 season that forced him to miss 51 games.

On July 29, 2008, it was reported that Jackson would be traded by the Rockets back to the Sacramento Kings along with Donte Greene, a 2009 first round draft pick and cash consideration in exchange for Ron Artest (now Metta World Peace). The trade was completed on August 14, due to Greene's rookie contract signing on July 14.

Bobby Jackson retired on October 24, 2009.  He later became an assistant coach for the Sacramento Kings.

On June 5, 2013, new Kings coach Michael Malone announced that the 2012–13 assistant coaches would not be retained for the 2013–14 season.

On September 9, 2013, Jackson was hired by the Minnesota Timberwolves as a player development coach.