Stephen Jesse Jackson wanted to play basketball from the time he was four years old. Many of Jackson’s relatives in Port Arthur, Texas, played on Lincoln High School State Championship teams. During his junior year in high school, Jackson led Lincoln High School to the State Championships. He was the high scorer and made All-American.
 
After graduation, Jackson went to play pickup basketball at the Phoenix Suns summer camp. Suns coach Danny Ainge saw Jackson's potential, and in 1997, Jackson was drafted but later waived by the Suns. Encouraged by Ainge to play overseas for more experience, Jackson played in Australia, Venezuela, and the Dominican Republic.
 
After playing overseas, the 200-pound, 6-foot-8 guard/forward was finally ready to try for the NBA again. He signed as a free agent with the New Jersey Nets in October of 2000 and joined the San Antonio Spurs in 2001. In 2003 Jackson scored 17 points for the San Antonio Spurs in the NBA championship game against the New Jersey Nets, winning the championship. In 2003, Jackson was a free agent with the Atlanta Hawks. Following the 2003-04 NBA season, the Hawks traded Jackson to the Indiana Pacers. On January 17, 2007, the Indiana Pacers traded Jackson to the Golden State Warriors. He also played for the Charlotte Bobcats and Milwaukee Bucks before returning to San Antonio in 2012. He retired from the Los Angeles Clippers on July 22, 2015.
 
Jackson has since pursued community center and school projects in California, where he resides. For several years, he also held a basketball camp for children in the Port Arthur area.

Jackson is currently host for the digital video podcast "All the Smoke with Matt Barnes and Stephen Jackson". The video podcast is available on Showtime Basketball's YouTube platform and other audio outlets such as iTunes and Spotify. The show has had guests such as Kevin Garnett, Snoop Dogg, Kevin Durant, Al Harrington, Shannon Sharpe, Chris Paul, Lil Wayne, Draymond Green, Deion Sanders, Steve Nash and Kobe Bryant. The podcast had the last exclusive interview with Kobe Bryant before he passed away.

Jackson was a close friend of George Floyd, who drew international attention when he was killed by police in Minneapolis on May 25, 2020. Jackson received media attention for an impassioned speech he gave at a protest rally in Minnesota. Jackson and Floyd called each other "Twin" due to their similar physical appearance.