Chapman was the first draft pick of the expansion Charlotte Hornets and played on four National Basketball Association (NBA) teams.

After retiring, Chapman held several jobs with NBA teams, culminating in being the vice president of player personnel with the Denver Nuggets.

[1] Rex's father is Wayne Chapman, who played in the American Basketball Association and coached Kentucky Wesleyan College to two NCAA Division II national championships.

[2] Chapman had a turbulent relationship with his father; he and his sister, Jenny, "used to pray that Wayne's teams would win" so the mood of the house would not be tense, while his mother, Laura, would attempt to defuse the tension.

[3] In 2020, radio host Matt Jones described Chapman as, "the biggest high school basketball player that ever came from the state.

[4]: 5:12–5:22  Chapman, joined by teammates such as future NBA journeyman Winston Bennett, helped lead Kentucky to the SEC title[a] with a 27–6 record.

[7] Kentucky reached the Sweet Sixteen, where Chapman scored a career best 30 points in a losing effort against Villanova.

[6] Chapman was named to the All-SEC Team both of his college years and amassed a total of 1,073 points before opting to enter the NBA draft.

[2] The Bullets traded Chapman, with Terrence Rencher, to the Miami Heat for Ed Stokes and Jeff Webster in June 1995.

In Game 1, he set a play-off record for three-point shots (nine),[14] which was surpassed by Klay Thompson (11) in 2016 and Damian Lillard (12, 2OT) in 2021.

After the surgery, he was prescribed OxyContin, which increased his drug dependency, in part because it also helped ease the social anxiety he felt.

[10] Danny Ainge, who coached Chapman with the Phoenix Suns and became a close friend, said "Rex was a great competitor.

[2] Urged by Ainge to enter rehab for his drug problem, Chapman was diagnosed with attention deficit disorder and depression, for which he was medicated.

[2] In 2006, Chapman accepted the position of vice president of player personnel with the Denver Nuggets, which he held for four years.

[4]: 12:16–12:20 [19] Returning to the store several times, he was eventually identified by multiple employees based on his tenure in the NBA.

[2] Following his time in Louisville, Chapman continued to seek treatment in Texas and was hired by TNT to broadcast Kentucky's 2015 Final Four Game.

[20] Chapman eventually moved back to Lexington, where he states he stays clean, eats healthily, and swims daily.

[5] After previously declining any kind of sponsorship, during the COVID-19 pandemic Chapman was able to raise more than $150,000 to support those experiencing financial hardship.

[21] Since 2019, Chapman has been the television presenter of a Block or Charge show which appeared on Adult Swim, based on his tweets.

[22][23] He also hosts a podcast called The Rex Chapman Show, which debuted on Basketballnews.com on March 16, 2021, with friend and actor Josh Hopkins.

[27] In February 2024, Chapman's "blunt memoir about stardom, addiction, and American culture" It's Hard For Me To Live With Me was published.