Anderson was born July 18, 1974 in Louisville, Kentucky. He was a graduate of Doss High School and was a All-Star in the state of Kentucky. Anderson played college basketball at the Ohio State University and the University of Kentucky. In 1996, Anderson helped the University of Kentucky win the NCAA Men's Basketball Championship as part of a team that featured nine future NBA players under their coach Rick Pitino. Anderson went on to graduate from the University of Kentucky in 1997 with a degree in pharmacy.
He was first selected by the Cleveland Cavaliers as the 13th overall pick to the 1997 NBA draft, despite missing much of his second senior season at Kentucky due to a torn anterior cruciate ligament (ACL). He played for Cleveland from 1997 to 1999. On August 4, 1999 he was traded by the Cleveland Cavaliers along with Johnny Newman to the L.A. Clippers for Lamond Murray. Anderson was ranked 7th in the NBA in free throw percentage (.877) in 1999–2000.
Anderson's NBA career was plagued by injuries. In the 2004–2005 season he only played in 8 of the final 42 games for the Portland Trail Blazers, and missed similar numbers of games in prior seasons. On August 3, 2005, he was the first player in the league waived using the so-called "luxury tax amnesty clause" of the 2005 NBA collective bargaining agreement. He would sign with the Houston Rockets as a free agent before being traded to the Miami Heat in exchange for Gerald Fitch. The Heat would win the 2006 NBA Finals in six games after defeating the Dallas Mavericks to give Anderson his first championship.
Anderson was waived by Heat on September 12, 2006, prior to the beginning of the 2006–07 season. Several weeks later, on November 28, he signed with the Charlotte Bobcats; Anderson played the final two seasons of his career for the Bobcats.