Over the summer of 2018, Anderson signed a free agent contract with the Memphis Grizzlies after a successful four-year stint with the Spurs. He would find himself with more opportunities on a veteran-laden Memphis squad. The forward's first four months were successful, as he provided his usual well-rounded play. With Memphis, Anderson posted career-high per game averages in points (8.0), rebounds (5.8), assists (3.0) and minutes played (29.8). On New Year's Eve, Anderson put up a career-high-tying 20 points during a loss at Houston. On Nov. 10, the small forward grabbed a career-best 13 rebounds during a home win over the 76ers. Two nights later, he repeated the feat and snagged another 13 rebounds during a loss to the Jazz. On Jan. 4, Anderson dished a career-best-tying 10 assists versus the Nets. That contest would also mark his lone triple-double of the campaign, via 11 points, 11 boards and the 10 mentioned dimes. Unfortunately, Anderson's season ended prematurely as he began experiencing shoulder discomfort in early February and ultimately underwent season ending surgery.

With Kawhi Leonard missing all but nine games due to quadriceps issues, Anderson was thrust into the biggest role of his career during the 2017-18 campaign. He started 67 of 74 appearances, averaging career highs in points (7.9), rebounds (5.4), assists (2.7), steals (1.6) and field-goal percentage (52.7). He also set new single-game career marks of 20 points, 12 rebounds, 10 assists and four blocks. Arguably his best performance of the regular season occurred during a 20-point loss to the Warriors on Nov. 2. In 26 minutes, Anderson posted 16 points, seven rebounds, four assists, three blocks and a steal with just one turnover. Anderson's best stretch of the season was six games from Nov. 17-29. He averaged 11.8 points on 8.3 shots, plus 5.5 rebounds, 5.0 assists (1.8 turnovers) and 2.2 steals in 30.3 minutes. The Spurs finished the season 47-35 and lost to the Warriors in Round 1 of the playoffs. Anderson appeared in all five postseason contests, averaging 5.4 points, 2.6 rebounds and 1.2 steals in 14.6 minutes. He played his best playoff ball during the final two games of the series, averaging 10.0 points without missing a shot in addition to 3.5 rebounds and 2.0 combined steals-plus-blocks.

Anderson saw action in 72 games (14 starts) during the 2016-17 campaign. He received 14.2 minutes per game, averaging 3.4 points, 2.9 rebounds and 1.3 assists. He set career highs in three-point percentage (37.5) and free-throw percentage (78.9). Across Anderson's 14 starts, he averaged 5.6 points, 5.7 rebounds, 2.8 assists and 1.1 steals in 27.1 minutes. One of Anderson's best stretches of the season came in four games from Jan. 21-27, when he averaged 7.0 points, 4.0 rebounds, 2.5 assists, 1.5 steals and 1.5 blocks with just 0.8 turnovers in 25.5 minutes. His best overall game of the season occurred March 11 during a 22-point win over the Warriors. Anderson played 32 minutes and recorded 13 points, eight rebounds, six assists and one block with no turnovers. The Spurs finished the season 61-21, defeating the Grizzlies in the first round of the playoffs and the Rockets in Round 2 before losing to the Warriors in the Western Conference Finals. Anderson appeared in 15 playoff games (one start), averaging 5.5 points, 3.1 rebounds and 1.7 assists in 13.0 minutes. His best postseason performance came during the final game, which featured 20 points, seven rebounds, four steals and two assists over 27 minutes.

Anderson found a true rotational role with the Spurs during the 2015-16 campaign. He set career highs nearly across the board, appearing in 78 games (11 starts) while averaging 4.5 points, 3.1 rebounds and 1.6 assists in 16.0 minutes. He also set highs in field-goal percentage (46.8), three-point percentage (32.4) and free-throw percentage (74.7). In Anderson's 11 starts, he averaged 8.5 points, 4.6 rebounds, 2.5 assists and 1.9 steals across 28.9 minutes. He racked up new single-game career marks in rebounds (11), assists (seven), steals (five) and blocks (two). Arguably his best performance of the season occurred during a 96-91 victory over the Mavericks on April 13. He started, played 30 minutes and recorded 15 points, 10 rebounds, five steals, four assists and no turnovers. The Spurs finished 67-15, making the playoffs but losing in the second round to the Thunder following a sweep of the Grizzlies. Across 10 playoff appearances, Anderson averaged 2.3 points and 2.4 rebounds in 12.9 minutes. His best playoff performance came during the Game 1, 32-point win over the Thunder. He accumulated two points, seven rebounds, two assists, two steals and a block in 23 minutes of run.

Following two years of college ball at UCLA, Anderson was selected with the 30th overall pick by the Spurs during the 2014 NBA Draft. He made his NBA debut during the fourth game of the season Nov. 6 -- a 17-point loss to the Rockets. Anderson played 31 minutes off the bench and recorded four points, eight rebounds, four assists and two steals with no turnovers. Overall, he appeared in 33 games (eight starts), averaging 2.2 points and 2.2 rebounds in 10.8 minutes. In starts, Anderson averaged 5.0 points, 4.4 rebounds, 1.5 assists and 1.0 steals in 20.1 minutes. He set single-game highs of 15 points, nine rebounds, four assists, three steals and one block. Arguably his best all-around effort of the season came during a 109-95 win over the Knicks on Dec. 10. Anderson saw 23 minutes as a starter and posted nine points, five rebounds, three assists, two steals and no turnovers. The organization also opted to get Anderson some run in the D-League. There, he appeared in 26 games, averaging 21.3 points, 8.7 rebounds, 4.8 assists, 2.0 steals and 1.5 blocks across 40.1 minutes of run.