53) Reggie Miller
Although Indiana Pacers legend Reggie Miller debuted in 1987, he was still going strong in the 2000s, or at least most of it. In the 1999–2000 season, Miller made his last all-star team by averaging 18.1 points while shooting 40.8% from three.
After being held back by playing in the same conference as Michael Jordan and the Chicago Bulls and several battles with the New York Knicks, the Pacers looked as though they might break through in 2000. Unfortunately, they went up against the Shaq and Kobe Lakers, who were a juggernaut that dispatched Miller and the Pacers in six games en route to the first of three championships.
Miller put up comparable numbers in 2000–01, but the Pacers failed to make it past the first round. After it became clear that he was in decline in 2001–02, following another first-round playoff exit, the Pacers retooled by focusing more on Jermaine O'Neal. He became a star, as did Metta World Piece, allowing Miller to take on less of an offensive role.
That resulted in Indiana winning 61 games in 2003–04 but coming up just short against the eventual champion Detroit Pistons. The following season, it seemed as though the Pacers would be far better after adding Stephen Jackson, who was coming off his best season, but the Malice at the Palace and injuries ruined their chances of another deep playoff run.
Miller would play one more season and still manage to put up nearly 15 points per game at 39. Overall, in 457 games from 1999–00 to 2004–05, Miller posted 15.2 points while hitting 37.9% of his threes. He also made an all-star team and was still one of the top shooters in the NBA. Although he failed to win a championship, his longevity makes him one of the best shooting guards in NBA history, and of the 2000s as well.