He was widely known for his clutch hits, and writers for publications including The New York Times and Newsday had referred to him as one of the best pinch-hitters in the game.

As a senior, he posted a .357 batting average with thirteen home runs, and was the Sun Belt Conference Player of the Year and a Baseball America first team All-American.

On September 8 of the same year, he made his Major League debut as a pinch hitter, hitting a home run off Mel Rojas of the New York Mets.

The ball caromed away from center fielder Steve Finley, who ran it down in right-center field as Anderson circled the bases.

On August 31, 2006, Anderson was traded by the Nationals to the Los Angeles Dodgers after scoring the winning run in a 6-5 thriller against the Phillies in Washington.

He was intended to be a pinch hitter, but Anderson won the starting job in left field when rookie Andre Ethier struggled towards the end of the season.

On September 18, 2006, with the Dodgers playing the San Diego Padres for first place in the National League West with only two weeks left in the regular season, Anderson went five for five, including two home runs.

The Dodgers would eventually win the game on a walk-off home run by Nomar Garciaparra, and would tie San Diego for the NL West title.

On August 29, 2007, Anderson was part of a controversial call between the Mets and second-place Philadelphia Phillies at a game at Citizens Bank Park.

With the Phillies leading 6-5 with one out and the bases loaded in the ninth inning, Shawn Green hit a high-chop ground ball to shortstop.

Anderson served as a hitting coach with the Hagerstown Suns in 2011 and 2012 and was hired to fill the same position with the Brooklyn Cyclones in 2018.