A native of Silver Spring, Maryland, Anderson was selected by the Red Sox in the tenth round of the 1985 amateur draft.

[4] Anderson hit his first major league home run on August 6, 1988 versus Milwaukee's Tom Filer at Memorial Stadium in Baltimore.

In only his first season as a full-time player in 1992, Anderson played in all but three of the Orioles games and led the major leagues with 749 plate appearances.

Despite missing 15 games with chicken pox and patellar tendinitis in both knees, Anderson led all American League leadoff hitters in extra-base hits (56) and RBI (62).

He hit two home runs on September 5, the night teammate Cal Ripken Jr. tied Lou Gehrig's consecutive games played record of 2,130.

On September 6, Anderson spoke on behalf of his teammates at a post-game ceremony honoring Ripken's 2,131st consecutive game.

In his first at-bat, he hit his 50th homer off Cy Young Award winner Pat Hentgen, breaking Frank Robinson's record for most home runs in a season by a Baltimore Oriole.

In the annual Baseball America "Tools of the Trade" poll, Anderson was named as the league's third-best defensive outfielder, behind only Seattle's Ken Griffey Jr. and Cleveland's Kenny Lofton.

Anderson also hit 37 doubles and five triples and led the American League in extra base hits with 92, breaking the Orioles club record previously held by Cal Ripken Jr. Anderson had more than doubled his previous best of 21 home runs in 1992, and his uncharacteristic power surge has since led to allegations that he used performance-enhancing drugs during the 1996 season.

[6][7][8] Despite playing most of the 1997 season with a broken rib, Anderson led the Orioles to a wire-to-wire American League East title with a record of 98-64.

In a post-season statistical analysis by Baseball America, Anderson was rated as the best leadoff hitter in the American League.

With one year remaining on a five-year contract, Anderson was released by the Orioles on November 16, 2001 after a season in which he batted .202 with eight home runs and 45 RBI in 131 games.

[12] He accepted an assignment to the Portland Beavers on March 27, 2003 after his attempt to make the Padres' Opening Day roster was not successful.

Louis Browns career statistics in:[15] He also holds the franchise's single-season record for total bases (369 in 1996) and times hit by pitch (24 in 1999).

Cal Ripken Jr. introduced Anderson and called him "the greatest lead-off hitter in Orioles baseball, and the best athlete I have ever played with.

[20] He left the organization at the conclusion of the 2019 season as a result of his role being significantly reduced after Mike Elias replaced Dan Duquette in charge of the team's baseball operations.

"[23] In 2020, Anderson began dating South Korean-American singer, actress and ballerina Stephanie, whom he met in Los Angeles in 2012.

[27] The trip took place November 8–16, 2011, and included visits to several towns (Tokyo, Ofunato, Nishinomiya, and Kyoto) affected by the 2011 Tōhoku earthquake and tsunami.