Christopher Matthew Tolbert was born on May 4, 1982, in McComb, Mississippi, and grew up in Woodville, Mississippi, about 45 minutes north of Baton Rouge. Tolbert attended high school at Centreville Academy, where he played football and track and field in addition to baseball. In 1998 and 1999, Tolbert's football team won back-to-back state football championships. During his senior season, Tolbert played running back and rushed for 2,561 yards on 326 carries. After graduation in 2000, Tolbert played baseball at the University of Mississippi in Oxford, Mississippi, for the Ole Miss Rebels. Tolbert spent his collegiate career playing shortstop and second base. He was named a Freshman All-American in 2002. The following season, Tolbert was drafted by the Baltimore Orioles, but did not sign with the team. In the 2004 Major League Baseball Draft, Tolbert was selected in the 16th round by the Minnesota Twins; he signed with the team on June 16, 2004.
Tolbert was selected by the Minnesota Twins in the 16th Round (481st overall) of the 2004 Major League Baseball Draft. Tolbert got his first major league hit on April 2, 2008, in the 3rd inning off Los Angeles Angels of Anaheim pitcher Joe Saunders. On April 11, 2008, Tolbert had his first career major league RBI against Kansas City Royals pitcher Gil Meche.
Following the Twins' 2009 spring training camp, Tolbert was optioned to the Triple-A Rochester Red Wings.
On May 6, 2009, Tolbert was called up from Rochester and became the starting second baseman.
Tolbert hit his first major league home run on May 21, 2009, against the Chicago White Sox's Jimmy Gobble. In the game, Tolbert went 3 for 6, scoring two runs and collecting 4 RBIs. Tolbert hit his second home run on September 22, 2009 against the Chicago White Sox's John Danks.
On October 20, 2011, he became a free agent.
On January 20, 2012, Tolbert signed with the Chicago Cubs to a minor league deal.
On February 6, 2013, Tolbert signed with the Philadelphia Phillies to a minor league deal.