Pittman attended Mira Mesa Senior High School San Diego, California, and graduated in 1993. He was a first team All-Eastern League honoree. He played with older brother Wayne Pittman.
Pittman was selected in the 4th round of the 1998 NFL Draft (95th overall) by the Arizona Cardinals.
On January 26, 2003, Pittman played in Super Bowl XXXVII and rushed for 124 yards on 29 carries in Tampa Bay's 48-21 victory of the Oakland Raiders.
On November 7, 2004, Pittman scored on a 78-yard touchdown run against the Kansas City Chiefs, the longest run in Tampa Bay Buccaneers history.
On March 22, 2005, Pittman launched his official website, Pittman32.com, which has since gone offline. On September 11, 2005, the website was praised by Greg Auman of the St. Petersburg Times as "the team's best player site".
On January 7, 2006 during a Wild Card playoff game between the Buccaneers and Washington Redskins, Pittman was involved in an altercation with Redskins' safety Sean Taylor, who allegedly spat on him following a play. Pittman responded with a blow to Taylor's helmet. Taylor was ejected from the game that the Redskins won 17-10.
Pittman became a free agent following the 2007 season.
Pittman was placed on season-ending injured reserve with a neck injury. In eight games (three starts) during the 2008 season, Pittman rushed 76 times for 320 yards and four touchdowns.
On August 12, 2009, Pittman signed with the Florida Tuskers.
