Anderson attended Portsmouth Abbey School before he was expelled because of a campus incident. He transferred to Hope High School where he was a three-sport letterman. He received All-New England and All-Conference honors in football as a linebacker. He was an All-American in wrestling, winning the state and New England titles as a junior. He was also a good track and field athlete where he honed his running skills under the legendary Hope High School track coach Thom Spann. He also practiced the shot put. In 2001, he transferred to Avon Old Farms Prep.
In 2005, he lost his scholarship because of poor grades and off-the-field problems, which forced him to drop out of school. He returned in 2006 after a year out of football, under the condition that he would pay all of his college expenses, so he took out a loan with the help of an aunt and lived during a semester in an abandoned locker room on the campus, until he was able to gain back his scholarship. Although he was used mostly for blocking purposes in the offense as a senior, he received team MVP honors and was recognized as one of the best special teams players in the nation. He led his team in special teams tackles in each of his four years and only missed one game.
Anderson was selected in the sixth round of the 2007 NFL Draft, after the Dallas Cowboys traded up with the Cleveland Browns moving from the 200th to the 195th position, in exchange for a seventh round draft choice. He was expected to be a difference maker on special teams and was given the nickname "cricket" after eating an insect on a dare during training camp.
On September 17, 2008, he had his knee scoped and missed two games because of the injury. On August 13, 2009, he had surgery on his left knee, but did not miss any regular season games after returning on September 7 and finishing tied for fourth on the team with 12 special teams tackles.
Anderson was signed by the Miami Dolphins on October 19, 2010. He was placed on the injured reserve list with a triceps injury just 12 days after signing his contract. He was waived on March 3, 2011.
On June 1, 2013, Anderson won the Heavyweight Championship for the Real Cage Fighting Mixed Martial Arts (MMA) organization as well as the major food eating competition.
