Crawford attended Pattonville High School in Maryland Heights, Missouri, where he graduated in 1986.
As a child, Crawford suffered from numerous hardships, including a struggle with weight, a near-drowning at age 10, and abandonment by his father (Daryl Crawford), a body builder. However, according to his 2011 DVD of the October 23, 2010 "Can a Brother Get Some Love?" show at the Roberts Orpheum Theater in St. Louis, MO, the two have reconnected.
Crawford also appeared on AMCís Breaking Bad with the recurring role as Huell Babineaux, Saul Goodmanís bodyguard, and on Itís Always Sunny in Philadelphia as a standup comedian going by the stage name Landslide. He also appeared in an episode of Tosh.0, where he helps "the worst stand up comedian" redeem himself. Crawford also has a small supporting role in the Lionsgate film American Ultra, starring Jesse Eisenberg and Kristen Stewart, which hits theaters in 2015.