From there he went on to appear in other minor roles in many films including Any Given Sunday, 13 Moons and as the club doorman, in Cradle 2 the Grave. Speight has also appeared in many television shows such as Malcolm in the Middle, NYPD Blue, Arli$$, Prison Break and My Wife and Kids.
In 2003, Speight appeared in a Reebok commercial that aired during the Super Bowl. The role was based on a character that Speight had played in a short independent film in 2000. In the commercial, Speight plays Terry Tate, an office linebacker charged with the enforcement of office policies. For example, when one employee finishes the office's coffee and fails to begin brewing more, he is quickly tackled by Tate, who stands over the man, screaming "You kill the joe, you make some mo'!" Within the commercials, Speight promotes recycling, dutiful work, and several other courteous actions. The commercials received critical acclaim, and according to The Hollywood Reporter was the most watched part of the Super Bowl by TiVo viewers. The Office Linebacker spots recently returned as part of a campaign in support of voting. They feature several notable shorts of Terry Tate tackling a blind-sided Sarah Palin, leaving her moaning in pain on the ground. Tate emphasizes the importance of reading and providing lucid responses during media interviews.
Speight also had a recurring role on Damon Wayan's ABC series My Wife and Kids as Calvin Scott, the father of Vanessa Scott. For the 2006 Xbox 360 game Gears of War, Speight voiced the role of former "Thrashball" player Augustus Cole (a.k.a. Cole Train), humorously re-using some of his characteristic lines. He won the G-Phoria '07 award for Best Voiceover. Speight later reprised the role for Gears of War 2 in 2008, Gears of War 3 in 2011 and Gears of War: Judgement in 2013
Speight guest-starred as prison inmate Banks on the show Prison Break. Speight also had a role in the 2007 Eddie Murphy motion picture Norbit as Blue, one of the three brothers of Rasputia. He also appeared in Harold & Kumar Escape from Guantanamo Bay, as a character who is interrogated using racist methods. He then had a small role in the film Bachelor Party Vegas, as Gold Tooth, a prison rapist.
Speight appeared in an episode of ESPN's Mayne Street comedy short. In the 2008 TV film Ring of Death, Speight played convict "Milton Kennedy", a feared and revered gang boss (nicknamed "The President"), and undefeated champion of an underground fighting tournament in a notorious prison.
In 2009, Speight appeared in an episode of Bones, "Double Trouble in the Panhandle", which aired on the Fox Broadcasting Company. He played the Traveling Circus's strong man "Magnum".