Having initially travelled to Britain at age 27as a serious theatre student (training at RADA), Hunter became a comedian after performing his first comedy set as a dare. For this set, he received £10. Realising he enjoyed it, and there was money in it, Hunter diverted his attention from his acting ambitions and re-focused on standup.
He often deals in his standup about issues regarding race that he feels important. Part of that is an attempt to reclaim the word "Nigga". He often uses the term in the titles of his shows, and - as a result - his show, Reginald D Hunter: Pride & Prejudice... & Niggas attracted some criticism and the poster was banned from the London Underground.
Hunter filled E4's 320-seater "Udderbelly" venue every one of 27 consecutive nights during the 2007 Edinburgh Fringe with his latest show, "Fuck You in the Age of Consequence" (the title being named as a response to the negative press reactions to his previous shows, "A Mystery Wrapped in a Nigga" and "Pride and Prejudice... and Niggas").