Rock starred in his first HBO comedy special in 1994 titled Big Ass Jokes. But it was his second stand-up special, 1996’s Bring the Pain, that reinvented Rock as one of the best comedians in the industry. For it Rock won two Emmy Awards and gained large critical acclaim. The segment on race in America, in which Rock used the “N word” extensively was most talked about.
Rock later had two more HBO comedy specials: Bigger & Blacker in 1999, and Never Scared in 2004. Articles relating to both specials called Rock “the funniest man in America” in Time and Entertainment Weekly.
Rock's fifth HBO special, Kill the Messenger, premiered on September 27, 2008, and won him another Emmy for outstanding writing for a variety or music program.