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. His routine, which featured commentaries on race in America, stirred up a great deal of controversy. Rock won two Emmy Awards for that special. Adding to his popularity was his much-publicized role as a commentator for Comedy Central's Politically Incorrect during the 1996 Presidential elections which earned him another Emmy nomination. Rock also was the voice for the "Lil Penny" puppet who was the alter ego to basketball star Penny Hardaway in a series of Nike shoe commercials from 1994--1998,and hosted the '97 MTV Video Music Awards.

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.

HBO also aired his talk show, The Chris Rock Show, which gained critical acclaim for Rock's interviews with celebrities and politicians. The show won an Emmy for writing. His television work has won him a total of three Emmy Awards and 15 nominations. By the end of the decade, Rock was established as one of the preeminent stand-up comedians and comic minds of his generation.

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