Chris Rock

February 24, 1997
In his first Oprah Show appearance, Chris didn't get top billing. Instead, Oprah first interviewed Li'l Penny, the popular pint-size puppet—voiced by Chris—who appeared in NBA star Anfernee "Penny" Hardaway's Nike commercials.

When Chris finally did get his proper introduction, he delivered some of the outrageous jokes that earned his second album, Roll with the New, a Grammy in 1998. "Do people owe you money and still have the nerve to buy clothes around you? Like, 'Hey, look what I just picked up?'" he said. "Did you see my money while you were down there?"
Chris Rock and Oprah

September 25, 1997 
By the time Chris returned to The Oprah Show in September 1997, he was no longer a cult comedian—he was on top of the world! He'd won a couple of Emmys, was regularly featured on magazine covers and called "the funniest man in America," and he was about to release the book Rock This!. Oprah told Chris his book was so hilarious she'd been calling Gayle at night to read her the funniest passages.

"One of the saddest sights in the whole world is a black woman with a credit card. Credit card coming all shaking. They start ringing it up and what does the black woman start doing? Crossing her fingers, 'Oh, Lord. Oh, Lord, please let it go through. Don't embarrass me in front of all these white people today. Oh, Lord, Lord, Lord,'" Chris joked. "They invented layaway for black people. A brother will layaway a house if they let him."

This moment was chosen as one of The Oprah Show's top 5 Chris Rock moments. Watch all five now!
Chris Rock

February 08, 2001
When he came on The Oprah Show shortly after President George W. Bush's 2001 inauguration, Chris had politics on his mind. "You made Bush win," Chris joked to Oprah. "Hey, I'm not blaming; I'm just saying. And you know you did it too. And you and Gore kind of hit it off."

"He liked my boots," Oprah said.

"He liked more than your boots. I saw the eyes," Chris said. "I met Clinton. He is a charmer. I would have slept with him. I was almost there. I had to pull back. I was like, 'I'm married. I'm married.'"
Oprah and Chris Rock via satellite

May 13, 2002
In May 2002, Chris broke the news that he and his wife, Malaak, had just learned that their first child was going to be a girl. And was Chris ever relieved! "I would have been too hard on a boy," Chris joked. "I would have been smacking a boy upside the head every day. 'Boy, you know how the white man's gonna treat you? Come on, get up, it's 4 in the morning. Go to work.' 'I'm only 4, Dad.'"
Chris Rock and Oprah

March 19, 2003
In 2003, Chris' directorial debut, Head of State, told the unlikely story of an unknown African-American legislator who comes out of nowhere to run for president. "You start looking around and I thought, 'I better write this movie, or you might run!'" Chris told Oprah.

The movie wasn't Chris' only big news that day. He had just become a father for the first time and had gotten a star on the Hollywood Walk of Fame. "I'm sure someone is stepping on it or spitting on it now," he joked.
Chris Rock's birthday greeting to Oprah

January 29, 2004
For Oprah's 50th birthday bash, several of her famous friends sent taped greetings, and Chris added his outlandish voice to the occasion. "I just want to say happy 30th birthday to Oprah Winfrey. You look great for 30. You wear it well. When they told me you were turning 30, I was like, 'Really?'" Chris joked. "How old is she? Fifty? Get the [bleep] out of here! She's not 50. Oprah is not 50. Kiss my [bleep]!"
Chris Rock

April 15, 2004
To promote his HBO comedy special Never Scared—later turned into a DVD and Grammy-winning CD—Chris had Oprah Show viewers in hysterics with his jokes about race and relationships. "Marriage is so tough Nelson Mandela got a divorce. He spent 27 years in a South African prison—beaten and tortured, made to eat horrible food for 27 years," Chris joked. "He spent six months with his wife and said, 'I can't take it!'"

This moment was chosen as one of The Oprah Show's top 5 Chris Rock moments. Watch all five now!
Chris Rock and Oprah

February 28, 2005
At Oprah's After-Oscar® Party in 2005, Chris—who hosted that year's Academy Awards—revealed how he gets himself psyched up for the biggest performances of his life. "I yell at myself. I come out of my body and start smacking myself. 'Boy, you better go out there and do that!'" he said. "I become my dad."
Chris Rock on location in Houston

September 07, 2005
When Hurricane Katrina and Hurricane Rita slammed the Gulf Coast, it was no time for laughter. Instead, Chris joined the Angel Network team in Texas, helping the Houston Food Bank deliver much-needed aid to residents. He even loaded up a truck with supplies and went in search of families who desperately needed food. "It feels really good to be out here and to be contributing," Chris said. "It's black and white, Mexican and Asian—everybody's out here together—helping to help people. This is incredible."

When Chris met one little girl in a shelter, he told Oprah he was reminded of his own daughters. "I said, 'Who are you with?' And she's like, 'My daddy.' To her, nothing was going to go wrong as long as she had her daddy," Chris said. "You think you've got all this other stuff, but all you've got is family. I think this experience will affect me for the rest of my life."
Chris Rock and Oprah

September 22, 2005
In September 2005, Hollywood was buzzing about the sitcom Everybody Hates Chris, based on Chris' Brooklyn childhood. Before talking about creating and producing the show, Chris had a few things to say about The Oprah Show's newly renovated set. "There's no couch!" he joked. "What's Tom Cruise going to stand on?"
Chris Rock with his family and Oprah

February 28, 2007
For his 2007 movie I Think I Love My Wife, a remake of the 1972 French comedy Chloe in the Afternoon, Chris revealed how he added details from his own life to the film. "Like watching The Wiggles on TV," he said. "And checking to see if there's any black kids at the play dates."
Chris Rock on African American Lives 2

January 23, 2008
In one episode of Dr. Henry Louis Gates Jr.'s groundbreaking PBS series African American Lives 2, Chris learned about his roots. On the show, Dr. Gates revealed that Chris' great-great-grandfather, Julius Caesar Tinghman, had served as a corporal in the U.S. Colored Troops during the Civil War. By the time he died in 1917, Julius had gone from being a slave with no possessions to owning 65.5 acres of land.

Chris told Oprah his experience with Dr. Gates was unbelievable. "Even while it was going on, he was telling me, 'Your great-great-grandfather owned property,' and 'Your great-great-grandfather did all this stuff.' I thought I was being punk'd. I really did," Chris joked. "I thought Ashton Kutcher was going to come from behind something and go, 'You know your grandfather was nothing but a slave. You know he just mopped up for white people. Come on, we got you.'"
Chris Rock

October 10, 2008
In 2008, Chris brought Ben Stiller, his co-star from the animated Madagascar movies, to The Oprah Show. In the children's movies, Ben is the voice of Alex, a lion born in the Central Park Zoo, and Chris is the voice of Marty, a zebra with a signature catchphrase—"crackalackin."

"My kids—especially my youngest—she likes to brag that her dad is the zebra from Madagascar," Chris said. "So any time there's a birthday party, I have to say 'crackalackin' all day."
Chris Rock feels Oprah's hair

September 30, 2009
For his acclaimed 2009 documentary Good Hair, Chris traveled from beauty shops in Brooklyn to sacred Indian temples to get to the root of why African-American women place so much importance on their hair. Chris even confronted Oprah about her locks. "You've got your hair nice today, though. You knew this was the hair show," he said. "You got a little extra piece here, though."

"I do not. No extra pieces," Oprah said. "All mine."

Watch Chris feel Oprah's hair!

Chris Rock

October 09, 2009
Several days after Chris first discussed Good Hair on The Oprah Show, he was back to defend himself against his critics. Some viewers thought Chris had revealed too many secrets about African-American hair, and they feared he had made black women into a punch line.

"My first intent is always to make people laugh, but at the same time, put a little Oprah in there. Put a little information in there ... a little positivity," Chris said. "It's not important what's on top of your head—it's important what's inside of your head. That is the theme of the movie."
Chris Rock and Oprah

Photo: George Burns/Harpo Studios

April 22, 2011
For his Oprah Show farewell—his 26th appearance—Chris was his usual hilarious self, taking on everything from his own Broadway debut to Charlie Sheen and Donald Trump.

But Chris knew he was many years removed from that fresh-faced comedian telling jokes on The Oprah Show in 1997. "I'm not old old, but I'm 46. You know what 46 means?" Chris jokes. "The only time I will ever be referred to as young is if I die at 46. 'He was so young. I can't believe it. He was just here on the show.'"