Chris Rock's Farewell Appearance

Chris Rock is a busy man. Over the course of his career, he has sold out record-setting comedy tours, won multiple Emmys® and Grammys®, hosted the Oscars®, appeared in a whopping 26 movies and is now debuting in a Broadway play. But through it all, he has always found time to visit Oprah. In fact, today is the 26th time the comedian has been on The Oprah Show, making him the second most frequent celebrity guest after Celine Dion!

Watch Chris' all-time best jokes on The Oprah Show

Chris made his Oprah Show debut in 1997, and 14 years later, he's still one of Oprah's all-time favorite guests and always has her laughing. "I could see even back then that he had a special gift," Oprah says. "I just love the way his mind works."

Whenever Chris stops by, Oprah says she knows she's not only going to laugh but also look at things just a bit differently.

"I always try to find the part of a topic that I can be original about," Chris says. "It's not like, how can I make it funny? It's just, how can I talk about that thing? … I'll sit on something for a while until I figure out what's my angle to that story."

Watch Chris take on the names in the headlines

While making people laugh is his primary goal, Chris says he also wants some people to be uncomfortable. "Sometimes my wife is like, 'I can't believe you're going to say that.' I'm like, 'I'm saying the exact right thing right now,'" he says.

When he's not sure about a bit, Chris says he just tries to talk about what intrigues him most. "If I'm interested, then I can be real passionate about it and it's not a job," he says.

These days, Chris is stepping out of his box and into something completely new: Broadway. His new show, The Motherf**ker with the Hat, is being called the most explosive play on Broadway. The play is about an addict just out of jail, played by Bobby Cannavale, and his irresponsible AA mentor, played by Chris.

Chris says working on this play has taught him that there is still more to conquer. "You get to a point where you think, 'I've done just about everything,'" he says. "I've been blessed to have this career. I've been blessed to have this forum, and I should take complete advantage of it. Try everything, and if you don't like something, you don't like it because you tried it, not because you dismissed it."

You're never too old to try something different, Chris says. "Your life can always be new."

Chris says his path to Broadway started when he saw the 2010 revival of August Wilson's play Fences, starring Denzel Washington and Viola Davis. "When you watch Denzel, it's like watching Moses. It's like watching Spider-Man—a real, live superhero in an unbelievable feat. He moved me," Chris says. "At that moment, I told the producer Scott Rudin, 'If you find me a script, I will do it. I really want to do it. I want to be involved in an ensemble; I don't want it to just be about me. I want it to be about the play and the work.' And they gave me this script, and I read it, and I was like, 'Wow, I'll do that one.'"

Though he's been in 26 films, Chris says being on stage is completely different than acting for the screen. "The level of preparation alone, it's like I've been in no films compared to this," he says. "Think about your favorite book. ... Could you recite it? Imagine knowing something that detailed to the point you could recite it and play with it and do it fast and do it slow. And be it."

Watch Chris give a backstage tour at The Motherf**ker with the Hat

When Oprah reveals to Chris that she's always wanted to act on Broadway, Chris tells her to go for it. "You're going to grow as an actress because you're going to play with these emotions. You're going to do it in so many different ways. Almost every night, you're going to be another person," he says. "Please, I want you to do it. You'll be a different person. I hope I'm in it—I'll do it."

Chris has been married to his wife, Malaak, for nearly 15 years, and they have two daughters, Lola, 9, and Zahra, 7. As a proud father, Chris says he has just one job: "Keep my daughters off the pole. That's it! No stripper daughters," he says. "Not that there's anything wrong with it, but it's wrong for my daughters."

When Oprah asks Chris to give himself a grade as a father, he declines. "It's the one job where you have to put 25 years in before you get your grade—you don't get midterms," he says. "Many a father or mother started off great, and then something happened and they fell off. Parenthood is a journey. It's a marathon. You don't get points for doing half the marathon."

Watch Chris tell a story about girls and boys today

Chris says he's only having more fun as his daughters get older. "I think I'm getting better. I'm younger than the other parents, or younger acting anyway," he says. "I thought I was having fun when they were 3, now they're 9 and 7—fun! Now they can talk, and they've got opinions.."

Despite now qualifying as one of the elder statesmen of stand-up, Chris says no topic is off limits for his comedy. "I mean, you don't want to hurt people...unless they've hurt people. But I'll talk about anything and find the angle into it," he says.

One thing that has changed is that instead of being an up-and-coming talent, Chris now gets asked for advice from younger comics. "(a) When I meet you in Detroit or Cincinnati, move. Not that there's anything wrong with those towns, but show business is in New York and Los Angeles and Oprah in Chicago," he says. "(b) You have to be a student of comedy. You have to do it because you want to do it; don't do it because you want to get famous. It's too easy to get famous. ... People think, 'Cameras should follow me because I've got a personality.' Everybody's got a personality. What is your backbone? Are you trained as an actor? Are you trained as a journalist?"

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