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15 Insights From the Ever-Hilarious Conan O’Brien

Conan O'Brien has been a renowned figure in the comedy world since he first graced television screens as a late-night talk show host in 1993. Born in Brookline, Massachusetts, he graduated as valedictorian from his high school in 1981 and went on to study at Harvard University. It was there that his comedy writing career began to take off, as he served as president of the school's Harvard Lampoon humor magazine. After graduating, O'Brien went on to write for Saturday Night Live and later The Simpsons, where he wrote fan-favorite episodes such as "Marge vs. the Monorail" and "Homer Goes to College."

In 1993, O'Brien was hand-selected by SNL creator Lorne Michaels as David Letterman's replacement to be host of NBC's Late Night. Alongside his sidekick, Andy Richter, he went on to establish a patented brand of zany humor that earned him a cult following. O’Brien hosted Late Night until he took over The Tonight Show from Jay Leno in 2009, though due to struggling ratings, NBC controversially stripped O'Brien of the role mere months later and gave the show back to Leno.

In the wake of the Tonight Show debacle, O'Brien proved his perseverance and thoughtfulness were on par with his natural humor. He began anew at TBS with a talk show called Conan, which earned praise for segments like "Conan Without Borders," in which the host traveled to countries such as Armenia and Cuba to explore their culture. Though he ended Conan in 2021, O'Brien now hosts an award-winning podcast called Conan O'Brien Needs a Friend, welcoming such prominent guests as Barack Obama, Bruce Springsteen, and Hillary Clinton.

Whether as a writer, host, or podcaster, O'Brien has always excelled at transforming the silliest of concepts into a beautifully executed joke. In having dealt with his own professional struggles, he has also been a source of insightful advice. The 15 quotes below are perfect examples of this comedy stalwart's intertwining views on humor and life.

Nobody in life gets exactly what they thought they were going to get. But if you work really hard, and you’re kind, amazing things will happen.

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Whether you fear it or not, disappointment will come. The beauty is that through disappointment you can gain clarity, and with clarity comes conviction and true originality.

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My favorite comedy is comedy where nothing is achieved and there is no point.

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Fall down. Make a mess. Break something occasionally. But know that your mistakes are your own unique way of getting where you need to be and remember the story is never over.

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There are few things more liberating in this life than having your worst fear realized.

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Success is a lot like a bright white tuxedo. You feel terrific when you get it, but then you’re desperately afraid of getting it dirty, of spoiling it.

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When all else fails there's always delusion.

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Whatever you think your dream is now, it will probably change. And that’s OK.

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There's a mentality in show business where people will say, 'That was great! Do that all the time.' And you think, 'No.' By its nature the really great stuff has to be rare.

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Your path at 22 will not necessarily be your path at 32 or 42. One's dream is constantly evolving, rising, and falling, changing course.

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There's good random, and there's bad random. There's good silly, and there's bad silly, and you've gotta know the difference.

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Being a dad is the greatest, except for assembling things.

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Your perceived failure can become the catalyst for profound reinvention.

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People can like what I do or not like what I do, but Jesus, there's a body of work there, and I'm really proud of it.

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I just want to say to the kids out there watching — you can do anything you want in life. Unless Jay Leno wants to do it too.

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Featured image credit: Francis Specker/ Alamy Stock Photo

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About the Author
Bennett Kleinman
Bennett is a staff writer at Optimism as well as a freelance comedy writer. He's based in New York City.
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