• Home
  • Latest
  • Fortune 500
  • Finance
  • Tech
  • Leadership
  • Lifestyle
  • Rankings
  • Multimedia
SuccessJon Stewart

Jon Stewart says David Letterman gave him the best career advice after his first talk show was canceled: ‘Don’t confuse cancellation with failure’

By
Chloe Berger
Chloe Berger
Down Arrow Button Icon
May 22, 2024, 2:56 PM ET
David Letterman once imparted some of Jon Stewart's greatest advice.
David Letterman once imparted some of Jon Stewart's greatest advice.SAUL LOEB / Stringer—Getty Images

Most of us have been pushed and landed on our ass, instead of our feet, at one point or another. Of course, being callously told to throw your stuff in a cardboard box and leave lends itself to feelings of humiliation. But just because someone fires you doesn’t mean it’s the end of the road, at least if you take fellow late-night icon Dave Letterman’s advice to Jon Stewart to heart.

Recommended Video

“They have locked the door and told me, ‘Get your shit and get out’,” Stewart told fellow comedian Larry Wilmore in 2016 during the final episode of Wilmore’s canceled late-night talk show, The Nightly Show. Stewart was talking about how some people in the entertainment world treated him after missteps in his early career. Back in the early 1990s, Stewart had a talk show of his own on MTV, aptly titled The Jon Stewart Show. He described it as a bit of a scramble as the show was bought by Paramount to replace comedian Arsenio Hall’s. 

“I was the natural replacement for Arsenio. Because I think a lot of people are like, ‘Hey, the hip African American guy, let’s stick a maybe small Jew in his place and see what happens,’” Stewart said sarcastically on a recent Q&A at The Daily Show.

The Jon Stewart Show shuttered after less than a year. “We were all very sad,” Stewart said, explaining that “when your name is on it and they tell you to get out of the building, it’s very hurtful.” And nine months after its first airing, Letterman came onto Stewart’s last show to impart some wry words of wisdom. 

“He said to me: ‘Don’t confuse cancellation with failure,’” Stewart said. 

“I thought that was really interesting,” Stewart continued. “Then in the commercial break, he said, ‘Although… this is also a failure.’ He just didn’t want me to confuse it,” he joked. And Letterman was largely right. While the MTV gig itself might have not been a success, Stewart went on to reinvent the late-night comedy scene with a new form of political satire and commentary for decades at Comedy Central’s The Daily Show. His defeat didn’t mean the end of his career.` 

Stewart imparted Letterman’s words to Wilmore when the latter was experiencing his own cancellation. “I took that to heart,” he said of Letterman’s quip, at the time.

Of course, not many of us are in the entertainment industry, so a one-to-one application of Letterman’s advice might be a little unhelpful. But the larger sentiment rings true as people, especially in the tech and media sector, experience layoffs. What might feel like the end of the road could amount to just a blip in it—much like the classic phrase from baseball player Yogi Berra, “It ain’t over.” 

Right now, the job market feels especially trying as even recruiters admit the process is arduous and long. But just because a boss has ushered you out the door, like Stewart, it doesn’t mean there aren’t greater things ahead. There’s always room to pivot for a better fit. 

“Regardless of your role at a tech company, your skills and expertise are valuable and can transfer to many other industries,” Sarah Doody, a future of work expert, told Forbes. “Just because your last job was at a tech company, that doesn’t mean you can’t get hired in another sector, and maybe even with a salary increase.”

Correction, May 22, 2024: An earlier version of this article misstated Larry Wilmore’s surname.

Join us at the Fortune Workplace Innovation Summit May 19–20, 2026, in Atlanta. The next era of workplace innovation is here—and the old playbook is being rewritten. At this exclusive, high-energy event, the world’s most innovative leaders will convene to explore how AI, humanity, and strategy converge to redefine, again, the future of work. Register now.
About the Author
By Chloe Berger
LinkedIn iconTwitter icon
See full bioRight Arrow Button Icon

Latest in Success

Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025

Most Popular

Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Rankings
  • 100 Best Companies
  • Fortune 500
  • Global 500
  • Fortune 500 Europe
  • Most Powerful Women
  • Future 50
  • World’s Most Admired Companies
  • See All Rankings
Sections
  • Finance
  • Leadership
  • Success
  • Tech
  • Asia
  • Europe
  • Environment
  • Fortune Crypto
  • Health
  • Retail
  • Lifestyle
  • Politics
  • Newsletters
  • Magazine
  • Features
  • Commentary
  • Mpw
  • CEO Initiative
  • Conferences
  • Personal Finance
  • Education
Customer Support
  • Frequently Asked Questions
  • Customer Service Portal
  • Privacy Policy
  • Terms Of Use
  • Single Issues For Purchase
  • International Print
Commercial Services
  • Advertising
  • Fortune Brand Studio
  • Fortune Analytics
  • Fortune Conferences
  • Business Development
About Us
  • About Us
  • Editorial Calendar
  • Press Center
  • Work At Fortune
  • Diversity And Inclusion
  • Terms And Conditions
  • Site Map

Latest in Success

Satya Nadella clasps his hands together and speaks in front of a lilac background on stage.
Successchief executive officer (CEO)
Satya Nadella called IQ without emotional intelligence a ‘waste.’ Research shows being vulnerable at work can even help CEOs win investor trust
By Sasha RogelbergDecember 16, 2025
19 hours ago
SpaceX CEO Elon Musk
SuccessBillionaires
Elon Musk’s wealth has soared past $600 billion—he’s now worth double the next richest person alive, Google’s cofounder Larry Page
By Emma BurleighDecember 16, 2025
19 hours ago
Photo of Reese Witherspoon
Arts & Entertainmentreese witherspoon
Reese Witherspoon says, ‘I don’t think my career would be possible’ in the age of AI and social media: ‘It’s a different world’
By Sydney LakeDecember 16, 2025
19 hours ago
Chris Kempczinski
SuccessCareers
As millions of Gen Zers face unemployment, McDonald’s CEO dishes out some tough love career advice for navigating the market: ‘You’ve got to make things happen for yourself’
By Preston ForeDecember 16, 2025
20 hours ago
TD Jakes
CommentaryReligion
To heal a divided nation, America’s next chapter must rediscover a common unity
By T.D. JakesDecember 16, 2025
22 hours ago
Little girl held in the arms of a man wearing a graduation cap and gown
Future of WorkEducation
The job market is so bad, people in their 40s are resorting to going back to school instead of looking for work
By Sydney LakeDecember 16, 2025
1 day ago

© 2025 Fortune Media IP Limited. All Rights Reserved. Use of this site constitutes acceptance of our Terms of Use and Privacy Policy | CA Notice at Collection and Privacy Notice | Do Not Sell/Share My Personal Information
FORTUNE is a trademark of Fortune Media IP Limited, registered in the U.S. and other countries. FORTUNE may receive compensation for some links to products and services on this website. Offers may be subject to change without notice.


Most Popular

placeholder alt text
Economy
America's $38 trillion national debt 'exacerbates generational imbalances' with Gen Z and millennials paying the price, warns think tank
By Eleanor PringleDecember 16, 2025
1 day ago
placeholder alt text
Success
Meetings are not work, says Southwest Airlines CEO—and he’s taking action, by blocking his calendar every afternoon from Wednesday to Friday 
By Preston ForeDecember 15, 2025
2 days ago
placeholder alt text
Success
'I had to take 60 meetings': Jeff Bezos says 'the hardest thing I've ever done' was raising the first million dollars of seed capital for Amazon
By Dave SmithDecember 15, 2025
2 days ago
placeholder alt text
Innovation
An MIT roboticist who cofounded bankrupt Roomba maker iRobot says Elon Musk's vision of humanoid robot assistants is 'pure fantasy thinking'
By Marco Quiroz-GutierrezDecember 16, 2025
22 hours ago
placeholder alt text
Future of Work
The job market is so bad, people in their 40s are resorting to going back to school instead of looking for work
By Sydney LakeDecember 16, 2025
1 day ago
placeholder alt text
Politics
Exclusive: After citations against Elon Musk’s Boring Company were suddenly withdrawn, federal regulators are now investigating Nevada OSHA
By Jessica MathewsDecember 16, 2025
12 hours ago