Who is the funniest CEO?

The pick: Herb Kelleher

Co-founder and longtime CEO of Southwest Airlines, died 2019

The CEO most often profiled for his humor, by D Magazine, Fortune, the Boston Globe and Southwest's own history.

Also in the running

• Richard Branson (Founder of the Virgin Group): Known for public stunts; Business Traveller covered him working an AirAsia flight dressed as a flight attendant after losing a Formula 1 bet with AirAsia's CEO.
• Michael H. Jordan (Chairman and CEO of EDS, died 2010): Named by D CEO magazine as an executive known for spontaneous one-liners, such as joking that EDS once had more presidents than the UN.

What made them funny

Kelleher's humor was a performance, and he gave it a stage. D Magazine describes him dressing as a referee to call penalties on competitors in commercials and doing what it calls notoriously bad Elvis impersonations. Fortune notes that Southwest's headquarters still has a life-sized cutout of him as Elvis and a button that plays his laugh in three increasingly loud versions.

Underneath the costumes, most of his jokes pointed at himself. He opened a university lecture by thanking the audience for lowering their standards, and Southwest's own history credits him with a balance of self-deprecating humor and sheer brilliance. A CEO who mocks himself first makes it safe for everyone else to laugh, which is part of why the jokes spread from the boardroom to the baggage handlers.

Techniques to take into your videos and sets

1. 1. Settle the fight with a show

   What they did

   In 1992 another aviation company, Stevens Aviation, said Southwest's "Just Plane Smart" slogan was too close to its own. Instead of going to court, the two CEOs held a public arm-wrestling match for the rights, billed as Malice in Dallas. Kelleher trained publicly, entered in a white bathrobe as "Smokin' Herb," and lost. Stevens let Southwest keep the slogan anyway.

   Why it works

   Everyone expects a dispute to be settled with lawyers and paperwork. Swapping in a sports event, complete with a nickname, a robe and a training montage, makes the stakes absurd and turns both sides into characters the audience roots for.

   Example (original, written by Shutap)

   My roommate and I are settling who left the frying pan in the sink for three days with a best-of-five Mario Kart tournament. Weigh-ins are at 7. The pan will be ringside.

   Try it

   Take a small argument from your life and stage it as a title fight: give each side a nickname, a venue and one ridiculous piece of gear.

2. 2. Thank them for lowering their standards

   What they did

   D Magazine reports Kelleher opening a lecture at Southern Methodist University with "Thank you for lowering your standards to have me here tonight." The first line out of his mouth lowered his own status before anyone else could.

   Why it works

   An audience braced for a powerful speaker relaxes when he hands them the first laugh at his own expense. It also defuses anyone waiting to knock him down, because he already did it.

   Example (original, written by Shutap)

   Huge thanks to the 38 people who watched my last video to the end, and a special shout-out to the four of you who did it on purpose.

   Try it

   Open your next video by thanking the audience for something that makes you look smaller, with one exact number in it.

3. 3. Inflate a small win to world scale

   What they did

   When a long-running local fight over flight limits at Dallas Love Field ended in a deal, D CEO quotes Kelleher's reaction: "There's hope for world peace." A regional airport agreement, treated as a breakthrough for humanity.

   Why it works

   Grand language on a small event is mock-epic, and the gap between the size of the words and the size of the thing is the joke. It also tells the audience exactly how long and tiring the fight was without listing a single detail.

   Example (original, written by Shutap)

   My landlord fixed the dryer in under three weeks. If he can do it, I believe the UN can do anything.

   Try it

   Find the most dragged-out small fight in your week and announce its ending like a historic treaty.

4. 4. Wear the joke they're making about you

   What they did

   Fortune recounts that Kelleher posed in a Southwest ad with a bag over his head and jokingly offered the bags to customers. Rather than argue with an embarrassing picture, he became it.

   Why it works

   Acting out the insult takes its power away: no one can mock you harder than you just mocked yourself. A visual prop makes it land instantly, even with the sound off.

   Example (original, written by Shutap)

   Comments said my apartment tour was depressing, so this week every guest gets a tissue at the door, folded into a little swan by me.

   Try it

   Take the most common jab in your comments and turn it into a prop you hold up on camera.

Before you quote them

No poll or published ranking names a funniest CEO, so this pick rests on how often Kelleher is profiled for his humor, not on a vote. Warren Buffett, also a longtime CEO, is covered on the funniest billionaire page. Many one-liners credited to Kelleher online can't be traced to a source; the quotes above come from D Magazine, D CEO and Southwest's own account of the 1992 match.

Questions people ask

Who is the funniest CEO?

Herb Kelleher, co-founder and longtime CEO of Southwest Airlines, is the one most often profiled for his humor. No poll ranks CEOs by funniness, but D Magazine reported in 1996 that he'd been called the clown prince of the airline industry, and Fortune's 2019 tribute called him a clown with a spine of steel.

What was the Malice in Dallas?

A 1992 arm-wrestling match between Kelleher and Kurt Herwald of Stevens Aviation over the slogan "Just Plane Smart." Kelleher entered in a white bathrobe as Smokin' Herb and lost to "Killer Kurt," who then let Southwest keep the slogan, according to Southwest's own account.

What is Herb Kelleher's funniest line?

One of the best documented is how he opened a lecture at Southern Methodist University, as D Magazine reported: "Thank you for lowering your standards to have me here tonight." When the Dallas Love Field fight ended in a deal, D CEO quotes him: "There's hope for world peace."

Which other CEOs are known for being funny?

Richard Branson of the Virgin Group, whom Business Traveller showed working an AirAsia flight dressed as a flight attendant after losing a Formula 1 bet, and Michael H. Jordan of EDS, named by D CEO in 2006 for spontaneous one-liners such as EDS once having more presidents than the UN.

Sources

• D Magazine, August 1, 1996: D Magazine (1996): Herb Kelleher has more fun than you do
• D CEO, September 1, 2006: D CEO (2006): Laugh it up (Kelleher, Michael Jordan of EDS)
• Fortune, January 16, 2019: Fortune: Remembering Herb Kelleher
• The Boston Globe, January 3, 2019: Boston Globe: Herb Kelleher, co-founder of Southwest Airlines, dies at 87
• Southwest Airlines, accessed October 20, 2026: Southwest Airlines: Armed and dangerous, the Malice in Dallas
• Southwest Airlines, accessed October 20, 2026: Southwest Airlines history: About Herb
• Business Traveller, accessed October 20, 2026: Business Traveller: Branson dresses up as AirAsia stewardess