Caught on Camera: The 15 Funniest Business Moments Ever

Business leaders’ crowning moments aren’t limited to their financial accomplishments. Instead, many have to do with their bloopers, missteps, and comedic skills. Here are the 15 funniest business moments ever, caught on camera for your viewing pleasure:

15. Jeff Bezos on the Daily Show

Jeff Bezos laughs freakishly hard during his appearance on the Daily Show.

14. Trump vs. Rosie

“We’re all a little chubby…”

13. The New Face of American Airlines?

Kevin Spacey makes some hilarious comments about absentee Bold in Business Award winner Ryanair.

12. Zappos CEO gets B*tch Slapped

In a weird exercise of team building and heavy drinking, CEO Tony Hsieh gets an employee to slap him across the mug. Don’t worry, he’s okay; he hit the self-described redneck next to him right after. Must be a marketing thing!

11. Carly Fiorina’s Punditry

Carly Fiorina, the former CEO of HP, comments on her new bosses’ inexperience–and shows her true colors.

10. Sponsor a CEO

For less than the cost of 1,000 lattes a day, you too can help an executive in need.

9. Erin Burnett Travels too Much

A jet-lagged Burnett has no filter on the Morning Joe show, leading her to comment about a “monkey in the middle.”

8. Jon Stewart vs. CNBC/Jim Cramer

The Daily Show With Jon Stewart M – Th 11p / 10c
Jim Cramer Battle
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Economic Crisis First 100 Days

Jon Stewart’s series of hilarious jabs at CNBC culminated in a sober face-off with Jim Cramer. Though the Cramer segment is serious, Stewart’s CNBC jokes are anything but.

7. Sue Herrera Says the C-Word

10 Times Movies Depicted Big Businesses As The Villain

Notice the S&P is riding at about 1372 and the news is about an amazing surge in the Nasdaq, must be a classic!

6. Bloomberg Reporter Cusses

Ever wonder why Bloomberg Financial Television always lags in the ratings? Here’s one possible answer.

5. Jim Cramer: “They Know Nothing!”

Not so funny if your 401K was heavy into Bear Sterns, but otherwise, this segment was hilarious. The magic moment comes at 2:32 into the video.

4. Charlie Gasparino is Just Like You

Anyone who has ever met Donnie Deutsch in person should be absolutely floored that it wasn’t him who dropped the F-bomb.

3. Bill Gets Gets a Facial

This whipped cream pie lacked the Service Pack 3 upgrade and was found to be in opposition of anti-trust laws in Brussels.

2. Steve Ballmer Loves Miami Sound Machine

I bet your entire market share that Steve Jobs would never do this. He would have used U2 at the very least!

1. Steve Wozniak in Footloose

Founder of Apple and perennial goofster-geek Steve Wozniak can actually dance…just not well. Known as “the other Steve” and “Wonderful Wizard of Woz,” he continues to charm in this viral video.

Written by Drea Knufken

Drea Knufken

Currently, I create and execute content- and PR strategies for clients, including thought leadership and messaging. I also ghostwrite and produce press releases, white papers, case studies and other collateral.