✈️ Trading Dignity for Decadence: The Things I’ll Do for a Private Jet
As a working stand-up comedian, I spend a significant portion of my life in airports. I know the feeling of the middle seat on a red-eye flight intimately. I’m fluent in TSA jargon, and my carry-on bag has seen things you wouldn’t believe. I’ve seen enough lukewarm airport coffee to last three lifetimes.
This is why the ultimate dream—the glorious, shimmering beacon of success—isn’t a late-night set or a Netflix special. It’s the private jet. And let me tell you, the things I’d do for that kind of air travel are humiliating, ridiculous, and absolutely worth it.
Last weekend, I got a taste of just how low I’m willing to go during a gig at a swanky corporate retreat. The organizer, a man named Chad who looked like he swam in dollar bills, casually mentioned his plane was being refueled and asked how I was flying home. When I mumbled, “Uh, budget carrier, 5:00 AM connection in Dallas,” I saw a flash of pity in his eyes.
That’s when I saw my opportunity. It was time for some high-stakes crowd work.
The Dignity Auction
My act was going well, but it needed to go great. I locked eyes with Chad and decided to use the entire remaining set to prove my worthiness as a potential, albeit temporary, jet-setter.
I started small, asking him where he was flying next. When he said Vegas, I launched into an improvised, three-minute ode to his excellent taste in vacation destinations, delivering a mock weather report for the Nevada desert that was entirely in song. It was painful. The melody was awful. But Chad smirked. Progress.
Then came the real test. I noticed Chad was wearing a truly hideous velvet jacket—a deep, bruised purple. I leaned into the mic and said, “Sir, that jacket looks expensive. It also looks like the lining of a Victorian-era coffin. Which one of your ex-wives is responsible for that fashion choice?”
The whole room gasped, including my own internal monologue. But Chad didn’t gasp; he bellowed with laughter.
I knew I had to push further. I got down off the stage and walked straight over to his table. I looked down at his perfectly polished shoes and, without breaking eye contact, dropped into a slow, full curtsy.
“Your Highness,” I announced to the room. “I, your humble court jester, request passage across the skies, for the carpeted floor of the jet is preferable to the vinyl floor of the public lavatory I currently use as a pillow on layovers.”
The room erupted. It was the most embarrassing, most subservient, and most successful piece of crowd work I’d ever done. I was literally begging for a lift on bended knee, turning my desperation into a joke.
Chad was wiping tears from his eyes. He leaned in and shouted over the applause, “If you can bring me coffee tomorrow morning at 6 AM, hot and exactly two sugars, you’re on!”
Did I haul myself out of bed at 5:30 AM after a late night to fetch Chad coffee? Yes. Did I get the recipe exactly right? Yes. Did I endure an hour-long flight being told about his yacht’s interior design choices? Absolutely.
But when I stepped onto that private plane—just me, Chad, and a co-pilot—I didn’t care about the servitude. I was sipping champagne at 30,000 feet, thinking: Dignity is overrated, but a private jet is forever.
And yes, I made sure to take plenty of pictures for future use. 🤣
