Can Comedians Get Rich And Stay Funny?

Some comedians struggle to stay funny or likeable when they make it. Once you’re a millionaire partying with the Saudis, it’s possible to lose some of the sharpness that made you so popular in the first place. Bill Burr and Dave Chappelle come to mind.

Money changes you, and no one is more aware of that than comedians who have just “made it” or are just about to “make it.” Enter Stavros Halkias, 36, and Caleb Hearon, 30. 

Halkias, the host of Stavvy’s World, just had his debut role in an Oscar-winning director’s film. He stars alongside Emma Stone and Jessie Plemmons in Yorgos Lanthimos’ new Bugonia. Plus, he’s going on his nationwide The Dreamboat Tour and getting fancy profiles written about him in The New York Times.

It’s a far cry from where the comedian was on the now-defunct Cum Town podcast. Hearon is experiencing a similar rise to big-time fame. The comedian hosts the podcast So True, and is racking up film and TV credits, including the upcoming highly-anticipated The Devil Wears Prada 2. 

In the most recent episode of Stavvy’s World, the pair discussed what it’s like to rise from one tax bracket to another—especially when part of your public image has been a relatable one for working class people. 

“You’ve changed,” Hearon said to Halkias after observing his new podcast studio has an actual doorman.”

“Look, dude. What can I say? I'm subletting an insane rich man's apartment for 6 months. I'm cosplaying like a wealthy captain of industry,” Halkias replied. 

“We weren't supposed to be in these spaces,” Hearon said.  

“Not at all,” Halkias agreed. “But I told you this. You're 6 years younger than me. I know where you are. I was 30 and about to get rich and being like it'll never happen to me. No, I'm a, I'm salt of the earth and you're clinging hard to it. It's very hard. It's important for you, as particularly your image, to cling hard to it. You know what I mean? And don't get me wrong, me too on some level. I’m from Baltimore. I talk about inequality as a big problem. I listen, I bought a new car. I bought a RAV 4.” 

“Now, was it a $55,000 RAV four?” Hearon chimed in. 

 “It was the absolute highest RAV 4 possible,” Halkias confirmed. “Fully loaded RAV 4. I wanted the cameras up top so that I could uh, you know, parallel park with ease. I've been a pedestrian in New York for too long…But, did I test drive every luxury SUV and was too fat for the seats? Yes.” 

The conversation continued and included a major swipe at the other podcasts helmed by comedians who are ultra rich and have decided to use that privilege to host President Donald Trump on their shows. (Looking at you, Theo Von, Andrew Schulz, and Joe Rogan.)

“I was getting ready to make that move. You know, we're about to reach out to the Trump administration's press secretary and say, I know he's not running, but could the big man squeeze us? Could the big man squeeze in Stavvy's world?” Halkias joked. 

“Can Savvi throw him some softball questions that make it look like he has no point of view?” Hearon added. 

“Could I humanize a piece of shit?” Halkias continued. 

Clearly, both comedians are aware that getting rich is a fast track to potential integrity-rot. There’s nothing more alluring than selling out; that’s always been true, yet there’s a comedian junkyard full of comedians who cashed checks blindly. But hearing this conversation from people who are a) aware of that possibility and b) are just now being faced with those actual decisions is affirming that some people at least think about the process. 

Get your money, guys. But keep trying to find that RAV 4 balance moving forward.