Comedian Aruba Ray Ellin on escaping NYC burnout to build Aruba's top comedy club

For New York comedian Ray Ellin, stand-up comedy has been many things: an escape from crushing city burnout, a successful business in the Caribbean, and a literal lifeline. Following the devastating loss of his sister early in the coronavirus pandemic, Ellin found solace not in quiet reflection, but in the relentless hustle of virtual performance and online corporate trivia.

Yet, the driving force behind the top-rated Aruba Ray's Comedy Club openly admits that navigating the fine line between entrepreneurship and creative pursuit is a constant battle, he told the Dam Yankee podcast. The struggle forces him to question whether building a brand ultimately gets in the way of becoming a more widely recognized comic, he said on the show, out now on YouTube, Spotify, Apple Podcasts, and more services.

After all, Ellin is so at home performing on stage, that a Dateline NBC piece found his blood pressure actually decreases when he begins a stand-up set.

Finding a Lifeline in the Digital Space

When the pandemic brought the live entertainment world to a grinding halt, comedians everywhere were forced into isolation. For Ellin, the lockdown coincided with an immense personal tragedy, the sudden passing of his sister. Rather than letting the weight of the loss pull him under, Ellin turned to the only sanctuary he has ever known: performing.

Ellin rapidly pivoted to producing live, interactive digital comedy and corporate trivia nights. This exhausting, near-constant digital hustle served a dual purpose. While it kept businesses entertained online, it more importantly acted as a psychological shield for Ellin. Throwing his energy into the technical and creative demands of virtual hosting kept his mind occupied.

"I ended up doing like 100 shows on zoom during the pandemic," Ellin explained during the episode.

The Dilemma: Business vs. Pure Comedy

This innate drive to build and produce highlights a deeper complexity in Ellin’s career. As a regular at New York City’s legendary Comedy Cellar and an executive producer for Comedy Central’s This Week at the Comedy Cellar, his creative credentials are unquestioned. However, his parallel success as an entrepreneur introduces a profound creative dilemma: does split focus hinder artistic greatness?

"I like a challenge. I like coming up with something and seeing it come to life and come to fruition, for sure," Ellin told Newmark. "Like, there's this one man show that I've been thinking about for the past year," he continued. "I would really like to focus energy on that."

Ellin openly wrestles with whether his business ventures stand in the way of him further honing his craft, and advancing to a new level where his name is more recognizable. Managing his club in Aruba, coordinating talent, and producing television requires an immense amount of mental bandwidth.

"There's definitely a lot of things performance-wise that I would like to do. Yeah, the other stuff does get in the way," Ellin discusses in detail.

The Stand Against 'Snackable' Comedy

It is difficult to say whether Ellin's lack of stand-up clips online is a defiant act of purity against all of the comedians who post their slashed together bits and out-of-context content on social media platform. After all, he frequently gets feedback from popular comedians like Mike Vecchione, who push Ellin to post more frequently.

"It's the time and the effort, and not wanting to sit and watch myself, because I just don't love doing that. And then the last thing is, how are they going to react? Less so other comedians, but just people in general, because, you know, you don't want to post something and just 20 people 'like' it," he said.

For Ellin, comedy is meant to be experienced live, where stories have room to breathe, he has time to play with the tension in a room, and an authentic relationship is forged with the audience in real time.

This full episode of Dam Yankee can be seen on YouTube, or listen to the Dam Yankee on all major podcast platforms.

Ray Ellin can be found via his website, his Instagram channel, and the Aruba Ray's Comedy Club Instagram account. He is posting content on his own TikTok account, and might restart his YouTube channel someday soon.