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Rob Santos is Coming Out

From NYC to Connecticut, from open mic nights to health scares, lost deals, and legal battles, stand-up comedian Rob Santos is ready to share his story.

Written & Photographed by
Jasmine Jones

“My mom calls me gay all the time,” Rob casually states. He, his girlfriend Erica, and I are settling in for our interview while looking over Chinese take-out options. “She calls me gay so much that [Erica] thought I was gay.” Even though they’ve been together for 20 years now, Erica explains that his mother, to this day, will often randomly say things like, “You know he’s gay, right?”

He might not be gay (sorry, Rob’s mom), but he is ready to come out. Rob Santos has been through a turbulent series of events in just the last ten years. From making headway as a comedian in NYC and being recognized by others like Sherrod Small and Artie Lange to moving back to Connecticut to focus on his mental health and the birth of his daughter, Brooklyn. From finding comfort in attending open mic nights and comedy shows with his crew of budding comedians, including Ricky Velez and Pete Davidson, to health scares, lost deals, and legal battles, Rob Santos is ready to share his story.

Early life

Rob doesn’t think he’s the funniest person in his family, but he has always known he could make people laugh. On a hot summer day, sometime in the late 80s, 4-year-old Rob walks into his house and says, “It is hot as hell outside.” Everyone laughs, and he gets popped in the mouth by his mother. At that moment, a young Rob thought to himself, “Ooh, I want this.” He had just made a room full of adults laugh. The quick pop couldn’t compare to the feeling of the laughter that filled the space—laughter that he knew he had caused. By 6, he was sure of two things: his ability to make others laugh and his desire to make money doing so.

He began watching comedians like Eddie Murphy, George Carlin, Lily Tomlin, Dave Chappelle, Richard Pryor, and Lenny Bruce, to name a few. He allowed any and everything to inspire him. Whenever he laughed at something, his mother would ask him why he thought the joke was funny, which got him thinking about why others laughed at certain things. While watching comedy shows with his friends, he would pay attention to what they found funny, how much they laughed, and how often they laughed, studying these things to understand the essence of comedy. By 12, he had Eddie Murphy’s Delirious memorized by heart, courtesy of his Talkboy recorder, which he’d leave in his living room to record the set as it played. He would later listen to the tape, learning and absorbing all that he could from one of the greats doing what he dreamed of doing.

Rob’s first head shot in New York City, 2009

“At the time, when you’re a comedian coming up in New York, you want to find a club, a home club, do as much as you can, find your place, and then go on the road. But no one gets exactly what they want.”

New York and Connecticut

In 2011, after spending 3 years in New York City trying to “make it” as a comedian, Rob Santos decided to leave and focus on his mental health. As hard as it was to go, it was a choice he felt he had to make. The upcoming birth of his daughter and his continuing struggles with borderline personality disorder (BPD) were the main reasons behind the decision, but it’s not one Rob regrets. Now, at 39, he questions if he should have been there and if that was his place. “At the time,” he explains, “when you’re a comedian coming up in New York, you want to find a club, a home club, do as much as you can, find your place, and then go on the road. But no one gets exactly what they want.”

He describes his time in New York as being overloaded with choices and constantly questioning whether or not he was making the right ones. Subtle things would get to his head, such as seeing his friend Ricky Velez’s segment on Comedy Time featured on the show’s main YouTube channel while his segment was cast aside to their subchannel, Comedy Time Latino. Or the moments he would watch his friends go from hanging with him at a comedy show one night to performing on professional shows the next night. “I was upset, but as the opportunities were presenting themselves, there were a lot of guys doing things… that I didn’t do, I didn’t want to do,” he alluded. “There were guys making choices to get ahead, and I was like, ‘nah, I’m good.’” Although he knew he would never make those choices, he recalls making other poor choices, mainly chasing after women.

As Rob watched those around him get ahead, he felt like the world questioned his value. He couldn’t be anyone other than himself: a Black and Puerto Rican comedian with identity issues and borderline personality disorder. However, it was clear that the corporate world wanted someone who looked more like Chris DiStefano or Pete Davidson, but with Rob’s talent and comedic style. Interestingly enough, as Rob was getting ready to move back to Connecticut, he spent more time with Pete, who was very intrigued by Rob’s jokes about being racially ambiguous.

At the time, Pete was an unknown teenager trying to make it as a comedian in New York. He and Rob would talk jokes all the time. “I love the dude, but he was never really that good. But he was also only like 17 or 18, and he was hungry,” Rob says, “And he’s a nice guy; he’s very charismatic.” Pete would often invite Rob and other mutual friends of theirs to his shows at Times Square Art Center. One night, Pete shows up wearing an “N” chain. He had just met with Nick Cannon, who wanted to work with him. “I said to him, ‘Dude, your life is gonna be different.’ But I made a choice to leave. I know that if I had hung around, I probably would be riding with him right now. But I wasn’t willing to make the choices he and others were making. On top of that, I was scared out of my mind about this baby and not feeling myself upstairs. So, one night he’s showing us the “N” chain, then I move. It was tough.”

Rob performing at Mohegan Sun in Connecticut, 2013

Back in Connecticut, Rob would see his New York friends getting more and more opportunities, such as starring on various comedy shows. “I had to watch Girl Code and Guy Code and this code and that code, you know? VH1’s I Love this decade or that decade. I had to see all these different things unfold before my eyes.” He was happy for them, but it was bittersweet. Eventually, Erica came across some of Pete’s standup on YouTube from 2012, right after Rob left. According to her, the jokes sounded eerily similar to Rob’s work about being racially ambiguous. The same work that Pete complimented Rob on right before he left New York.

“He was making a comment about people not always knowing that he’s white because of his looks, talking about being racially ambiguous as a white person,” Erica remembers. When she showed Rob the clip, it shook him. “I was upset, and then I suppressed it for a long time,” he tells us. “I haven’t spoken to him in like, ten years. When he got SNL, I called him, and I got, ‘The number you have reached….’ But I wanted to congratulate him because that’s my man, you know, we were legit friends.” Rob states that he was never mad, just shocked, hurt, and discontent, all masked with anger because he couldn’t identify any other feelings.

“Identity and confusion about identity were big in Rob’s act and in his life,” Erica explains. “It was something so personal to him, and then you see someone else doing something very similar, but who doesn’t actually go through identity stuff. It’s just a joke about how he’s white and doesn’t always look white. But to Rob, identity at that time was so personal and such a big thing for him that he often had it in his act.” And it still is a big thing for him. Rob doesn’t like to call it appropriation because that’s a heavy word, but he feels his DNA is in Pete’s work. He’s dealt with comedians blatantly stealing his jokes and has inspired other established names, but Pete never actually stole his jokes. He instead took the essence of who Rob was and waited until he left New York to do so. “Pete also has borderline personality disorder,” Rob adds, “So now he’s the identity guy and the borderline guy.”

Fast forward to 2015, Rob finds himself going back and forth between New York and Connecticut for the next two years. Watching someone else take the essence of his work was a challenge, and he had a massive chip on his shoulder and worsening BPD symptoms as a result. He began going to group therapy; in March of 2017, he discovered Dialectical Behavior Therapy (DBT), and in August, he had his first breakthrough. It was that same year that Erica was diagnosed with cancer. And in true Rob fashion, he dealt with that news by creating a bit in his stand-up about it, which expressed, in his way, the emotions he felt while watching her go through this battle.

“I was jealous because everyone knew how to respond to her. Here I am, two years removed from running to New York, and I couldn’t tell anybody that I’m not right upstairs,” he explains. “She’s got this big thing coming up, and I’m making it about me because I don’t know how to tell her that I’m scared. I couldn’t articulate those feelings properly. She understands it now, but at the moment, it was tough. So when I do that bit, it’s a reflection on everything.”

Rob performing at Gotham Comedy Club in New York City, 2017

“I had a contract and everything, ready to go. Eight episodes, 26 minutes, 36 seconds, Beige on Both Sides on the Spirit network at 10 o’clock.”

Beige on Both Sides

In 2016, Rob began working on an idea that had been in his head for a while—the story of a comedian who has just come out of a mental institution. In his desperation to get this story out of his head and on paper, he decided to work with friends who seemed eager to help, which taught him that everything comes at a price. While Rob was more interested in getting the show written and shot simply with his friends, one “friend” had other plans. They began investing too much into the project (despite being told not to) and pulling in all of their connections when they saw its potential. Rob started to express no longer wanting to work with them, and they would remind him of how much they had already put into the project, holding those contributions over his head.

By 2018, they were ready to showcase the series, titled Beige on Both Sides, premiering the first two episodes at the Mark Twain House and Museum. However, by this point, Rob is miserable. What premiered that night was unrecognizable compared to his original idea. “It was white washed for white people,” he recalls, “as if white people can’t withstand to see a real version of what Black people experience.” And it broke his heart, which only continued to break throughout the evening. It broke as he watched the audience loving this new, desensitized version of his idea, as names he didn’t recognize rolled through the credits, and again as his friend took center stage at the end of the show to give a speech on their hopes and dreams. A speech that conveniently forgot to mention that Rob was the one who approached them with the idea in the first place. What was originally created as an apology letter to Erica for all that Rob had put her through quickly turned into a safe, white-friendly vessel for this person to jump-start the career and fame they believed they deserved.

When Rob got a meeting with Connecticut Public Television (CPTV) after a chance encounter while working at an Apple store, things started to pick up quickly. CPTV saw a 90-second clip of the show, and they were immediately interested. With new additions to his writing team and a deal with YUPntwk and CPTV, Rob was set. “CPTV wanted to invest a lot of money into the show when it was Beige on Both Sides,” he recalls. “I had a contract and everything, ready to go. Eight episodes, 26 minutes, 36 seconds, Beige on Both Sides on the Spirit network at 10 o’clock.”

This high, however, did not last long. The deal became null when the same person who held their contributions over Rob’s head refused to sign off that they were no longer a part of the project. CPTV was not interested in working with them, they wanted Rob, which was a reality that this person could not handle. Rob lost the deal, and after going to social media to call this person out on it, they sued him for defamation. When he looked for support from the creative community around him, the only help offered was to “kill them with success” because, as he states, “That’s what we’re trained to do, we’re trained to turn the other cheek.”

Once again, Rob was faced with the pressure of making a choice, while his peers blamed him for making all the wrong ones. “It was tough because I was so desperate. I got tired of driving to this place and that place for $50 or $100. I’m tired of opening up for the guy coming in that people want to see,” he admitted. “I don’t want that anymore.” But Rob knew that if he went against his morals then, it would be no different than if he went against his morals in New York; It would be scorning what his family did to help him, and all of the sacrifices he made to get to this point. After letting this person know exactly how he felt, they took his name off as the creator of his show and went on to promote it as their own. Even with a premise based on Rob’s life, and with Rob as the star of the show, Beige on Both Sides was taken and promoted as someone else's work. Although the intellectual property belonged to Rob, since this person paid for everything, technically, they owned the content, and went on to make a good amount of money off of the show.

Rob with his daughter, Brooklyn