Mathew Silver

Recently, I met comedian Derek Gaines at Bushwick Public House, a local haunt that serves booze, coffee, and sandwiches. On a TV above the bar, the “White Christmas” episode of Black Mirror played without subtitles, while an indie-chill playlist provided background noise. Gaines is perhaps best known for playing Jaybird on The Last O.G., but he’s been building a stand-up comedy career for more than 15 years.

When Gaines moved to Bushwick, about four years ago, it seemed to mark an inflection point in his life and career. He’d just landed a co-host gig on MTV’s “Broke A$$ Game Show.” He finally had enough money for rent. Before that, Gaines was couch surfing or staying at his mom’s house in New Jersey. These days, he could move from Bushwick, but he enjoys living in the neighborhood. 

“I like how Bushwick is a mix of hood and gentrified all at the same time. It’s Fantasyland,” said Gaines, sipping an oat milk latte, his usual order. “On one side of the street, you’ll have a bunch of Puerto Ricans bumping their JBL speakers and saying cuss words and playing dominoes. On the other side, you’ll have a chick that’s into selling princesses from Disney movies at her little boutique.”

When we sat down to talk, Gaines had just returned from Phoenix, AZ, where he opened for comedy megastar Pete Davidson on the “Prehab Tour.” He seemed shy, hesitant to make eye contact. Then, when I flicked on my recorder, Gaines became the energetic, fast-talking comic I’d seen in YouTube clips. 

“Make sure this is really recording,” said Gaines. “I’m dropping gems.”

Gaines comes alive in front of the camera, which I learned while taking his photo for the piece. But the same idea could be applied to interviews. Gaines seemed ready to tell his story. It was a long journey from the early stand-up days to landing a couple TV roles. He worked as a janitor, forfeited a music scholarship, and even stayed on Pete Davidson’s couch.

Most recently, Gaines appeared on the first two seasons of “The Last O.G.” in which he plays an ex-con named Jaybird, who lives in the same halfway house as the show’s protagonist, Tray Barker (Tracy Morgan). 

Otherwise, Gaines is recognizable for his appearances on the “Will and Grace” reboot. His character, Theodore, is Jack McFarland’s (Sean Hayes) boss at the rec center. The role has surprised some of Gaines’ friends in the Black community, particularly Jeremy, a drummer at the Comedy Cellar. 

“What you doing is damn-near impossible. You might as well be in the Marvel Cinematic Universe,” Jeremy told Gaines. “You a straight Black dude, that’s the boss of a white man who’s gay, on a show on NBC. You might as well be Aquaman.”

Gaines was born, in 1984, on an Air Force base in Central California. His father, George, was an aviation engineer. His mother, Chrystal, was a nurse and tech engineer. When Gaines was 2, his parents divorced, and his father stayed in California, while Gaines moved with his mother to Philadelphia. That’s where Gaines lived from the age of 2 to 14. Because of the divorce, Gaines’ parents competed for his affection, which meant they often spoiled him. 

“I was getting love and gifts from both sides,” said Gaines. “Christmases used to be double-whammies.”

When Gaines was 14, he moved with his mother to a pleasant neighborhood in New Jersey. This background directly informs Gaines’ comedy. He describes himself as “cul-de-sac Black,” because he spent his formative years in the suburbs. Unlike other comics with a traditional rags-to-riches narrative, Gaines does stand-up from the perspective of a “Black dude from the ‘burbs that’s a tourist in the hood.” 

“Take the suburbanite and put him in the city to observe, then he goes back to the suburbs, and starts whipping up all these cool ideas of what he’s seen versus where he lives,” said Gaines. 

Though Gaines had a financially comfortable upbringing, he still had to work. At 16, Gaines took a job at Bethany Baptist Church as a janitor. Around that time, he started developing his comedy chops. He was teased at Overbrook High School for having “shitty” clothes, so he started to note the latest street fashions. He was trying to be “the fly guy.” In the event that any of his classmates made a crack about his outfits, his defense-mechanism became jokes. Gaines got good at “snapping,” or saying something quick and biting in return, from watching HBO’s “Def Comedy Jam” during the summer.  

“Big energy scares people. So, I used big energy to push bullies the fuck away from me,” he said. “While I’m doing that, I would ensure that I wouldn’t get teased by wearing better clothes. The whole thing worked out. Getting fly and getting funny all at the same time… As I’m thinking about this shit, I was an accidental genius.”

At Overbrook, Gaines was a bad student. He took the SATs twice. 

“I got a lower score the second time around,” he said. “I found out I couldn’t take tests under pressure.”

Gaines was gifted musically, though. He played the conga drums and timbales in the percussion section of his high school band. During one Christmas concert, according to Gaines, his solos had the crowd going nuts, because he knew how to make it “jazzy and funky.” His musical talent earned him a partial scholarship to the University of the Arts in Philadelphia. But he dropped out after a year.

“I was a musical dude, I just couldn’t read music for shit. That’s where I fucked up. So, it was a very Drumline Nick Cannon-type situation, where I went to the school, I was the hot-shot, but couldn’t read [music] for shit.” 

Around that time, in 2003, other kids were telling Gaines that he should try comedy. Nearby, there was a comedy club called the Laff House, where an older Philadelphia comedian, Kevin Hart, had found some success. Gaines would go to the club just to watch. Then, the day after he turned 19, he finally got the courage to take the stage. He remembers the set was bad, but apparently, one girl in the audience half-giggled. That was all the motivation Gaines needed. 

“I was like, ‘Well, that’s all I need. I’m gonna keep trying to double up and triple up on those giggles every time I’m back.’”

To support his dream, Gaines kept working at Bethany Baptist Church. He wrote jokes while cleaning the pews and bathrooms. At 24, his pastor got him a union cleaning job at the New Jersey Turnpike, where he cleaned toll booths and police stations. Then, he transferred to the Garden State Parkway, where he slept in the slop closet most days, because he was so tired from doing stand-up, in Manhattan, into the early hours of the morning. 

“Even though it was an eight-hour job, I’d clean for a total of two hours and fifteen minutes, and I would sleep for the rest of the day,” said Gaines. “The State of New Jersey paid me so much money to rejuvenate from hanging out in New York every night… Not even partying. I was hustling trying to get on the stage.”

Eventually, Gaines was fired. His employer cited “absenteeism,” a term that he still finds confusing. There was a silver lining, though, since getting canned forced Gaines to commit full-time to stand-up. The early-going was tough. He did open mics in Brooklyn, Harlem, and the Bronx. 

To attract an audience, Gaines would yell on the sidewalk outside of comedy clubs (“Hey, free comedy show tonight. Come on down!”), which is known as “barking,” in the comedy world. Those shows typically paid $10. Otherwise, he would split the contents of the donation bucket with other up-and-coming performers. 

“It’s nuts. But you do it,” said Gaines, remembering his on-street attempts to convince people to watch his shows. “‘Hey, c’mon please. Come down to a shitty, sour fucking basement. Watch people try to chase their dreams with the thoughts they had in their fucking diary.’” 

A few years later, Gaines’ agent suggested he move into Pete Davidson’s apartment in Washington Heights. This was around 2013. Gaines, then 29, was making regular appearances at The Stand comedy club in Manhattan. Davidson, then 19, was doing well, but he’d yet to join the cast of “Saturday Night Live,” which, of course, sent his career into the comedy stratosphere. 

The idea behind living together was that Gaines, being older, could act as a big brother to Davidson. As it turned out, Davidson, the native New Yorker, had a greater influence on the former church janitor. In fact, it was Davidson that introduced Gaines to marijuana, perhaps unsurprisingly, since Davidson is an outspoken advocate for medical weed. 

“He just kept passing me the joint, and I kept saying, ‘Naw, naw, naw,’” said Gaines, who eventually gave in. “It brought us closer together, ‘cause I was high now, so I kind of understood him more. So, we built a friendship.”

Then, both comics got a big break. They were both invited to Montreal’s Just for Laughs festival, which Gaines described as “the Super Bowl” of comedy, as part of the 2013 “New Faces” showcase

Gaines got signed by Gersh, a Hollywood agency that currently represents Dave Chappelle, Janeane Garofalo, and Jamie Foxx, among other big-name acts. Soon after, Gaines and Davidson started heading to Los Angeles for TV pilot season, where they each landed parts. Gaines moved out. Their careers went in different directions. But years later, Davidson reached out to his old friend and former roommate.

“Fast-forward six or seven years, he blows the fuck up, and he calls me up like, ‘Yo, man. You still my homie. You wanna come do these tours?’ And I’m like, ‘Oh shit, yeah,’” said Gaines. “The whole me coming up to the city to work on myself, moving in with Pete Davidson, thinking that was the way, I didn’t know that was something for a larger picture way down the line. And that’s kind of funny how the game work.”

And for Gaines, “the game” just keeps getting better. In 2020, he’s got a “meaty part” in “Staten Island,” a comedy written by Davidson and directed by Judd Apatow. His co-stars include Marisa Tomei, Steve Buscemi, and rapper Machine Gun Kelly. If Apatow’s past success is any indication, combined with Davidson’s recent ascension to A-list status, the movie will be a blockbuster. It could be Gaines’ breakout role.  

“I remember saying to myself, when I first started in Philly, that I was gonna wind up taking the long road,” said Gaines. “And it’s been a long but eventful road. I will say that. This shit didn’t come quick.”

Cover photo image by Mathew Silver for Bushwick Daily.

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