photo by Bred Hampton

Around My Way: Jefe Replay Is A Rox Star

Orchard Park taught him how to master his Proper Finessments. Now it’s time for heads in Boston and beyond to make way for a Rox star

by Brendan McGuirk,

photos by Bred Hampton

It’s a sunny winter Saturday in Dudley Square, and Jefe Replay’s in his element. The rapper’s doing what he often does—walking around town looking fly, carrying a brown bag with a bottle of Hennessy. Since public drinking is illegal, the cognac’s glass vessel is capped, but who’s to say what Replay’s sipping from his styrofoam cup?

What hip-hop heads around here know for sure is that the second track on Replay’s recently released debut, Proper Finessments, begins with the distinctive sound of an iced-down beverage being swirled around a disposable cup. The loophole is Jefe’s finesse; while the contents may be unconfirmed, there’s a hint on the song “Roxbury Syrup,” in which he describes his preferred beverage as Henny and iced tea.

But today? It’s anybody’s guess.

Jeff Revelo grew up less than a half mile away, in the Orchard Park section of Roxbury. Since making music and building a following for nearly the past decade, nowadays most people call him Replay. Or Jefe. Or Juan, as his branded merchandise tells fans to “Ask For Juan.” At the center of it all is Jeff pulling the strings. He may use many names, but he’s always himself.

“It’d be dreadful trying to be something else,” the proudly self-possessed 25-year-old says.

Posted up in a crosswalk by the Dudley T station, Replay brandishes his not-terribly-mysterious cup. But while trying for a photo, he finds himself in a young woman’s way. She’s a bit bothered by it all—the blaring crossing signal isn’t helping—but Replay is experienced at disarming situations. They agree that if she lays off, he’ll share some of what is in his cup. She agrees, he pours her a hearty swallow to fulfill his promise, and another fan is made.

“After being from a hated hood, you kind of want to be liked,” he says. “When you grow up from not being liked, you kind of want to be liked after a while.”

Replay says he was 11 years old when he realized that he hailed from what he calls a “back-against-the-wall hood.” An experience at a neighborhood hoops game at a community center awakened him to the depth of Roxbury’s internal rivalries. Suddenly, the name on the front of his basketball jersey could make him a target. It was unfair, but the threat was real.

“Our hood has murder beef with hoods,” he says. Older relatives were drafted into little-kid squabbles. By sixth grade, peers quit playing basketball.

“There’s no reason for us to be worried about the shit we was worried about,” he says.

Replay’s reaction: make more friends than rivals. Today, he’s so well-liked that people wear his shirts and sing his songs and will descend from all around to Cambridge this week for his album release show at Sonia, which he will be headlining. For that he teamed up with the promotion company N.E.O.N.E., the last subject of this Around My Way series by KillerBoomBox.  

JAM’N 94.5 DJ E Dubble, host of the weekly “Launchpad” showcase that takes the temperature of what is bubbling in both the city and the industry, has been in Replay’s corner since even before he took on his current role as tastemaker. “Listening to Replay is definitely a wave,” he says. “He can adapt, and he does it effortlessly.”

E Dubble says anticipation for Replay’s debut full-length project had been building. His breakout single “Sips Tea” dropped four years ago and has since racked more than a quarter of a million SoundCloud listens, becoming a phenomenon in Greater Boston and beyond. The bubbly Obeatz-produced track displays Jefe’s knack for crafting clever, branding-friendly catchphrases like, “Ask For Juan,” “Pay Me First,” and “Ain’t Shit Free”—all of which went on to grace merch that is very much in demand. As Replay boasts, he’s “fittin’ to go triple platinum off Ain’t Shit Free tees.”


Originally named for the distinctive rocks that once littered the area and were used to erect the very foundations of metro Boston during its initial development, Roxbury’s played a central role in Boston’s residential fabric since the 17th century. For roughly the past 80 years, it’s also been home to one of New England’s largest black communities, and as Replay tells it, in his time, his neighborhood has been defined in many ways by crime and rivalries.

“I can be on the block listening to music, keeping one headphone in, but not both,” Replay says. “You can keep both headphones in if you want [but you might] get caught snoozing,” he says.

Some of the challenges in Roxbury can be blamed on government mismanagement. A 1985 study of Orchard Park put responsibility for the economic downturn on abandoned plans for a Southwest Corridor, which decades prior had promised to connect places like Jamaica Plain and Roslindale directly to downtown. But stalling brought issues, with Roxbury caught in the middle. On-ramps were left incomplete and deserted, and the eventual abandonment drove out vital manufacturing jobs. The report also laid blame on political neglect, or what we might call institutional racism these days.

In the mid-1980s, while then-President Ronald Reagan pivoted the nation to a war on drugs and squarely away from systemic solutions to address economic disparity, blighted parts of Roxbury like Orchard Park became an obsession of white folks. Even as Bobby Brown, a favorite son of the original Orchard Park Projects that have since been demolished, dominated pop charts along with his groundbreaking group New Edition, and as hip-hop grew in popularity and profitability, isolation and challenges in some of the Hub’s black communities intensified.

Replay grew up with 10 cousins and his uncles at 27 Adams St., directly across from Orchard Park’s namesake playgrounds. He idolized his older, cooler cousins, some of whom were ensconced in street life. As he realized his call to music, which seemed like the only outlet that could possibly support the lifestyle that he desired, Replay began using the experiences around him to create and started to experiment with his own track production. His middle school rap persona was Beantown Boogs, and along with friends he turned out cuts that he now describes as “some young, shooting-at-you shit.”

“We was rapping about regular shit that happened that I wasn’t too proud of,” he says all these years later. Before middle school was over, he was ready to move on. Beefs that had lasted for years had taken a significant toll, and while he still had great pride in repping “OP,” Replay felt his time in that lyrical theater was finished.

“Why do you think I make ‘Sips Tea’?” he asks of his ode to remaining unbothered. “Because I don’t want to be tough or anything near tough—I understand what tough brings.”

Instead of stay tough, Replay has settled on a calmer mantra: “Stay ugly, get money, we chillin’,” as another one of his songs goes. The artist even got to demonstrate his cool mentality on a national stage in 2017, when he was tapped by Nike to model the Kyrie Irving Celtics jersey for Nike’s “Want It All” campaign.

“Stay gorgeous, stay young, don’t worry about nothing that’s going on outside,” he says.

Looking back, Replay may be calm, but he’s nevertheless outraged about how young street life starts for some and how encompassing it can become. Ask and he will show you photos of his friends flashing gang signs in their middle school yearbook. Things that should have been innocent weren’t, like the time his bike went missing. “I swore somebody stole it,” he recalls. After running through the projects looking for a fight, Replay found out that the culprit was actually the Boston Housing Authority. “I almost fought my friends,” he says.

Things began to change around 2010. The response to a rowdy Wiz Khalifa show on City Hall Plaza showed him that there was an audience to be mined from the region’s teeming college crowd and gave him a new focus. Meanwhile, his other focus, basketball, led to a fateful meeting with another budding artist, Stephen Goss, who’s better known these days as Cousin Stizz.

Prior to a preseason game at Dorchester House, Replay and his teammates from East Boston High were enjoying a smoke when they realized they had stumbled into the opposing team’s hangout spot. Blunts were passed, rhymes were spat, and connections were made. “He was rapping for us for like two blunts,” Replay recalls. Stizz was a natural, but Replay, having started out as a producer, was the more experienced song-maker.

By 2012, the pair were working side by side. The collaboration gave Replay access to parts of Dorchester that he might have been wary of visiting alone. “I met different people,” he says, “I was able to get out of my hood. … I had the respect and [was] able to go places that people weren’t really going to go by themselves.”

Rapping then as Jeff Replay, he and Stizzy, as the “Cousin” was then known, were eventually joined by another aspiring MC, Nick Gray, and the trio formed the group Pilot Nation. The outfit began gaining traction in different corners of the city—Dorchester, Roxbury, the college circuit. Each artist attracted different crowds to the enterprise, which meant new advantages and opportunities.

It wasn’t long before actual money was getting made, with label deals being discussed. Stizz eventually signed to RCA, but Replay’s loyalties led him along a different path.

“I didn’t want just a ‘me’ deal,” he says. After having success building a group with people who started as acquaintances, he had aims to bring other close and gifted friends into the record business. “[I was] trying to make the best for all of us,” he explains. “I pushed away my own opportunity trying to get a group opportunity.”

Even without a deal, Replay kept on moving, assembling his own team of engineers, producers, and videographers. All on his terms. Still, he needed capital, but an attempt to borrow $1,500 from his dad to shoot a video only netted more inspiration. “He’s like, ‘You might wanna sell some merch,’” says Replay of his dad’s reaction. He took the advice, though, and invested the cash he had on hand into merchandise—pricey tees, mugs, other ephemera. The plot ultimately paid off, resulting in his father, Jeff Sr., giving his son a new, bossed-up rap nomenclature.

“When he seen me do that, he was proud of me,” Replay says. “He was like, ‘You make your own lane. You Jefe.’”


Dutch ReBelle was already an accomplished veteran of Boston’s rap scene when she first met Replay in a chance encounter. By the time that she recruited him to feature on her 2015 Kiss, Kiss EP, the two had truly connected creatively, and their collaboration, “Air It Out,” became a clear standout. Replay’s hook, freestyled as ReBelle recalls, shouts out not only his hood and yours and the hustlers, but perhaps most crucially, gives props to stoners at the cookout with two plates. “Replay is all swag,” ReBelle recalls. “Just super swag, he just has a real fly vibe to him. Real old-school fly.”

Like others who know Replay well, ReBelle also says “he doesn’t really take himself too seriously … when it comes to just creating and capturing a vibe. … Dude came out the gate talking like, $100 for a shirt. How you gonna tell Replay, who has three outfit changes in a day, that you ain’t gonna buy this fucking shirt?”

“I feel like wherever I touch down people can meet me and we can create those type of connections, and it’s just different,” Replay says. “People reach out to me to have fun. I have fun. And when it’s time to rap, I rap.”

Having grown up in the area, ReBelle knows how exclusive and closed off the Greater Boston music scene can be and was happy to make an authentic friend in the industry. “He’s been through a lot of the music bullshit that only artists who are doing this on a regular basis go through,” she says. Some of that bullshit happened as the two were heading to the 2015 Boston Music Awards. ReBelle was on the bill and planned on bringing Replay on stage, but on their way to the show they were stopped by police, and he was arrested due to an outstanding warrant.

“We were all dressed to the nines going to this award show,” ReBelle recalls, “and the police took him right out of my car.”

After a short time of working the BMA crowd while being concerned about her friend, Replay walked in the door. “I ran over to him and it was a whole hoodrat beautiful moment, because I’m like, ‘You’re not in jail?’ He, being Replay, convinced the statie to drive him back to the show.”


Crediting it to his days observing the hustle, Replay has always been a systemic strategist. He pays attention to how acts of all sizes move and is far more interested in their tactics than in trends. With his lessons on hood likeability under his belt, Replay came to an important realization about the music industry.

“This is a people business,” he says. “We could be out back smoking and you just need a light and then we just converse and you don’t even know I make music, and that’s kind of where I make my bread and butter.”

As music empowered Replay to tour and meet more people, he realized that in order to achieve the success he hoped for, he needed a coalition. “I needed everyone in Boston, not just Roxbury,” he says. “I’m going to fuck with whoever’s nice.” ReBelle says, “He’s really in tune with the vibes of people around him.”

Whether as Jeff, Jefe, Juan, or Replay, the man’s career is a trail of encounters that begat friendships. One connection that he needed came when Replay’s world was getting hot, with people getting killed around him. One friend he had made along the way came through and put Jeff up in Cape Cod for a summer, hooking him up with a place to live, a job working construction, and a chance to avoid troubles.

“I needed to get out of the city because I knew the summer was going to be crazy,” he says. “Let me just remove myself. … I’m out there getting legal money … chillin’, summer vibes. I was showering outside because it was beautiful.”

Replay says it didn’t seem like a big deal being a token black guy in Harwich, Dennis, and Orleans, though the experience did give him a new perspective on the hip-hop marketplace.

“This is why we hang around white people,” Replay says. “We be like, Damn dog, trade with us. And everybody that’s like curious of the culture—trade with us. We would trade in an instant. … We love the knowledge that the hood brought us, and the hood is lit,” he continues, “but people coming from places like Orchard Park would rather [not] have to worry. That’s what that summer on Cape Cod was about.”

When it comes to developing a cohesive and vibrant hip-hop audience in Boston and New England, E Dubble of JAM’N says the biggest hurdle is the all-too-common instinct of artists and fans to stay in their own familiar circles. As a DJ for a station that serves hip-hop fans across the region, he finds the distinctions that some draw over territory—who’s from Boston, who’s not, who’s from which block, and so forth—to be largely counterproductive. “How is it that we are smaller [than places like Atlanta or New York],” E Dubble asks, “yet more segregated?”

In a state where people can be stingy with attention, E Dubble finds it truly exceptional that Replay has captured such a serious audience. And he says his sound and style are now forging something of a moment around town, complete with imitators.

“[It]’s almost like kind of how Travis Scott has his influence on what’s going on right now with the darker beats and all that type of stuff,” E-Dubble says. “I would say that’s what Replay has done for the scene that we have up here. … I feel like a lot of these kids either live the lifestyle similar to Replay or want to live the lifestyle. He has influence on people who actually are buying into him. … It goes hand in hand with the lifestyle. Everything that he’s selling is true to who he is.”

“A lot of people [are] living vicariously through me,” Replay adds. Some of his fans, he says, “see no way” to escape their circumstances. He knows the feeling.

“I just like being an open book to where people can pull up on me and just know that you’ve been through the same shit that I’ve been through,” he says. “I ain’t nothing different from anybody else.”


At one point not too long ago, parts of the fast-money life caught up with Jefe. Legal troubles held back his creative output for years, leaving rapt fans wanting.

“I don’t make excuses,” he says. “I paid for it. I paid financially. I paid with my time. I paid with my focus. That’s why my album wasn’t out.” Nevertheless, some hardships bore creative fruit, like when an outstanding warrant left him unable to fly to the career-making South by Southwest music festival in Austin, Texas. Replay drove instead, and wrote about it later on. “That’s what the first song on the album is about.”

Replay says that track, “A Different Road,” fully encapsulates what it took to put legal issues and old habits aside, and to focus on being the artist that he knew he was prepared to be. As a whole, Proper Finessments became a chronicle of the saga he was living.

“That shit was a fucking journey,” he says. “That was a journey for my creative freedom, for everything.”

ReBelle, who had become a close enough friend that she attended his court dates, puts it in perspective: “Replay was really fighting for his life at one point. Fighting for his freedom. … I listen to the project and it just makes me emotional and shit, because for me it’s like I know what he’s talking about.” E Dubble adds, “He was in a mental space where music wasn’t his priority because of other things he had going on in his life.”

The past few years of Replay’s growth is reflected throughout his debut, which finds him sharing recent parts of the story at the front of the tracklist and packing his familiar fan faves at the end. “Some of these songs are older, some are brand new, and the flow of it is what people like,” Replay says, adding that people who know him best have said that “it sounds like the progression of how you came to make this project.”

After the dust settled, it was time to refocus on art. But Replay still had his concerns, notably that he had to live up to expectations built over the years. “I was very anxious,” he says about dropping Proper Finessments, which finally came out in February, the release date reflecting his Roxbury zip code, 02119. “I’m grateful that it definitely worked.”

Now that he is in the clear legally, Replay is able to focus creatively and continue the heavier output of years past. He’s also been able to separate himself from the street.

“Every time young motherfuckers run up on me thinking I’m a certain way,” he says, “I let ’em know I’ve been let that go. I’m focused on this, because that shit is only a destructive mindset.”

E Dubble says that despite Replay’s surge in popularity, the artist has remained accessible and relatively carefree: “I’ll be on Newbury Street just sitting by the park or in traffic, and he will just roll past me on the skateboard. It never fails. He be having a bottle of Henny on him and everything. Dude is wild.”

“Boston has to see something different,” Replay says. “If you don’t know who you are before you step outside, you are bound to be influenced by the littlest shit.”

“We all have our favorites. I just want to be one of them.”

Around My Way is a collaboration between KillerBoomBox, the Boston Institute for Nonprofit Journalism, and DigBoston. Stay tuned for upcoming installments plus bonus audio and video components. To see more long-form music and arts journalism, you can support us at