The slice of Boston real estate encircled by Roxbury, Back Bay, and Chinatown was the center of the city’s jazz universe, as well as one of the essential stops on the nationwide music circuit, in the 1940s and ’50s. It wasn’t strange to see Duke Ellington or Cab Calloway stroll up Mass Ave on the way to a Saturday night gig or heading to the legendary black musicians union, the Local 535, which was once located on Columbus and then later on Mass Ave.

Fast-forward to 2017. The South End is home to a young MC who raps under the name Avenue and who’s striving to contribute to that musical legacy. With a new album, Mass Ave & Lenox, which is built on jazz and soul samples like the hip-hop of his youth, the 25-year-old artist pays tribute to iconic memories and fixtures of his city, some of which, like the long-gone South End sneaker Mecca Harry the Greek’s, are no longer with us. On a mission, he seeks to prop a neighborhood that hasn’t always gotten its due respect.

“There’s a lot of history,” Avenue says about Boston in general. “I don’t think a lot of people know about the history from the Civil War, to Martin Luther King Jr. going to Boston University, [to] New Edition [being] from here. I wanna bring out that history. A lot of the things we do have contributed to larger cities and how they move and how they’re doing things. I wouldn’t really wanna be from nowhere else … I take pride in the city. That’s another thing that this tape is about, about taking pride in where I’m from. Taking ownership of it.”

Ave is also taking ownership of a growing national buzz, which has enabled him to build a project that is not at all about turning up, popping molly and percocets. The follow-up to his 2012 effort, Words Speak Life, and 2015’s The Chandelier View, this outing—his official full-length debut on BAU/AR Classic Records—builds on his enduring rep for honest street tales that the father of one has gained. Personal, thoughtful, and thoroughly gangster, Mass Ave & Lenox paints a picture of a place where street legends are valued as much as the traditional historic figures for whom buildings and squares are named around Boston. Ave’s home is a spot whose story he’s been preparing to tell for his entire life, and that’s been waiting for an artist of his caliber to come along and spit the tale.


Five years before Ave came into this world, in 1987 his South End got a serious facelift when the elevated Orange Line tracks came down and sunshine hit some buildings for the first time ever. With a redevelopment plan in place at the aging Lenox Street housing projects, which were built in the 1930s, low-income families were also poised for major changes. A $60 million operation took advantage of the South End’s prime location and with mixed results attempted to transform the notorious developments into a rising mixed-income neighborhood.

“It’s very diverse.” Avenue breaks down the demographics of his stomping grounds. “It’s split up pretty well—there’s Latinos, there’s Blacks, there’s a lot of white people … Depending on where you at in the South End … it’s pretty mixed up. It wasn’t always like that, gentrification got the best of it. Growing up, it was predominantly Black and Spanish … it’s a lot different now. [Crime] still [goes] down, but it’s a lot different now … there’s a lot of cameras and shit around.”

Notorious B.I.G. once lamented, “Things done changed.” As Boston’s next big voice in hip-hop walks around the hood where he ran into trouble as a youth, the same observation surfaces. Namely, it is impossible for Ave to ignore all of the million-dollar cribs that stand where burnt-out brownstones were once a common sight.

The way this area looks now is a far cry from the South End of the ’70s, ’80s, and ’90s. When Robert “Problak” Gibbs grew up in the Lenox Street projects, Boston gang members sported college or professional team logos to identify their affiliations. Things were far more brutal, with a homicide rate more than double what it is nowadays. Now the co-founder of Artists for Humanity, where he serves as a director, Gibbs recalls youths in the South End back in his day wearing St. Louis Cardinals caps, while leading local acts like TDS Mob and Rusty the Toe Jammer repped the neighborhood on Boston’s rap scene. That history considered, Gibbs was taken aback when he first heard of Ave and his project.

“Mass Ave is huge,” Gibbs says. “[It] goes from the ass-end of Dorchester to the nosebleed section of Arlington. You can ride the Number 1 [MBTA bus route] and see the total shift in people that ride the shit. So for someone to call their shit that, I was like, ‘Wait a minute. He’s really from around the way.’” While Gibbs remembers “plenty of rap cliques that came out of the bricks,” he says far less have sought to represent such an enormous stretch. It’s a lot of real estate to cover.

Even with the machinations of municipal planners, the South End—or “Southside,” as Ave and his compatriots call their neck of the hood—isn’t all dog walkers and lattes just yet. The craziness of the crack-filled ’90s and 2000s still resonates on many blocks, with certain aspects of life here as raw as they ever were. On Mass Ave and Lenox Street, the corner for which Avenue’s debut is named, the proof walks right up to us during the interview for this profile. As we’re taking photos, our microphones and cameras in full view, a disheveled man approaches to ask Ave if he’s “holding.” After being denied, the man sulks off, and Ave turns to the camera. Without saying it out loud, he smirks to suggest that he’s gloating: See, I told y’all.


Hip-hop wasn’t always in the cards for young Avenue. As a teenager at Cathedral High School in the South End, he dribbled his way to a basketball state championship and later had a chance to play in college. By that time, though, he’d started to get in the mix back in his neighborhood, and he was eventually expelled for selling weed on campus.

The whole time, Ave had front row seats to hardship. When the rapper was a toddler, his father had been locked up at the nearby South Bay House of Correction, while the perils of his hood were omnipresent. (His pops, now a free man, regularly volunteers at jails and uses his story as a cautionary tale for young people.) So with school and basketball off the table, a few years ago he turned to his other love, music, and in relatively short time developed the ability to analyze the streets with a skill far beyond his years.

His knack for storytelling comes in handy. When authorities pulled 27 people out of the Lenox Street projects and surrounding areas last March, for Ave, it was more than a story about alleged gang activity splashed on page one of the newspaper. Those were childhood friends who were removed from his life. Avenue explains:

“Regardless of everything that goes on around it, the whole gentrification phase, [the South End is] still real within a certain circumference. It just brought back a lot of emotions, a lot of shit that I remember from when I was growing up … so I wanted to tap into that.” His vivid track “27 Reasons” came out of this experience. He continues: “When the raid happened, it kind of solidified the whole mood [of the project] for me. It affected me personally … I went from having a phone full of contacts to it not ringing at all.”

From there, he dove into the beats. “I didn’t have no choice but to lock in and focus on the music. That was me being like, ‘This is go time.’ And the whole time, I was going … ‘Let’s just put it all in the music.’

“After being in the neighborhood for so long, it was just me feeling like me and the people I’ve been around, we took so many [losses] … Whether it be losing people to the system, really losing people. I feel like those two street names [Mass and Lenox] really got the best of a lot of people in certain situations. I feel like this would be the way to flip it. It’ll be our turn to take ownership of those two names and everything that stands behind it.”

A baby-faced rapper with a youthful voice, Avenue is looking for more than success. With Mass Ave & Lenox, he’s attempting to do something that is necessary for himself as an artist: He wants to help heal his hood.


How do you represent the sound of a section that is home to one of the oldest jazz clubs in America as well as some of the great Boston rap artists?

You start by getting a team that understands the stakes. An introduction from Brendan Boyd, one of the co-founders of the Boston-based clothing company Society Original Products, put Avenue on Frank “The Butcher” Rivera’s radar. An internationally known sneaker aficionado and streetwear stalwart, Frank is primarily known in hip-hop circles for his fresh collaborations with brands such as Puma, Nike, New Balance, and Reebok. Lately though, he’s been focusing on music under the umbrella of his larger creative company, Business As Usual.

Working together for the first time last year, their early collaboration resulted in the track “Ungodly,” which was the genesis of the Nineteen Ninety Now sound that Ave and Cooking To Kill, the production duo of Frank and Boston Music Award-winning producer The Arcitype, have honed. For Mass Ave & Lenox, Cooking To Kill oversaw a moody yet melodic sample-based vibe—also supplied by Latrell James and Tedd Boyd, Joe Cutz, OG Wally West, and D Sanders—that pushed the young MC to a higher lyrical level. For Frank, it was a no-brainer to have Ave become the flagship artist for Business As Usual.

“It had everything that I was looking for, it had everything that made me want to work,” Frank explains. “Everything that stimulated me … he had the story, the talent, the temperament. Our relationship was very natural; it clicked. He allowed me to weigh in and give advice. That’s the bulk of the magic. This project is that new realm of possibilities. It’s worthy of national recognition, it’s not just great on a curve. It’s for the city, but it’s designed to point out and attract. He wants to represent a story but present it in a way that’s realistic and with a tone of We can do better, let me show you we can do better. I couldn’t ask for a better situation.”

With nationally touring guests like Royce Da 5’9” and Smoke DZA, as well as rising artists like Deon Chase, Prano, and Ariez Onasis—all fellow members of Frank The Butcher’s BAUEWYK collective—Mass Ave & Lenox is an updated version of the hardcore authenticity that Jay Z’s Rocafella camp and Cam’ron’s Dipset first gave the world. Nevertheless, at a time when mumble rap rules, Ave isn’t worried about appeasing the masses to gain the public’s attention.

“I don’t really get caught up in what’s going on, what other people may be doing, what’s poppin’ on the charts,” he says. “I just try to make what I like … I make what I love. … it’s reminiscent of a lot of the music I was listening to growing up, [the] soul samples in Cooking To Kill’s production. I’m really rapping on that, I’m really telling a story. The whole thing is based on true events, that’s the whole theme of the project. A lot of it is real events, all factual.”

“This is very much a youthful album,” Frank says. “I had to step back and say, ‘Okay … how do we elevate without changing the color [of the music]?’”

Adds Arcitype: “The whole crew is [willing] to go against the grain. They had a willingness to be open to something different that would help them stand out in the long run. That’s not an easy thing to see at an early age, to understand that sometimes doing things against the grain puts you not in the lane of everybody else but … can help carve your own sound and distinguish you as an artist. [The idea is for us to] make a sound that could resonate, but that felt like something new.”

Coming from a city where the mere presence of Black people is questioned by ignorant hip-hop fans from elsewhere and where our musical history is often forgotten, Avenue is offering a better understanding of his hometown for everyone. With Mass Ave & Lenox, he’s representing Boston, and hip-hop, in the most proper way that he knows how, with a picture of the past and present on record. For Gibbs, Mass Ave & Lenox captured the hood perfectly.

“When I listened to Ave’s project, it made me think of how big he [makes] our block feel,” said Gibbs, the Artists for Humanity director who grew up around the way. He describes the sound: “Here’s the updated version of what we were experiencing back in the day. It sounds definitely like he’s an old soul … He’s speaking in a code that he’s not giving away everything. He paints [a] picture like how you would listen to a Nas song. You almost have to be from there to know what he’s talking about. It’s slick talk. He’s next.”

“I don’t know if I could put an exact or specific guideline on it,” Ave says of his writing method. “I just know how I’m gonna go about doing it. It’s just straight forward. It doesn’t get any more straightforward than Mass Ave & Lenox being the title. If you know me, you know what I represent, you know what I stand by. Basically, I feel like if Boston’s gonna be represented the right way, it has to be by somebody who really comes from that background, somebody that people can identify with.”

Around My Way (#AMWKBX) is a collaboration between KillerBoomBox, the Boston Institute for Nonprofit Journalism, and DigBoston. To support long form music and arts journalism become a BINJ Reporter Supporter (underwriting inquiries please email fara1@binjonline.org), and stay tuned for upcoming installments plus bonus audio and video components.