Twenty years ago, the Boston hip-hop scene hit a relative peak when the region’s leading promotional company, MetroConcepts, held its inaugural Superbowl MC Battle at the Western Front in Cambridge. The pivotal moment, which went down during the 1999 Super Bowl, which the Pats didn’t play in, left an eternal stamp on local music.

“This was 1999, pre-Patriots being good,” said Papa D, a co-founder of the Mass-based Brick Records. “No one really cared about going out on the night of the Super Bowl.”

Despite already having won respect through earlier pioneer acts like the Jonzun Crew, the Almighty RSO, Edo Rock (later known as Edo G), and TDS Mob, the Boston rap scene at the time had some impediments. Namely, besides college radio shows and occasional one-off events where local artists got exposure, there were few rap-friendly places to perform, largely due to policies and trends that, with very few exceptions, kept hip-hop out of downtown clubs and venues through the ’90s.

“Race is what caused most venues to avoid booking hip-hop, period,” former Boston hip-hop promoter O’Neal Rowe said.

In spite of the obstacles, Rowe and his friend Tim Linberg partnered to form MetroConcepts in 1996. Both men helped spark a Boston hip-hop revolution as they worked tirelessly to break local talents such as Akrobatik, Mr. Lif, 7L & Esoteric, REKS, Sage Francis, Virtuoso, and DJ Fakts One.

The first Superbowl Battle was a major catalyst for so much movement on the scene, as the event was stockpiled with several artists who would go on to become underground rap legends. This is an oral history of how it came to fruition and left an indelible legacy.

Tim Linberg (co-founder of MetroConcepts): Boston certainly then and even now is a very segregated community, and at the time hip-hop was premainstream. The white club owners on Lansdowne Street did not want people from Roxbury, Dorchester, and Mattapan coming to their clubs. It took a bunch of years for hip-hop to break through, and I have no doubt that race played a role on both sides for their reluctance to book and on my ability to break in.

Edo G (MC, Boston rap legend): We needed more places. The Channel, near South Station by the seaport, was in the ’80s and the early ’90s. Other than that, it really wasn’t nowhere. … We had nowhere to go. I can’t remember any place where there were having consistent hip-hop shows from ’90 to ’95. I didn’t perform “I Gotta Have It” when it came out, when it was at its height in Boston, because there was nowhere to perform it. We performed it in Cambridge at a school. That was the only place we did it.

Esoteric (MC, half of 7L & Esoteric): Venus Di Milo, Avenue C, Bill’s Bar, the Middle East, the Playhouse, Western Front, even Bahama Beach Club—I went anywhere clubs were letting people rap. I did a few odd talent contests at Chez Vous Roller Rink and lots of other venues off the beaten path when I was coming up, when grabbing the mic was a lot more scary and more of a risk than it is today. Today every fifth person has tried their hand at rapping. Back then it was, “Whoa, you rap?”

Linberg: I started DJing house parties in college, nothing of particular merit. I wasn’t a great DJ but I was into it. I moved back to Boston after I graduated college, bought a pair of turntables and started buying records. My buddy [O’Neal] and I started to get some sense of where hip-hop was being played, so we made a mixtape and went to a few clubs and said, “Hey, we want to do a hip-hop show.” And the Western Front said, “Okay, we’ll give you two shows a month.” Then we were like, “Damn, really? Now what do we do?”

We set up shop at the Western Front for a couple years on Sundays and that’s where we started doing an open mic for local MCs. It started out as a DJ thing, which was really like a bunch of friends doing parties. It wasn’t a business. Also, there was a low-wattage pirate radio station set up in Allston/Boston area called Radio Free Allston. Good people who were trying to do something pretty cool. We had a show on that station called Hip-Hop 617.

O’Neal Rowe (co-founder of MetroConcepts): When we started getting people together in ’96-’97 or so, it was clear there were so many hip-hop artists that were looking for opportunities to perform together and on a stage. Boston had a ton of talent all over the city, all different backgrounds, but venues really weren’t into opening up to hip-hop acts or DJs.

REKS (MC): The issue in Massachusetts has always been a lack of major radio push for artists. I feel a lot more of us could have broke out of the city with support from major stations. The college stations were truly a godsend.

Mr. Lif (MC): In that era, when the independent hip-hop scene was born, it still revolved around the studio. It was Butta Beats that was run by Ray Fernandes … a studio where people kind of congregated.

Fakts One (DJ, radio host): I started at WERS [99.9 FM] as a producer, which is basically like a show assistant, in the fall of 1995. I got my own show the next year in ’96.

Linberg: Fakts was like our Funkmaster Flex for Boston. … If an artist came to town, we were taking them to 88.9@Night. That’s basically as big as it got from an exposure standpoint. It was our lifeblood. If college radio and WERS didn’t promote our show, we were screwed.

Esoteric: 88.9 [Emerson College], 90.3 [Boston College], 88.1 [MIT], 95.3 [Harvard] were all very important to spreading the word about local artists with material. Most things aired on 88.9 by local artists were typically off of cassette demos before cats became ambitious enough to press vinyl. Our first vinyl was 1996 thanks to Truth Elemental from Brick [Records], and when that was pressed we felt like superstars.

Fakts One: I learned some FCC tricks from the reggae cats to boost up the power of our transmitter so eventually I had people listening live from as far north as Maine. Prestreaming, preweb. At the time, my radio was on and I focused on the indie/underground scene, so I had relationships with everyone as artists. It was the perfect storm.

Rowe: Once we did a handful of events and open mics we were able to convince booking agents and owners that there was a vibrant audience in Boston that was completely untapped. And I think Boston hip-hop artists got more chances to open up shows and headline their own record release parties to continue to build a scene that contributed to a lot of talented acts getting a chance to shine. I credit these artists as their fan bases really made the scene what it was, so without acts like Lif, Ak, Edo G., Illin’ P, 7L & Esoteric, Reks, Skitzofreniks, Fakts One, and many more it wouldn’t have been as meaningful.

Ken Capobianco (music journalist): The hip-hop crowd in Boston was mostly all white college kids. I used to go to the Middle East and Bill’s Bar, and I was a bit older in my early to mid-30s, and it was nothing but people [who were] in the city to go to college. That’s why it was hard to build an audience for a lot of these guys, because the people coming to the show would come and disappear. Really, those crowds were not diverse.

Linberg: O’Neal and I started to hook up with this dude name Rocky LaMontagne who was doing All That! Hip-Hop, Poetry & Jazz events at the Nuyorican Cafe and Lyricist Lounge in New York, so we got connected through him, and started doing All That! together at the Western Front as an open mic night with a live band called Downlow Connection. Great guys. We did that, and then decided to do a battle.

Linberg: There had been battles, both planned and unplanned for events at the Western Front, but we just said we’re going to get everyone because there was a hole in our schedule because of the Super Bowl and the Patriots sucked. It was like, What are we gonna do? The first battle we did was all locals in that Cambridge melting pot scene. Checkmark (of Skitzofreniks); Lif; Akrobatik; Esoteric; REKS; Virtuoso; Big O, who was incredibly dope; and Sage Francis, who no one knew. I think half of them didn’t want to do it, but they felt obligated.

Capobianco: Lif wasn’t into battle rapping. That wasn’t his thing. I covered him from his very beginning. I think he did maybe two, and I don’t think he wanted to be there at the 1999 Superbowl MC battle.

Fakts One: I was honestly surprised at how many “known” MCs wanted in. That made it bigger.

REKS: As far as the battle scene, I feel it was ultra competitive with great talents comprised of young and hungry MCs. The likes of Alias, Ripshop, Mr. Lif, Akrobatik, Esoteric, and Professor Shuman was phenomenal, just to name a few.

Papa D (co-founder of Brick Records): Lif, Ak, and Eso all had records out prior to this event. As for that second generation of dudes—I don’t know if it was a proving ground, but you know, it was definitely the start to their careers. Everyone that was in the battle was doing something in the Boston scene, so it wasn’t all filled with dudes you’d never heard of. But the internet wasn’t popping yet, so it was really dudes you would see at shows, who were trying to record with certain producers.

Linberg: I definitely know that some of the artists were more amped to be there than others. It was the first battle that we had done, and we didn’t really figure out the formatting of it too well ahead of time. When we got there we were like, “Man, we have too many rappers” because basically we put out a call for participants. … A lot of great MCs didn’t make it past the first round because the format was so fucked up. …

The prize was $100. I’m sure some of the people got mad when they lost, but they took it for what it was. It was definitely a “respect” thing.

Capobianco: I remember judging a lot of the battles at that time. … These guys really understood what it took to battle. They weren’t just giving out stupid silly punchlines. It went beyond that. They really understood how to work a crowd and how to weave runs and themes through the short battle.

Sage Francis (MC): [It was] everyone who was doing anything in New England’s hip-hop scene back then.

To the credit of almost everyone I battled, the only thing they knew about me is that I did spoken word and I had a college radio show in Rhode Island. As a radio host, and as a fan of their music, I knew a lot about everyone I was battling. Not only that, but I was battling regularly in Providence for quite some time before the Superbowl MC Battle happened. It was a big deal to me. Not that it wasn’t a big deal to others, but I think I was the one who went full “gym class hero” while almost everyone else was in more of a “we’re all friends” chill mode. I wasn’t friends with them, though. I was definitely an outsider trying to get my name out there.

Fakts One: It was basically a who’s who of Boston rap. Energy building up to it was nuts. Just about everyone in that battle had vinyl out or coming out—reps and egos on the line.

Linberg: It was chaos.

Linberg: A year after, we took it to the Middle East because we needed a bigger room. January 1999 was the first one, and then we did six more battles after that. The last one was the nail in the coffin at Avalon [nightclub] in January 2005. 8 Mile had already come out, so we jumped on that and got JAM’N 94.5 FM onboard as a sponsor, and they agreed to throw down $5,000 as the prize. It was a bigger opportunity, and MCs from all over were flying in for it. We booked KRS-One to perform and be a judge, and it was sold out with like 1,000 people. It was a big show in a big room.

I have to say, looking back, it was a JAM’N 94.5 audience that wanted to see an 8 Mile-style rap battle, and we had these wordsmith sort of underground kids from Cincinnati and other places … so there was a disconnect. So I don’t look at that battle as one of my particular favorites. But all the Middle East ones and the first at the Western Front were all dope to me in their own way.

Fakts One: Sage versus Akrobatik was the best. It was yin vs yang—the two different styles both representative of the division in the indie scene. Nerdy verbose white dude, technical versus street-smart brother/poet. Equally dope but different from each other. And both really freestyled! None of the corny prep rap battle shit nowadays.

Sage Francis: Winning that battle definitely kicked off a lot of major developments in my career, especially since no one really knew who I was outside of the Rhode Island scene. It was a surprise attack on my part and it was definitely an “underdog victory” story, which helped my momentum.

None of this would probably be talked about if it wasn’t for my video camera. The video that is posted on YouTube was from my video camera, which was stolen from me a couple months after the battle. It’s the only footage that exists, so I’d like to thank whoever stole my shit for bootlegging the material and eventually getting the footage into someone’s hands who posted it YouTube many years later. You’re still a steaming pile of shit, though.

This article was produced in collaboration with the Boston Institute for Nonprofit Journalism. To see more long form arts reporting like this, support independent journalism at givetobinj.org.