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Three Local Rappers Tell How They've Worked To Attain Measure Of Success

By ERIC R. DANTON

July 25, 2010

Chris Webby is a prolific mix-tape maker.

P.E.S.O. headed west for a few years.

Tone Benjaminz hones his craft in the studio.

All three are Connecticut rappers with a common goal: building a following for their music.

Creating an audience is a necessity for any career-minded artist, one made more challenging in a genre where live performance is often a secondary consideration. The template for rappers trying to establish themselves is different from the one their rock 'n' roll (or blues or country) counterparts have traditionally followed: Instead of building a fan base through relentless gigging, winning over crowds a roomful at a time, hip-hop tends to flip the script by trying to establish buzz that will attract an audience.

"The rock bands, they love to go out and play and perform for people. Sometimes the hip-hop crowd, they're in it for something else," says DJ Buck, program director on WZMX-FM (Hot 93.7), who hosts hip-hop showcases on Sunday nights at the Warehouse in Hartford. "Rappers, they want the reward at the end of the tunnel. They want to be on the radio."

If radio play is the Holy Grail, it's equally elusive. But there are plenty of other ways to be heard in the digital era, when it's easier than ever to record and release music on your own. That's the approach Webby, P.E.S.O. and Benjaminz all have taken.

"I don't ever chase radio," says P.E.S.O., 31, a Hartford native. "I make what I want to make, and if radio embraces it, cool. If not, I'll live."

Webby hasn't needed radio. Now 21, the Norwalk native started rapping in middle school, engaging in freestyle battles with classmates and rhyming off the top of his head at social functions in high school. After establishing a presence online via Facebook, YouTube and Twitter, he started performing at open mikes and friends' parties and giving away his music for free on mix-tapes, CD compilations of songs he's recorded. He's released three mix-tapes so far, with a fourth on the way.

"Probably the one after that I'll put out on iTunes," Webby says. "But you have to give your [expletive] out for free. There's so many people walking around trying to sell their CDs, and I used to do the same thing. But at the end of the day, what's more important — I've got $5 in my pocket, or someone's driving home listening to my music?"

Although he has yet to make any money on recordings of his music — brash, funny songs about his attention deficit disorder and fondness for weed — Webby says all of those free mix-tapes have led to paying gigs and inquiries from record labels.

"Honestly, I'm making a decent living off it now," he says. "I haven't had radio play yet; I'm just doing this off shows and a grass-roots fan base at this point."

P.E.S.O. tried a different approach to building a local following: He left.

After scrapping around the Hartford-area scene for years, performing at open mikes and block parties and trying to run a fledgling record label, P.E.S.O. was discouraged by the lack of mutual support among would-be rappers here.

"It's the whole crab in the barrel mentality: No one wants to see anyone come up if they're not coming up," he says. "Everyone has a friend that's doing it, so their first thought is, 'Why would I support you when my boy John up the street is doing the same thing?'"

Eager for a change of scenery, P.E.S.O. moved to Los Angeles. There, he says, he was performing regularly in clubs when he ran into a disc jockey he knew from Hartford at a Grammy party. The DJ returned home to talk him up on the radio.

"When you start doing things outside your market, and it seems bigger than it really is, it'll get back home, and people will respect you more, at least from what I've seen," says P.E.S.O., who has since moved to Manchester and self-released "The Air," an album of what he calls "alternative hip-hop" songs.

Like Webby, P.E.S.O. stresses the importance of social media as a promotional tool, regardless of physical location.

"We're in a digital age, so you've got to have a strong Internet presence," he says. "You have to have the YouTube thing going on, Facebook, Twitter, all the new social-networking sites."

Along with freebies and social media, having confidence is key in building a following, the rappers say — especially having the confidence to be real, even if that means avoiding the usual rap clichés that have served others.

Benjaminz, a "thirtysomething" Hartford rapper, came up in the '90s, when gangsta rap was at its height. Fifteen years later, though, he's ready to hear something else.

"We've seen the drug deals go down, task-force round-ups, shootings in the streets and clubs," says Benjaminz, who has collaborated with other area rappers and worked on a solo career that last year yielded the self-released "Same Game, No Pressure." "We've seen the scantily clad women and fast money. Been there, done that. We're adults raising kids now. Where's the rapper fed up about long lines at Wal-Mart?"

Even Webby — who's serving three years' probation for driving the getaway car after his friends robbed a drug dealer last year at Hofstra University on Long Island — steers clear of his run-in with the law in his music.

"If I talk about it, it's about how everybody makes mistakes," he says. "Dude, I rap about weed and girls and a lot of clever metaphors and cartoon references from when we were little kids. I really speak to my generation, kids who grew up in the '90s and late '80s. I talk about [expletive] that they can relate to. That's No. 1 Webby rule right there: Be yourself. If you're not being yourself, people will see through that eventually."