He wasn’t around to experience it firsthand, but Rich Terfry figures 1957 was one of the most exciting years of the last century. It’s hard to argue with the guy who records and performs under the name Buck 65. After all, a quick scan of Wikipedia’s page on the events of that year yields the knowledge that it was when Jack Kerouac’s On the Road was published and his fellow Beat writer Allen Ginsberg faced obscenity charges for Howl; Elvis Presley made his third appearance on The Ed Sullivan Show and was filmed from the waist up so as not to send Middle America into a sexual frenzy; the U.S.S.R. won the first round of the space race by launching Sputnik 1 and 2; and in Liverpool, the Cavern Club opened and John Lennon met Paul McCartney for the first time.

Those are a few of the events that inspired Terfry to write the most recent Buck 65 release, Situation. The album, which takes its name from the Situationist International—a group of political and artistic avant-gardists founded in, you guessed it, ’57—explores the rise of rock ’n’ roll, pornography, teenage rebellion, and other forces that emerged to shake the western world out of its grey-flannel complacency.

“It was like an upsetting of the comfortable establishment,” Terfry says, reached on the road in Hamilton, Ontario. “Before that, in the postwar, baby-boom era, with the creation of the suburbs and stuff, people were getting real comfortable and real happy and had their neat haircuts and white picket fences and so on. And then all this stuff started to happen that upset that comfort, whether it was in people’s own back yards or halfway around the world or whatever else, and a lot of people got real scared.”

Terfry, who was born in Nova Scotia in 1972, says he’s inspired by the artists and agitators who tear down old notions and create something new on their foundations. The well-spoken musician is something of a maverick himself. He is most often categorized as a hip-hop artist, a classification borne out by Situation’s jazz- and funk-inflected beats (courtesy of producer Paul “Skratch Bastid” Murphy) and tongue-twisting rhymes. Past efforts, however, have found Terfry spiking his music with shots of folk and blues. He notoriously went on record in 2004 with the comment that he had grown to hate hip-hop. He quickly recanted that, but his relationship with certain elements of the rap world remains tense.

“If what I’m doing, as far as hip-hop goes, upsets anybody or whatever the status quo of that is right now, that’s one thing that I don’t have any problem with whatsoever,” Terfry says. “I just think it needs to be done. And if it doesn’t need to be done, like, across the board—which I’m not suggesting—at least having it happen off in one corner somewhere keeps things interesting, I like to think.”

Spoken like a born-too-late member of the Beat Generation.

Buck 65 performs at the Commodore Ballroom on Wednesday (May 7).