Mark Parenteau, 66, longtime WBCN-FM afternoon DJ

Mark Parenteau in 1978. Globe Staff/File

For years they lined up to speak with Mark Parenteau on his WBCN-FM afternoon show — rock stars, comedians, politicians. Like his DJ colleagues who made the station a must-listen throughout New England, Mr. Parenteau knew his music, but it was his lightning, biting wit and unexpected questions that turned wary interview guests into immediate friends the moment he switched on the microphone.

“Mark had real conversations,” said Steve Strick, a former assistant program director and music director at WBCN. “He asked everyday questions. He would get them to talk about their lives outside their performing, so it made them more human and relatable to the audience.”

At times it seemed as if Mr. Parenteau was at his best when circumstances were at their worst. One time a record company executive called ahead to caution that Brian Wilson of the Beach Boys “was out of it,” recalled Charles Laquidara, who was the station’s morning personality. “Mark did one of the best interviews ever for Brian Wilson and ’BCN, and he saved him,” Laquidara said. “No one was a better interviewer than Mark Parenteau. When he did interviews, he would bring out the best in people.”

Mr. Parenteau, who helped write a chapter in Boston radio history during his two decades at WBCN, died Friday in Massachusetts General Hospital of complications from surgery. He was 66 and lived in Worcester.

In 1997, Mr. Parenteau and WBCN parted ways and he took a radio gig in New York City before heading to Washington, D.C. Mr. Parenteau was working for XM satellite radio when he was charged in an 18-count indictment. He pleaded guilty to one count of second-degree sexual abuse for an incident involving a 14-year-old boy, the Washington Post reported in April 2004. The Post also reported that the plea agreement was reached as prosecutors grew concerned about inconsistencies in the accusers’ accounts and that many facts in the case remained in dispute. Mr. Parenteau was sentenced to three years in prison. “I want to make amends,” the Post quoted Mr. Parenteau as telling the judge. “I want to stay sober . . . want to pick up the pieces. . . . I’m truly sorry for the entire affair, and I hope I can prove to the court that I am a responsible person.”

After being released, Mr. Parenteau returned to Massachusetts, where at times his conviction went unmentioned when he surfaced in news accounts. That was the case in December 2014, when he went to hear Bob Seger and the J. Geils Band, two acts whose careers he helped during his DJ days in Detroit and Boston. “It was probably the last concert I’ll ever go to,” Mr. Parenteau, whose health was failing due to spinal stenosis, told the Globe afterward.

Born in Worcester, Mr. Parenteau was the older of two siblings. His father, Paul, was an electric lineman. His mother, the former Lorraine Crean, helped steer her first-born into radio. She worked, sometimes on-air, for a woman who had a radio talk show in Worcester. When Mark was around 7, they had him record a commercial. “He made the commercial and he was smitten by it,” said his brother, Barry of Millbury.

Mr. Parenteau began his radio career while still in high school. John Garabedian, who years later would work with Mr. Parenteau at WBCN, was hosting a morning show at a Worcester station in the 1960s, “and I’m in the studio one morning and I turned around and there’s this tall, skinny kid.” It was Mr. Parenteau.

“The thing that made Mark stand out was his passion and his entertaining,” Garabedian said. “He had that even then. I noticed in the first hour after I met him that he had a sense of humor second to none. I would put him up there with the top comedy writers.”

Garabedian added that Mr. Parenteau “was hysterical. People thought he was funny on the air. He was four times as funny off the air. Everything that happened, he would come out with a wisecrack that was really brilliant.”

Mr. Parenteau started at WORC-AM in Worcester, moved to Lowell station, and then got his first big-city break in Detroit. While there he married. His wife, Gail Parenteau, was working for a concert promoter, he recalled in an interview with EVE radio that is posted on YouTube.

In Detroit, Mr. Parenteau first interviewed the members of Aerosmith and became friends with singer Steven Tyler and guitarist Joe Perry. His friendship with the two remained strong and once after the band broke up acrimoniously, “I was an integral part of talking Joe into becoming friends with his brother Steven again,” Mr. Parenteau said in the EVE interview. “They acted like they hated one another, but I knew they didn’t. It’s sort of like when brothers act like they hate one another. They really don’t hate one another. They’re still brothers, you know? So I got them back together again.”

Mr. Parenteau returned to Massachusetts in the 1970s to work at WCOZ-FM and then jumped to WBCN.

“He was one of the most amazing talents I’ve worked with in 40 years of radio,” said Tony Berardini, a former WBCN general manager. “The guy could interview a stone and make it sound interesting.”

Mr. Parenteau also was known for pushing the boundaries of what DJs could say on air. One of his signature phrases was “lick me” – often stretching out the “i” for maximum effect. “I never go against the FCC rules,” he told the Globe in 1992, adding with smile and a raised eyebrow: “Maybe I say things that make them wish they had more rules.”

Along with interviewing rock stars such as John Lennon and David Bowie, Mr. Parenteau spent years giving radio time and career boosts to comedians such as Anthony Clark and the late Sam Kinison, whose intense presence was a lively counterpoint to the radio host’s during their memorable on-air conversations. “Mark became the honorary dean of Boston comedy,” said Carter Alan, a former colleague who wrote “Radio Free Boston: The Rise and Fall of WBCN.”

A funeral Mass will be said at 10 a.m. Saturday in Our Lady of the Angels Church in Worcester for Mr. Parenteau. His marriage ended in divorce and his brother is his only immediate survivor.

Mr. Parenteau was so popular that his on-air sparring with Boston City Councilor Albert “Dapper” O’Neil over matters such as the decency of art exhibits and the noise level of boom-boxes became de facto comedy routines. Mr. Parenteau would splice the councilor’s comments into a pulsing beat and introduce it as “The Dapper Rap.” O’Neil, meanwhile, insisted that the DJ’s barbs brought him more support from conservative voters.

Nearly 20 years after leaving WBCN, Mr. Parenteau regularly ran into people who would hear him speak — in a bank teller line, for example — and immediately recognize him. “It’s like the voice just hits people sometimes, and they hear it and it brings back all those memories,” he said in the EVE radio interview.

“It was a big deal, but I didn’t think of it that way at the time. It was just what I did,” he said of his WBCN tenure, adding that “you’d hit that switch and suddenly you were talking to like 3 million people in six states around New England. It was very powerful, you know?”