Matt Siegel, known to most listeners as Matty, hosted the eponymous “Matty in the Morning” radio show on Boston’s Kiss 108 for 41 years.
I first met Siegel in 2017 working as a digital producer for iHeartMedia, Kiss 108’s parent company. Siegel and I worked together to create the first version of his live one-man comedy show “An Evening with Matty in the Morning,” selling out more than a dozen performances at The Wilbur over five years. What began as a working relationship has developed into a friendship, and over the course of two interviews this year Siegel and I discussed his decades of success on the air — and why it all came to an end.
Siegel first appeared on Boston airwaves in 1977 filling in for Charles Laquidara on the legendary rock station WBCN. By 1980, Siegel had made his way to disco mainstay WXKS-FM (Kiss 108), hosting the station’s morning show the following year. For more than four decades at Kiss 108, Siegel’s morning show was consistently the top draw for Boston radio listeners, spawning generations of diehard fans and launching regional events like the annual Turkey Toss. But in 2021, Siegel’s comedic routine started to wear thin on his colleagues, and reports of discontent bubbled up in the media and on the air. In 2022, Siegel’s retirement was announced in a prerecorded message queued up by his former cohosts, Billy Costa and Lisa Donovan.
Siegel, now 74, was inducted into the national Radio Hall of Fame in September. In a wide-ranging interview, the former morning show host reveals what all those years on the radio meant to him, why he left, and whether or not you’ll hear him on the air again.
The following interview has been edited and condensed for clarity.
Hall of Fame induction and Siegel’s best memories on the air
RA: First of all, congratulations on your induction into the Radio Hall of Fame. How does it feel?
MS: It feels great. It really does. That’s a long career on the radio — 50 years, 40 at Kiss. I’m very proud. I’m very appreciative, I’m very thankful for the people who voted for me. I’m thankful for the people who nominated me. Yeah, it’s all good.
RA: What’s your best memory from your years on the radio in Boston?
MS: Oh, there’s so many. The interesting thing about my career is that I consider myself a comic, and so there are lots and lots of laughs. But there were serious moments that I’m particularly proud of. Even when I did interviews with celebrities, it was always about making them laugh. But at the same time, I had a couple of special moments that weren’t funny.
The September 11th attacks happened at the end of my show. When I came on the air the next day, I didn’t do any jokes and I stayed on until 10 o’clock. I stayed on the air the entire day. I told my program director, “I don’t know how the other guys feel about it, but I’ll stay on and deal with it.” I got a letter afterward from the widow of a pilot who died, and she was very appreciative of the way I handled it. I was very proud of that, doing a whole day without jokes. That was special. Another thing that happened that was also very serious was the [Boston] Marathon bombing — same thing. I stayed on the air. I ended up meeting a woman who had lost her leg, and the fireman who saved her life went to visit her at the hospital. Long story short, he came to visit her over and over, it was like out of a movie — they ended up getting married! I officiated their wedding. So that was really, really special to me.
I managed to have Hillary Clinton on with me on election eve in 2016. We just joked around, and I made her laugh. Remember, nobody thought Trump was going to win. Everybody thought Hillary was gonna win. So I just joked around with her, and I was talking to her about how when she was the first lady, there was the red phone right next to her husband. I said, “Are you going to sleep on the other side of the bed now, when you get elected, next to the red phone?” And she said, “They can move the damn phone to my side of the bed!” And I just thought, “this is the Hillary we weren’t hearing.” Everybody thought she was sort of crabby, and I thought “God, if I did all her interviews she would have got elected.”
There’s so many [memories]. In the earlier part of my career at Kiss, we had a stunt guy named Randy, and we did all these crazy stunts. One stunt that got carried away was we put him in the clothes that prisoners wear — the orange jumpsuit. We had him stand in front of the Concord prison. [It’s] really weird that the sweet little town of Concord has a prison right in the middle of town.
RA: Are you referring to MCI-Concord? The historic prison that just closed this summer?
MS: Yeah. So he stood out there and he was waving down cars. I thought that was hilarious until the warden came out and started screaming at him. And then we found out, after the fact, that the guys in the tower had guns targeted on him and he ended up getting arrested. He had to go to jail. He had to do community service. … It was hilarious.
‘The whole woke thing’
RA: You had quite a run, and in those early years you pulled a lot of stunts that I doubt you could get away with today. How else has morning radio changed over the years?
MS: Well, there was the whole woke thing, and I got into trouble toward the end.
RA: In 2021 you made some inflammatory comments about pop star Demi Lovato and their decision to change their pronouns. Can you tell me about that moment?
I wasn’t canceled. But I probably retired a little sooner than I had planned because I wasn’t very good at dealing with some of the woke stuff.
MS: So I interviewed Demi Lovato and she got mad because I was questioning what it means. … I was trying to be open-minded, like, “What does this mean exactly? Are you going to change? Do you not consider yourself a woman?” I was trying to just get to the bottom of it, and she got really mad. I had a producer back then who also got mad at me.
I wasn’t canceled. But I probably retired a little sooner than I had planned because I wasn’t very good at dealing with some of the woke stuff. The Demi Lovato thing got bad. My producer ended up leaving. I made a living out of saying whatever I thought. I was good at that, and sometimes, most of the time, I was joking around. Once in a while I asked a tough question when I was interviewing, and, yeah, it got tougher toward the end. It definitely did.
RA: Do you think there’s a need for that kind of candor on the radio today, or just in media in general?
MS: The thing that was ironic about my career is that I’m a lifelong Democrat. I’m on the left side, politically. I’m an anti-Trump guy, and yet I was criticized for not being woke enough, which I thought was ironic. I’ve been retired for a couple of years, so I can’t speak to what it’s like to be on the air at the moment, but I know it was hard on me [at the end].
Radio beginnings
RA: Before we talk about the end of your career, let’s go back to the beginning. What was it like transitioning from WBCN, a rock station, to Kiss, a disco station?
MS: Well in the rock world, you’re like, stoned. I mean, I wasn’t literally stoned on the air, but you know, you talked in kind of rambling sentences, where Top 40 was much faster pace and all that. And so I basically combined … I think, one of the reasons I was so successful is that I was trying to be a Top 40 guy, but I never got good at it, and I ended up just freewheeling and talking about whatever popped into my head. I was bad at Top 40 in the beginning. But then I got real good because I combined my rock skills with Top 40, and that became my style. So I sounded a lot different than your typical Top 40 jockey. It’s not like I did it on purpose. That’s just sort of how I knew it. I’d never worked Top 40 radio before. It was rock radio. And then I was on a late-night TV show. So I just sort of invented myself.
RA: Did you ever like the music?
MS: I mean, I like ZZ Top. I like Foghat and groups like that, but that wasn’t the stuff that we played. I wasn’t about the music. I had guys like Billy Costa for most of my career who would do the entertainment reports, and then I would just make jokes about it. I couldn’t have done the entertainment report. I didn’t know any of that stuff. This is something I was very proud of — I never went into a song or a commercial without saying something funny. Always. So that was my job. I told the jokes, and then somebody else picked the music. If I had to pick what music to play, we would have had no ratings, because I didn’t like any of the Top 40 stuff, but that was a good deal. We had music directors who picked the music, and I did the jokes in between songs.
Billy Costa, Lisa Donovan, and the new Kiss 108 morning show
RA: The jokes were obviously a core component of your success, and one of the keys to those jokes working on air was having a good right-hand man to riff with. As you mentioned, Billy Costa was that person for a long time. How is your relationship with Billy now? (After Siegel’s departure, Costa and Lisa Donovan were named cohosts of the rebranded “Billy and Lisa in the Morning” show on Kiss 108.)
MS: Billy and I were... Billy and I were best friends, and we had a little falling out. The falling out had to do with something that I don’t want to put in the paper because it was personal. But we did have a falling out, so in the last couple of years I haven’t been on the show or anything, which I was disappointed about, but I’m totally cool with Billy. Billy and Lisa said some really nice things when I got in the Hall of Fame. It happens. But he was a major talent. I couldn’t have done it without Billy and Lisa and the people that preceded them. There’s no way, I mean. I don’t do monologues. I’m either interviewing a celebrity or screwing around back and forth with Billy and Lisa and the folks who came before.
I feel bad, because most people know that I haven’t been on Kiss in my retirement. It wasn’t my plan, I wanted to stay around. But I couldn’t have done it … I wouldn’t have had a career without them and they were very sweet to me when I got in the Hall of Fame. It was a little weird toward the end. But I think what happened right before I retired is that I started [doing] the show from my house in Florida. I wouldn’t say it was a mistake, but it made it harder. Because if we had had that falling out and I was in Boston, we would have talked it out. The fact that I was a couple thousand miles away, we never did work it out. So that’s unfortunate. But, like I said, I’m totally appreciative of his talent. I’m totally appreciative of him saying the nice words he said when I got into the Hall of Fame, and who knows? Maybe down the road, we’ll become friends again; it could happen.
You know, you talk about regrets. The one regret I have is that I didn’t know I was upsetting people.
I kind of burned out toward the end, after 41 years. A lot of it was the woke stuff. … A lot of people got mad at me. You know, you talk about regrets. The one regret I have is that I didn’t know I was upsetting people. I didn’t know. Nobody said anything to me until I woke up one day and everyone was mad at me. So that’s a horrible regret, because the thing is, as far as that goes, I was just being funny. I was just being funny and joking around with my colleagues, and I went over the line. I take total responsibility for that. My whole life, my whole career, was based on knowing where the line was, and toward the end I lost sight of when I was being funny and when I was being hurtful. And so I regret that.
But — and this is the most important thing — I feel really good. I’m honored to be in the Hall of Fame, and totally honored and thankful that my colleagues who were mad at me have forgiven [me]. You know how hard it is to do what I did? I mean, think about it. I had to be funny every day, for 40 years, four hours a day! You go to see a comic, he does the show that he did, 45 minutes, and he does it over and over again. I had to do something brand new every single day! So when I was down in Florida I kind of lost sight of things. But what’s interesting is that, I hadn’t mentioned this before. About five or six years ago I got the idea that I could do a stage show. That’s another thing that I’m really proud of. I did a show at the Wilbur. [The] Wilbur holds a thousand people, and we sold out 14 shows. That’s amazing, because I never did stand-up before. I’m really proud of that.
RA: What do you think contributed to that success? What’s the secret sauce?
MS: ‘Cause funny is funny. Funny on a stage. Funny on the radio. I did a charity event with Charles Laquidara last summer when I was up in Boston, and I had a woman come up to me crying. Like crying crying. I said, “Why are you crying?” And she said, “Because you don’t understand how much you mean to me.” And I subsequently got a lot of comments on Instagram and stuff with people saying that like, for example, COVID-19. I was on the air all through COVID, and a lot of people told me that they felt that I got them through it, that they woke up every day, hearing me doing my funny stuff, and how much it meant to them to the point of tears. It was overwhelming to me. I mean, like I said, I just thought I was just doing a silly radio show. So the connection with my listeners was unbelievable. I mean, unbelievable, because they grew up with me. I’ve met people so many times in Boston, and they said that they felt like they knew me. Because I didn’t do jokes. I just talked, and I talked about my daughters a lot. And people really felt that they knew me because I never had a writer, I didn’t tell canned jokes, I wasn’t Jimmy Fallon. I was just talking about my life in a funny way, and the connection was amazing.
RA: You mentioned ratings. You were always toward the top, if not at the top, of the ratings for Boston. Kiss has not had that same success since you’ve left. Do you have an explanation for the drop off?
MS: Well, first of all, it’s not easy to be number one in a radio market. I was fortunate enough to be born with a skill to get a laugh, no matter what we were talking about. And so this is a hard question for me to answer, because I don’t have any ill will toward my team that went on without me. I’m very proud that we were number one, and if they’re not number one now, I mean, I don’t really follow it anymore. … I feel as though if I were still there we would be number one. But I don’t like saying that, because it makes me sound arrogant, and I don’t mean to be arrogant. I just have a little gift to be able to make people laugh, just sort of born with it. I was the funny kid. I was the emcee of the senior talent show when I was in high school. So I had a little gift, which I’m very proud of. But for the guys that took my place, Billy and Lisa, I don’t wish them ill. I hope they succeed.
Retirement and what happens next
RA: Are there any plans for you to come back to radio?
MS: I’ll tell you what’s tough. For years, I played golf, and it would be like, “Well, I’m lousy at golf, but I’m really successful in my career.” Now, I’m just really bad at golf and nothing else. It’s very depressing. I don’t know, I mean, Billy and Lisa have the show. I’m happy for them. I don’t want to cramp their style. I will say this. I was offered a job to go against Kiss at another radio station — I can’t name it — for good money. And I said no. I don’t wanna go up against Kiss. I didn’t want to do that. I certainly don’t want to get up at five in the morning again. I was very flattered that I was offered a job. But no, I said no. So yeah, I’d like to do something. How much golf can you play? You know I haven’t lost my sense of humor. I would have to have somebody sitting next to me.
RA: If there was the opportunity to go back to Kiss, would you go back?
MS: Not full time. That’s why I turned down that other job. If they were interested in me coming back, I would do that. I haven’t gotten any phone calls. I mean, it’s been a couple of years. I kind of feel if they wanted me, they would have called me by now. But it’s fine. I mean, like I said, I was kind of grumpy toward the end. You have that statement I read when I retired.
RA: The statement that was played on air when you retired wasn’t live, it was prerecorded. Was that your choice?
MS: Well, that’s when that falling out thing happened, and we weren’t very comfortable. I just thought that was the best way to handle it. Everything that I said was true. I had a couple of health issues. I had some pretty serious surgery. I don’t know if you would call it brain surgery, but it was like, [a] pituitary gland thing, that if I hadn’t gotten the surgery, it would have been serious. And I had made the decision to do the show from Florida. I didn’t want to deal with the winter anymore. I was a little disconnected from my colleagues, so it was a little complicated at the time. But I just want to emphasize again, it was a great run, I’m totally appreciative of my colleagues. I couldn’t have done it without them. I take responsibility for pissing some people off. I don’t know anybody that’s lived a whole life without regrets. I mean some. Yeah, I made some mistakes.
Editor’s note: When reached for comment and asked to explain Siegel’s departure, iHeartMedia Senior VP of Programming Dylan Sprague pointed Globe Opinion to the published statement that was played on-air when Siegel retired.
RA: Since your listeners can’t tune in to hear you on the radio anymore, what parting advice would you like to leave them with?
MS: Value your relationships with your family, your wife or husband, and your friends. They’re more important than you know. Tell people you love them even when they’re sick of hearing it. Love your kids. Love your parents. And when you have those bad days, talk it through. You don’t want to wake up alone one day. You really don’t. I know people say, “Born alone, die alone.” Yeah, well, that’s no way to live, you know? You hurt somebody’s feelings, tell them you’re sorry. And if somebody pisses you off, tell them “screw you.” But take your relationships seriously. I’m lucky I have a good solid marriage, and I get along really well with my daughters, and that’s everything.
Rami Abou-Sabe is Globe Opinion’s digital editor. He can be reached at rami.abousabe@globe.com.