Thanksgiving is the best holiday on the calendar. It’s a non-denominational, non-political, non-threatening time when we ponder things for which we are most grateful. The only thing that can go wrong at Thanksgiving is gastronomical in nature. Defying every cliché in the book, this editor is most grateful this year for his mother in law. And here’s why.

 They say that when you tie the matrimonial knot, you don’t just marry the person; you marry the whole family. For some people, this might present a few problems, but for me that has never been a concern because when I married my wife, I hit the in-law jackpot. Not only did I marry a beautiful, brilliant and talented woman, I also acquired two super new (well, slightly used) brothers and another father (RIP, Barry), a trifecta of Irish raconteurs who kept me in stitches with their tales for years.

The biggest surprise of all, however, was my mother-in-law. Mother-in-law jokes have long been the stock in trade of every standup comic from Henny Youngman to Joan Rivers, but they’re wasted on me. Why? Because my mother-in-law OPENED for Joan Rivers, that’s why! My mother-in-law is the one who TELLS the jokes around this family!

On a day like today, when we are asked to ponder things that we are thankful for besides the heaping mounds of food on the table, I can easily point to having Carol as my mother-in-law, confidante and kindred spirit. So, without further buildup, I would like to introduce you to Carol O’Shaughnessy, Boston’s First Lady of Cabaret or, as Joan Rivers once described her, “the best singer in my price range.”

As Carol nears her 79th birthday, she is still hitting the stage, with her musical director, Tom LaMark, an occasional orchestra, and a kit bag of Great American Songbook nuggets as well as her own comedic riffs and gags (including longtime staples like Mama Scugliacchi and Hardhatted Hannah) that have been knocking ‘em dead and drawing crowds since the early days of her career as a member of a Gilbert & Sullivan troupe at Arlington High School (Mass.), a singing waitress at Romie’s in Danvers, a regular on the cabaret circuit in nearly every state on the Atlantic Seaboard, as well as in Texas, Arizona, California and the Caribbean. She’s played all manner of venues in Provincetown, Worcester, the North Shore, the South Shore and, of course, as one of the pillars of the Boston entertainment scene. Who knows, she may have also played at your wedding reception or bar mitzvah.

Earlier this month, Carol premiered The Rat Pack…And Me, a new production, written for her by veteran playwright Jack Neary, at Club Café in Boston—one of the Hub’s longtime keepers of the cabaret flame. She wants to take this raucous production to a bigger stage, a more expanded and theatrical production. And she will be playing in New York City, at Don’t Tell Mama, on Dec. 9 at 7 p.m. Did I mention that she’s nearing her 79th birthday?

Oh Carol O’, you are the best.

“This Joint Is Jumpin’”-Carol O’Shaughnessy

I recently tracked her down in her snug (yes) mother-in-law apartment attached to one of her son’s houses in Arlington, Mass., to give her the PKM third degree.

PKM: Where did you grow up and at what point in your childhood did you know you were going to be a singer?

Carol O’Shaughnessy: Arlington, Mass. I knew I was a singer by the time I was 3. My grandfather played the piano and we’d go into Boston to visit my grandparents at their apartment on Huntington Avenue. There was a little area as you came into the apartment, a sort of foyer and that became my stage. I’d perform from there, with my mother, father and grandmother all sitting in chairs or on a sofa and my grandfather playing the piano. It made them laugh.

PKM: What were you singing at such a young age? Surely nothing too elaborate…

Carol O’Shaughnessy: Stuff from the Great American Songbook, music that was popular from the 1930s and ‘40s, the music my grandparents loved. I thought everybody listened to this and sat around singing like this.

PKM: When did you learn that not everyone actually did do that?

Carol O’Shaughnessy: I never paid much attention to what other people thought. It just all seemed very normal to me so it probably wouldn’t have mattered what anyone else thought. I remember in the 1st or 2nd grade a teacher asking if anyone in the class wanted to sing. My hand shot up. So did Bobby Hyatt’s hand. We ended up singing a duet.

I took dancing lessons from the ages of 8 to 13. The teacher asked me if I sang. I said sure, so she worked up a dance routine to go along with the song “In the Cool Cool Evening.” When I performed this song and dance routine, people said to my mother, “I didn’t know Carol Ann could sing?” and she said, “Neither did we.” She didn’t see it as a big deal since I had been doing it for so long. I got a big laugh out of it. 

PKM: What were the singers, or voices, that turned your head as a young girl on the radio?

Carol O’Shaughnessy: Not on the radio. I would buy 45’s and play them endlessly on my little record player. I’d go down to a shop in Arlington and buy a new 45 single every week; sometimes they’d have a special compilation record on sale. I’d buy Sinatra, Sammy Davis Jr., Dean Martin, Ella Fitzgerald, Johnny Mathis, not any of the bebop stuff.

PKM: What about rock ‘n’ roll?

Carol O’Shaughnessy: I danced to rock ‘n’ roll at the dances they held at the Immaculate Conception Church Hall in Cambridge. They’d have a live rock ‘n’ roll band there, and all the cute boys would come. I may have bought a few Chuck Berry 45’s but most of the rest of it didn’t grab me. It had no lyrics, at least not any I wanted to sing. I wanted to sing adult songs, you know, songs that were popular with the adults, like Perry Como, Eydie Gorme, Doris Day. I loved Perry Como’s TV show. As an only child, you grow up with adults and you learn to like adult things.

PKM: Was there ever one singer you just totally wanted to be? Garland? Sinatra? Rosemary Clooney?

Carol O’Shaughnessy: I never really wanted to be any of the singers I heard. I was raised by a mother who told me ‘Don’t be afraid to be different.’ I greatly admired women singers like Eydie Gorme and Caterina Valente. I was mesmerized by Caterina’s talent.

I also always loved theater and in junior high school I had a teacher I adored, Donald Hermance. He loved Doris Day, so I learned one of her songs so I could sing it for him, “Secret Love.”

PKM: How did you get involved with Gilbert & Sullivan?

Carol O’Shaughnessy: When I got to high school, 10th grade, I got involved in sports, tried out for cheerleader, meantime also involved with music. I had a music teacher in high school named Ludvig Hassler Einzig. Mr. Hassler to me. Hass to everyone else. I was Miss Pascarella. He was instrumental in getting me involved seriously with music. For two years, I was in his Gilbert & Sullivan operetta group. Later, when my three children were little, I was involved with another group that Mr. Einzig directed. It was called the Winchester Staff and Key Society.  I did a whole bunch of Gilbert & Sullivan productions with that group. I used to drag the kids with me during rehearsal. I think they still hate me for that! 

But, getting back to high school, I was also one of six chosen to be in the Harmonettes. It was a big freakin’ deal to be in the Harmonettes.

In 12th grade, the after-school curriculum, for music, became part of the regular curriculum, which meant I now had to choose between music or the stenographic course for first period. I chose stenography because I was told I needed to have a skill to get a job. It actually, in the long run, was really useful but at the time I was heartbroken. So was Mr. Hassler. He had tears in his eyes when I told him. He said I was talented and was distraught that I’d just walk away from singing. That was the first time I felt like I really had something to work with.

PKM: What was your first paying gig as a performer? Was that the singing waitress job at Romie’s?

Carol O’Shaughnessy: At 16, my first paying gig was as a Harmonette. We got $5 and a rhinestone pin for playing at the Winchester Country Club. But after that I don’t think I got paid for a professional gig until after maybe 1970, working with G.B. [general business] bands at weddings, Elks Clubs, bar mitzvahs and the like.

PKM: How did you find out about Romie’s?

Carol O’Shaughnessy: I discovered Romie’s when I went on a date there. I told myself, ‘I’m going to work here someday’. In my first audition, I fell flat on my face but in 1977 or’78, I nailed it and worked there for two years. There was a really talented staff, many went on to Broadway. I was working a full day job at Digital, getting off at 5 and having to show up at Romie’s by 6, with the dinner service starting at 7. First show was at 8:30. We worked hard, two shows a night. I started two nights a week, Fridays and Saturdays and then, after I quit my job, it was four nights a week My section of 30 customers became my showroom. That’s when I learned how to patter with an audience.

PKM: What about your long connection to the club scene in Provincetown?

Carol O’Shaughnessy: Provincetown work grew out of working at Romie’s. Two of my [male] co-workers had a cabaret act and asked me to join them one weekend at the Male Box, a gay cabaret club in Worcester. I got up on stage to do one song and could not get off for the next twenty minutes. It was a total fluke. The owner of the club hired me on the spot, on Feb. 29, 1980. Everything opened up after that because I began playing the gay circuit. Without the gay community, I wouldn’t have had a career.

PKM: What were some of the clubs in Provincetown where you played?

Carol O’Shaughnessy: In Provincetown, there was the Post Office Cabaret and the Pilgrim House, the Pied Piper, Crown & Anchor, I’d just go where the money was. I went on the road in 1980 and stayed there for the next ten years. Maine, Vermont, New Hampshire, Connecticut, New York, New Jersey, DC, Florida, Texas, Arizona, Los Angeles, Washington. Some gigs lasted a couple of nights, some were 3-week engagements. In Boston, the regular venues were Buddy’s on Boylston Street and Club Café, which opened in 1983 and is still where I perform regularly.

PKM: I know you were nervous for weeks about this latest show at Club Café, The Rat Pack…and Me. It was a great success, as we all knew it would be. Even with all that pre-show anxiety, when you get up on stage, do the fears disappear? What makes them go away?

Carol O’Shaughnessy: The minute I see an audience, some of the anxiety disappears. I was nervous [about The Rat Pack…and Me] because it was a different format, a tightly scripted show, with seven musicians in the orchestra. Was it perfect? No. Did the audience know this? No. We got two standing ovations or, if you prefer, ovulations. The buzz from the show has been amazing. I want to do it again in a theater.

PKM: Was there ever a time when you came out on stage and realized 1) the audience was dead; 2) the venue was wrong; 3) you were bombing? How do you light a fuse under such an audience or, failing that, politely cut your losses and get the hell out of there?

Carol O’Shaughnessy: I’ve never bombed, really. But I’ve played to small audiences. I give the same effort if there just one person out there as I would to a full house. When I walk off the stage, if I think, ‘I did my work’, then I can live with that. Tom [LaMark] often tells me, ‘it’s just another gig, Carol’ I deal with it. The old showbiz cliché ‘You’re only as good as your last show’ is mostly true.

PKM: Who were some of the more memorable characters you’ve shared the stage with over the years? You’ve mentioned Tiffany Jones a few times in the past. What was his/her act like?

Carol O’Shaughnessy: Tiffany Jones’ real name was Ken Whitehead, a beautiful guy and brilliant. He would enter the Crown & Anchor in Provincetown on roller skates, dressed in a full habit, lip-synching “Dominique” by The Singing Nun. And he could really skate! And the finale of his drag act was equally brilliant. He’d lip synch to Charles Aznavour’s “What Makes a Man a Man” while pretending to be in front of his mirror at home, getting undressed. He’d remove layer after layer of clothes down to his jockey shorts, to illustrate the transformation from woman to man. The whole time he would be talking to the audience, telling stories.

Ken Whitehead/Tiffany Jones being interviewed on a local TV station:

Ken, sadly, was one of the first of the drag queens to die of AIDS-related illness, in the early 1980s. We lost about 13 drag queens this way in a very short amount of time. It was so tragic. We kept a permanent tip jar circulating to donate to AIDS research and medical bills. That was such a tough time. It was in the earliest days of AIDS when we were just beginning to understand what caused it and how to prevent it. There’s a sense of déjà vu, I think, in the gay community now with the COVID outbreak.

PKM: It strikes me, talking to you in this way, that you have been just as enamored with the theater as you are with singing. Is it just the lure of the stage and the spotlights that is a magnet for you?

Carol O’Shaughnessy: I didn’t take many voice lessons and never had any acting lessons. But I just knew it was my real calling from an early age. And I keep doing it because I love it. And it makes people happy. It makes them laugh, and laughter is oxygen to a performer, quite literally, you know.

“Happiness is a Thing Called Joe”, Carol O’Shaughnessy-voice; Tom LaMark-piano:


For more about Carol O’Shaughnessy, go to:


You can hear selected cuts from her CDs here:


Carol will be at Don’t Tell Mama on Dec. 9, at 7 p.m., 343 W 46th St, New York, NY 10036

212-757-0788 https://www.donttellmamanyc.com/