Jim Caruso on the Magic of Connecting to an Audience

“Have I told you about…”

Coming from anyone else, those are just words. But when it’s Jim Caruso who’s doing the asking, you pay attention.

There was the time Bono showed up to Bemelmans Bar at The Carlyle Hotel during he and Billy Stritch’s set. (“Billy was just starting to play ‘I’ve Got You Under My Skin,’ which Bono had recorded with Sinatra. All of a sudden, Bono was sitting on the piano bench harmonizing into the mic. Three days later, I called Billy and left the following message, ‘This will probably be the only time I will tell you that we are in Rolling Stone this week.’”)

There was the time The Real Housewives of New York paid him a visit at Birdland. (“The ‘Housewives’ showed up with a gigantic camera crew. It was come-what-mayhem! They all ended up singing, and Billy and I provided backup for Countess LuAnn de Lesseps, which made Pinot-swirling Ramona Singer livid. She began a Ramona-coaster of insults, hinting that LuAnn had personally hired Billy to play for her. LuAnn sniped, ‘He’s Liza Minnelli’s accompanist, you cow!’ which turned into the Cast Party Quote of the Year!”)

And of course there’s Cast Party at Birdland, an evening he calls “the Ellis Island of Open Mic nights…at some point, they all come through the gates!” (“One of the most bizarre nights was the night that Betty Comden walked in the room. She was all in black and diamonds, all alone. She looked spectacular. She walked in, watched and clapped and cheered for everybody, very low key. At one point, she motioned for me and Billy to come over and she asked if it’d be alright if she sang something. This is an icon of the American theatre. She sang ‘100 Easy Ways to Lose a Man’ from Wonderful Town, and people were crying because of the historical value of it.”)

He’s been one of BLEEP’s biggest cheerleaders from early on and I sat down with him to talk about life today, the thrills of performing at The Carlyle Hotel and at Birdland, and why he is so in love with connecting to an audience.

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Photography by Christopher Boudewyns

You’ve been performing in weekly shows in New York for a long time. How do you keep it from becoming stale?

With regards to what Billy and I do at The Carlyle Hotel, it’s different every single week. When we first got the job, we pictured ourselves being the new wacky versions of Bobby Short so we learned all of this Rodgers and Hart and Cole Porter material. We did that for a couple years but we figured out that’s nobody’s nostalgia anymore. Time marches on. As much as people were smiling, snapping along, and enjoying what we were doing, the minute we’d get a request for something a little more contemporary like Sinatra or Sammy Davis Jr., the whole room brightened up. Our audience isn’t in their 80s and 90s. They’re in their 40s, 50s, and 60s. So we started taking many more requests. We will read the songs from our cellphones and do whatever we can to make that happen. They make crazy requests, funny requests, and serious requests and we will try almost anything. Sometimes it’s not successful but they laugh along. It’s become a big party. I wasn’t expecting that at that particular job.

Cast Party at Birdland is the same thing. It’s absolutely different every week. We never know who is going to come through the doors. It could be Broadway stars, people who write songs who are never going to be Sondheim, and everything in between. It’s kept fresh just by the fact that it’s a shock every week.

Wasn’t Tony Bennett there this past week?

Yes. He was.

I read one of his books a few weeks ago and was surprised by how many times he mentioned Birdland in the book.

He really loves the room. I have a quote here that says, “To work at Birdland means you’ve really arrived on the scene.” Herbie Hancock said that. There are certain places that have good energy because of all that’s happened there. Radio City is one, The Palace Theater is another, and to me, Birdland is that too. The music in those walls is palpable and to have the opportunity to work in a place like that, I feel so lucky.

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Photography by Christopher Boudewyns

Do you have a favorite memory of your time at The Carlyle? I’m sure there have been so many one-of-a-kind moments.

So many. When someone like Bono is sitting in the corner while you’re singing standards and he walks by and puts his hand on your hand, which is on the mic, and says, “Thank you for a great night,” those are surreal moments. But I don’t want to make it sound like it’s the starry stuff that makes it special. The Carlyle is a unique space in that it’s such a New York insider place but it’s also packed with tourists.

Did I tell you about the night when six priests came in while we were singing? There were five men and one women, all in black and had the white collars. They walked right by me in the middle of the song and after the set, I went over to meet them. They were so casual and nonchalant as they said they were just out having a nice time drinking martinis and enjoying the music. I’ve never seen six priests in a bar. It sounds like the beginning of a terrible joke. They work up the street, two were gay, and they were absolutely extraordinary people to talk with. Such a New York experience; talking to six priests at The Carlyle.

It really does speak to the commonality of music that connects us across the spectrum.

Yes. They came because there’s music and it lifts people’s spirits and I’m sure their spirits need to be lifted a lot because of all they have to deal with. I think that’s why we all gravitate toward it.

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Photography by Christopher Boudewyns

We’ve talked a lot about Cast Party but do you have a similar story about making connections at Birdland?

Did I tell you about the wedding party? A newly married couple decided that instead of a reception, they were going to Cast Party at Birdland. They made a reservation for 30 people and they filed in just as we started singing. People were very dressed up, then the groom came in wearing a tux and the bride came in wearing her wedding dress and veil. I asked them, “What is happening?” and they said, “We just got married! This is our favorite thing! We love it here and we come here once a year from out of town.”

We sometimes forget that for a lot of people, Birdland is a big deal. Last week, a guy from Sweden came up and told me they’ve been coming to New York once a year for fifteen years and they always stay over on a Monday because Cast Party is their favorite thing in New York. We are used to just doing our thing up there but you just don’t realize that out in the audience, there are people having the time of their lives. It’s this cool, weird, New York thing to do and that is thrilling to me.

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Photography by Christopher Boudewyns

You toured with Liza for years but apart from her, you’ve worked with so many of the greats. Many of them even call Birdland their home as well. In your opinion, what is something they all have in common?

I’m attracted to performers who love to connect with an audience. A lot of performers are very shut off. They stand on stage, close their eyes and sing. I find that truly dull. When I experience people truly connecting with the crowd, I’m dazzled by that. That’s the connecting tissue it seems.

What makes you happiest in the world?

One of the times I’m happiest is when I’m standing off to the side of the room, something great is happening on the stage, and people are looking at the stage with wonder and rapt attention. I think, “Wow.” It’s about the connection. I live for connecting with people in that way.

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Photography by Christopher Boudewyns

Interview by Ryan Brinson
Photography by Christopher Boudewyns
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