Dancer, singer and actor Jim Caruso isn’t just a party waiting to happen. He makes it happen, often at New York City hot spot Birdland and in cabaret spaces around the country.

The North Hills native is best known for “Jim Caruso’s Party,” which has seen him share the stage with Tony Bennett, Ariana Grande, Real Housewives, and folks who just want to share their special skills, some as young as 4 years old.

It’s like “America’s Got Talent” up close and personal, with Caruso and pianist Billy Stritch keeping the mood light, fun and entertaining.

Caruso is back in Pittsburgh on Monday for the Trust Cabaret Series. This time, he brings his “Hollywoodland” show, including Stritch and singer Jane Monheit, for a celebration of “Songs From the Silver Screen” from the 1930s, ’40s and ’50s.

The New York Times gushed about the trio’s “pitch-perfect harmonization” and called it “show-biz heaven.”

Caruso left Pittsburgh for Texas at age 15. When he was a student at Sewickley Academy, one of his early influences was Wayne Brinda, co-founder and producing artistic director of Prime Stage Theatre.

“Jim was high-powered, creative, a top-notch performer and great to work with,” Brinda recalls. “You could see he was going to be successful, and I’m so glad because he deserves it.”

In an email interview, Caruso spoke about his career and how he got his start here:

Q: Was there anything about growing up in Pittsburgh that put you on this path?A: I was lucky to find my way into shows presented by North Star Players. It was considered a community theater, but the production quality was very high.

I got to watch and learn from so many talented people. Priscilla Gardner directed most of the shows I was in, and she was a dynamo. I’d never met anyone like her – pure showbiz, through and through. Wayne Brinda directed me, too, and treated me like a pro. I went to high school at Sewickley Academy primarily because Mario Melodia oversaw the musical theater program. To me, he was a superstar. He had worked with everyone in show business yet understood how to work with young creative minds. I was lucky to have so many mentors at such an early age!

Q: Cabaret is an art form that not every entertainer can do well. Can you talk about the special skill of connecting with an audience?

A: Not surprisingly, performing in a cabaret or night club is nothing like playing a role in the theater. You’d better be comfortable being yourself — or at least a version of yourself — because there is no script and there are no costumes or sets to hide behind.

Every good cabaret artist I’ve seen loves telling stories, either through song lyrics or in conversation. They talk and sing TO the audience, not AT them. Jane Monheit, our “Hollywoodland” partner-in-crime, is a perfect example. Everybody knows she’s a world-class singer. But her fascinating take, as well as her interest and knowledge about the background of her material, is just as important.

Q: Tell us about how “Cast Party” came to be.

A: I threw a party in a now-defunct nightclub. There happened to be a grand piano in the corner, so we all took turns entertaining each other until the wee hours. The next day, the club owner asked if we’d do it every Monday [Broadway’s dark night], since he’d never witnessed such a scene in his venue. We did, gave it a title, and it just kept expanding. We eventually moved the fun to Birdland, the iconic New York City music room we’ve called home [almost] every single Monday for the past 17 years.

A huge reason “Cast Party” has been successful is the quality of musicianship backing the folks who join us on stage. Billy Stritch is certainly one of the finest pianists and accompanists in the world. He’s musical-directed Liza Minnelli and Tony Bennett, among many others, so everyone feels very well-supported when they sing. He’s also a great entertainer in his own right and has been my best friend for decades. Hosting “Cast Party” is like being on a high wire. We never know who will show up for an impromptu performance, so we better be prepared for anything! And that’s part of the fun!

Q: The Trust Series has brought Broadway stars and cabaret icons to Pittsburgh in recent years. What’s the cabaret scene like when you leave New York for cities like ours?

A: Some people think cabaret is a slightly fragile art form. But everywhere we go, we find a lively scene and a renewed interest in the Great American Songbook. Everyone’s taste is different, of course, but I can’t imagine anyone not being entertained by a great singer performing solid material and telling interesting stories.

Q: Tell me about the type of acts that come your way.

A: At “Cast Party,” we’ve been privy to spontaneous performances by Tony Bennett, Ariana Grande, Jon Bon Jovi, Natalie Cole and Carol Channing. Liza Minnelli announced her divorce at “Cast Party.” Martin Short and Paul Shaffer tried out material for the following night’s Letterman show. Donny Osmond made me an honorary Osmond Brother. Michael Feinstein filmed us for his PBS Series. The “Real Housewives of New York City” sang and brawled on our stage. We’ve watched Miss Americas, 4-year-olds, ex-Village People, hula dancers, contortionists, has-beens and hopefuls.

With “Cast Party,” and certainly with “Hollywoodland,” I can’t believe that I get to do what I do for a living. I’m happiest in front of a packed house when the energy is high, everyone is laughing and the music is swinging. It feels like there couldn’t be a problem in the world. We all get to share such a happy experience.

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First Published: February 7, 2020, 5:42 p.m.