A Wall Street attorney by day, a captivating crooner by night. What inspired Marty Geiger, at age 50-something, to pursue his later-in-life dream of becoming a cabaret singer—despite the fact that he’d rarely sung, even in the shower, for more than 30 years?

Geiger grew up in Westchester County, New York, the second of four children and, he admits, the one who tended to get the most negative attention. “I just wasn’t involved in the ‘right’ activities—which, to my parents, meant sports,” he says. “I always felt I had plenty of natural athletic ability, but I was just not interested.”

His parents did notice, however, that their son had an affinity for music. They convinced 8-year-old Marty to try out for Name That Tune. Geiger explains: “Unlike today’s TV game shows in which you press a buzzer if you know the answer, in Name That Tune, contestants had to dash across the room and be the first to touch a punching bag suspended near the moderator’s podium. I knew the songs, but I didn’t run fast enough.” Oh, the irony.

When Geiger was sent to Phillips Academy several years later, he knew his parents secretly hoped Andover would somehow turn him into a hockey or soccer star. Instead, Geiger took some piano lessons and got involved with theatre. In the fall of his senior year he wrote, directed, and produced a short play. “One of the saddest times of my life was the weekend A Saga of Mr. Goodbe was first performed in the DramaLab,” he recalls. “I was so proud and excited—yet my parents chose to attend my older brother’s soccer game instead of coming to see my play.”

For the next several decades Geiger’s interest in music kept taking a back seat to other more pressing matters. He attended the University of Rochester, earned a JD degree from NYU, and in 1974 joined the bond counsel firm Hawkins, Delafield & Wood LLP in New York City, where he is currently a managing partner. Geiger provides legal counsel to nearly 200 public school districts in New York State in connection with borrowing money for the issuance of tax-free bonds—usually to build new schools, libraries, and athletic facilities.

On or about his 55th birthday, Geiger took stock. Life had been very good to him. He had a great family, a wonderful wife, plenty of friends, a nice house, and a job that he loved. But something bothered him. Something was missing.

“I’d always kind of had this voice singing in my head, but, due to a certain shyness and the lack of encouragement from others, I’d rarely sung out loud,” Geiger explains. “I saw my clients retiring to pursue their hobbies and interests, but I had to keep on working. Suddenly it dawned on me. If not now, when? I signed up for voice lessons the next day.”

At first he was discouraged. The vocal exercises were tedious, his throat hurt, and he hated the lip vibrations. But Geiger persevered. In the course of the next two years he worked with a couple of different coaches, found his natural vocal range, and gained much-needed confidence performing in front of his peers. In early 2006 he was finally ready to entertain a real audience.

“Cabaret was definitely the place for me. The setting is small and intimate, you can be your own producer—and no auditions are required,” he says with a laugh.

In March 2006 Geiger first met with his director, Lina Koutrakos, to discuss possible songs and theme. “It was an eye-opening journey, thinking about the most important people and events of my life and finding the right songs for them,” Geiger says. “I then wrote my show and worked on the music with Paul Greenwood, my pianist. In July the three of us got together for the first time.”

By fall 2006 Geiger’s musical autobiography “Making It Fit”—a title with multiple meanings—was ready for an audience. Each song, popular or obscure, had good reason for being in the lineup, which included Last One Picked, Venus, The Kid Inside, Before the Parade Passes By, and If You Love Me, Please Don’t Feed Me.

As his sold-out September debut approached, Geiger wasn’t at all nervous. In fact, he was feeling jubilant. The venue was Danny’s Starlight Room in the heart of Midtown Manhattan.

He seemed right at home in the spotlight. Armed with an easy smile, abundant charm, and a warm, pleasing voice, Geiger led his audience of friends, family, colleagues, and clients on a funny, fast-paced, and frequently poignant musical journey through his life—from awkward youth to “shamelessly romantic rascal” to present-day loving husband and doting father. Special songs were dedicated to his three biggest fans: Carin, his wife of 35 years, son Andrew, and daughter Caroline. The performance was, Geiger says, the realization of his wildest dream; he performed four more sold-out shows later in 2006.

Although he says entertaining is great fun, Geiger fully intends to keep his day job. “By the time you cover show expenses, including pianist, director, and advertising, you’re lucky to break even. Fortunately, I’m not in it for the profit. And as avocations go, it’s relatively inexpensive compared to golf or skiing.”