Written By Sherwood Kohn

Three years ago, Steve Flynn quit his well-paying job as a senior district manager in the marketing department of the Aon insurance corporation and started singing like Frank Sinatra, Dean Martin and Bobby Darrin.

Well, not quite. It wasn’t that miraculous. He did give up a well-paying job at Aon and took a two-thirds cut in income to pursue his love of singing. But like many “overnight sensations” in show business, the 43-year-old Mt. Airy resident had been singing that way in small clubs, at weddings and anywhere else he could wangle a gig, for more than 10 years while he worked in sales.

Born and raised in Glendale Heights, Illinois, a suburb of Chicago, he started singing and playing guitar at an early age. After graduating from high school, he hooked up with a small band, in which he played guitar.
One night, the band’s singer fell ill and Steve stepped in. He found that his vocal range was almost identical with Sinatra’s. A career was born.

Last year, Steve, whose eyes, like Sinatra’s, are blue and whose hair is thinning (also like Sinatra in his 40s -“So be careful what you wish for”), did 245 shows -18 more than he did in 2005 – some 60 percent of which are “senior related.”

That means that Steve sang to about 147 gatherings of elderly people in nursing homes, senior centers and similar establishments last year. The remainder of his performances were weddings, parties, corporate events and engagements arranged for him by his agent and events planners (He has even sung “My Way” at a funeral.)

We caught up with him one Saturday at the Future Care–Cherrywood nursing home in Reisterstown, where he was entertaining some 25 elderly people in wheelchairs.

In mid-afternoon, the 6-foot singer was dressed in a tuxedo, complete with black tie, patent leather shoes, and a red pocket handkerchief. His hair was slicked down and he had set up his own sound system, which provided him with fully orchestrated, big band musical arrangements, many of them by Big Band Era star Nelson Riddle.

“I love this music,” he said. “I truly love the standards. The songs from that period told stories. The music won’t go away. It’s still relevant.”

After a few minutes of patter, Steve launched into his repertoire, which included several Sinatra arrangements, a Perry Como version of “Silver Bells,” a rousing rendition of “Chicago” (“my home town”), and a big finish: “New York, New York,” many of which were punctuated with “Hup! Hup!” encouragements and blandishments directed to the women in his audience. They ate it up.

Steve is, he said, probably one of the top entertainers for the area’s senior communities, a distinction that might discourage a lesser performer.

“It’s not depressing,” he said. “It’s enriching. I am truly blessed to be doing what I love. If I see just one or two people in a crowd grinning from ear to ear, that’s satisfying.”-S.D.K.