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Doing it his way

It's a good thing Rich DiMare took a nap, because his Frank Sinatra routine requires stamina.

It's about 9 p.m. on a summer Tuesday at the swanky South End spot 28 Degrees, and DiMare isn't just singing. He's parading up and down the restaurant corridors in a suit, microphone in hand, smiling at tables of women as if he's Ol' Blue Eyes himself.DiMare is singing one of his favorites -- "Fly Me to the Moon."

"In other words .. baby, kiss me ..."

With his lively Rat Pack-style routine, DiMare has picked up three regular gigs in just a few months, making the 23-year-old the hot new lounge singer in town.Every other Tuesday night (including tonight at about 8), he's the star of Sinatra Night at 28 Degrees (1 Appleton St., 617-728-0728,, where he paces about the venue singing over a big band recording. On Wednesdays, he performs jazz, lounge, and pop classics at the Terrace Lounge in the Copley Marriott (110 Huntington Ave., 617-236-5800). On Thursdays, he sings with a pianist at Encore Lounge (275 Tremont St., 617-338-7699,, where he does standards and modern classics -- Billy Joel-style songs that the crowd can sing along to.

"28 Degrees is more of a hip lounge scene," DiMare says of his Tuesday gig, which has inspired more people to make dinner reservations that night, according to bar staffers.

Like Michael Buble and Jamie Cullum, and Harry Connick Jr. before them, DiMare is hip to the standards, despite his age. There's something about the era and the style, DiMare says. He likes wearing a suit and doing the club singer routine. When he makes it big, he plans to move up to wearing a tuxedo to "respect the audience."

"People love this music," DiMare says. "It's hard not to like these types of songs. They're so classic."

The life of a Sinatra-style singer isn't easy. First, there's DiMare's day job. Around 5:30 a.m. every weekday, he heads to KISS 108, where he is the production director for the "Matty in the Morning" show. (Sometimes hosts call him in to sing on air, and occasionally he performs modern hits -- such as 50 Cent's "In Da Club" -- in his Sinatra voice.)

DiMare sleeps in the afternoon (he calls himself a "professional napper"), living part-time with friends in the city and part-time with his family in Medford. At night, the suit comes out, and so do the hits.

Dealing with the night crawlers is also a challenge. Thursday nights at Encore Lounge attracts a mix of college students (sometimes Berklee College of Music types who have more performing experience than DiMare), hotel guests, and theatergoers. Sometimes, they've been drinking. On a Thursday night last month, a man wobbled toward DiMare until he was just about sharing the microphone and started yelling something about his son knowing Sinatra songs, too.

"Want to swing dance, baby?" DiMare said, smiling nervously.

Sometimes audience members want to play the piano or sing (a man recently came in with a bag of songbooks), and DiMare always lets them. Some patrons request challenging songs he's just learning, like "Mack the Knife," which he's found difficult to memorize.

"Fly Me to the Moon," which he recently recorded for his first demo and his website,, has become one of his staples. His favorite, though, is an old Sinatra song called "Don't Worry About Me," a self-pitying breakup number.

"I don't sing it that much," he says. "It's kind of a downer."

DiMare says he sticks to Sinatra and standards that pep up the crowd, especially when people are out for a good time.

"He's been great for us," says Bill Fortune, bar manager at 28 Degrees. "The crowd loves him. I think he has the little quirks that Frank Sinatra used to do all the time, like the snap of the finger and the point."

Three gigs a week aren't enough for DiMare, though. He has his eyes on the city's most popular Sinatra gig, Sundays at Lucky's Lounge on Congress Street, which features vocalist Adam Herbert backed by Boston jazz veteran Al Vega.

"I think I'm perfect for that room," DiMare says.

Nice work if he can get it.

Meredith Goldstein's column on going out runs every Tuesday. E-mail her at

Audio AUDIO: Hear Rich Dimare
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