When Michael Feinstein swings into “Luck Be A Lady,” the opening number of The Sinatra Project tour at Benaroya Hall this week, know that you’re looking at an immensely gifted guy for whom luck has, in fact, behaved in a gracious manner.

Here’s a short version of Feinstein’s rise to recognition: The mostly self-taught singer and pianist from Columbus, Ohio moved to L.A. in 1976; frequented used record stores looking for vintage vinyl; purchased recordings that, through a contact at a piano shop, led him to songwriter/performer Oscar Levant’s widow; Levant’s widow befriended him and introduced him to Ira Gershwin’s wife; and Mr. and Mrs. Gershwin hired him as an archivist and personal assistant. Pure Gershwin, his influential 1986 debut, happened after a retired music company exec heard him playing in a piano bar.

The loose, lustrous singing on The Sinatra Project CD, released last year, is the culmination of everything Feinstein’s learned. Though his voice on the album suggests Sinatra—a gliding croon now and then holds back on a phrase or hits another with panache—Feinstein isn’t aping Ol’ Blue Eyes.

“I wanted to celebrate the totality of Sinatra’s art because he did change the way we listen to popular music by virtue of the arrangements by Nelson Riddle and Billy May and others,” he says. “But I never thought, How would Frank sing this? because he never thought about that. People have written books about how he phrased this and that or holds the seventh note for two bars or whatever. That is so absurd to me because he sang the songs differently every time.”

In concert with a 17-piece band, Feinstein will do some iconic Sinatra tunes he avoided on the album. “‘The Lady is a Tramp’ is something I wouldn’t have touched for the recording but I’ve been doing it in the shows because I realized he only sang the first chorus over and over again. And there’s a second chorus and a third chorus. So I put a thing together for live performance. It’s a great production routine. It evokes Sinatra but it’s very different from the way he did it.”

While Feinstein garners praise for the Sinatra album and concerts, he’s also just wrapped up The Power of Two—a wildly hailed, sold-out nightclub act in New York that paired him with Broadway heartthrob and former Seattleite Cheyenne Jackson (who paid his dues in musicals at the Village and 5th Avenue theaters). “He’s so extraordinarily musical,” Feinstein says. “I think that we probably will tour with it. We haven’t made any plans yet but we both would like to continue on with it.”

Before the interview ends, Feinstein confirms a random Wikipedia bio note: He and partner Terrence Flannery were married in Los Angeles. By Judge Judy. And it was her idea to get it on the books before Prop. 8 was overturned. “She’s become a very close friend of mine and Terrence’s,” he says. “We’ve spent time with her on her yacht in the south of France. She’s a very smart, very kind person—shockingly so to people who only know her from television.”

The wedding entertainment? “Liza and Barry Manilow sang.” Yeah, he knows the cliché is funny (“I mean, talk about gay,” he laughs) but he was touched by the tributes. “I didn’t tell either of them what to sing. Liza sang ‘Two for the Road’ and Barry sang a song called ‘All the Time’ that he wrote with Marty Panzer. And it was shocking to me that he picked that song because that is one that has great resonance for me.”

See? Lucky, again.