Michael Feinstein Pays Tribute to Sinatra — Again

Michael Feinstein poses as Frank Sinatra in advance of a new album celebrating Sinatra favorites. — Photo by Gilles Toucas

Solidly Midwestern Columbus, Ohio, is a long way from the rough streets of Hoboken, N.J., where Frank Sinatra famously grew up. But that didn't stop Columbus crooner Michael Feinstein from becoming the definitive interpreter of Ol' Blue Eyes' music and the champion of his legacy.

As a sequel to his 2008 The Sinatra Project album, Feinstein's just-released The Sinatra Project, Vol. II: The Good Life is a deeper dive into the vaults, including songs that were sung by Sinatra as well as ones he never performed but were inspired by his indelible spirit.

"The first one was my attempt to pay tribute to the great man, and it's the most daunting of propositions," Feinstein says. "But the reason I was able to do it was because I did the songs differently from the way he sang them, but tried to capture his sensibility with the orchestration and taste."

The 55-year-old pianist-singer says he's comfortable with this kind of tinkering because he got to know Sinatra later in life and felt a kind of kinship with him that was rare in Frank's world. "He was marvelous to me because I was not threatening," he says. "He saw that I loved the music and because of my enthusiasm for him and his work was totally focused on the music, he loved to talk about his career and his life [with me]."

But, even with their friendship, Feinstein never dared to perform in front of his hero. "Barbara Sinatra asked me a number of times to sing but I said no because I was too scared!" Feinstein says. "I probably should have and he would have probably been great about it, but I just couldn't do it."

For the latest Sinatra Project, Feinstein tackled songs by artists who were affiliated with or motivated by Sinatra, such as Dean Martin, Peggy Lee, Rosemary Clooney, Ann-Margret and Duke Ellington, while focusing on the swinging '60s.

"One of the things I find interesting about the 1960s is that it is considered to not be a good era for music," he says. "It was good for the Beatles and an important transitional time with rock and pop bands trying to reinvent themselves. But I find the music of that time very exciting."

When it came to songs like "The Lady Is a Tramp," Feinstein switched things up by singing verses that Sinatra didn't and giving the tune more vibrant orchestration, while re-imagining another well known Sinatra track, "The Way You Look Tonight" as a kind of bossa nova by Antonio Carlos Jobim.

For almost three decades, Feinstein has been unabashed in his devotion to the Great American Songbook, which includes the best American songs of the 20th century from Broadway, musical theater and Hollywood from the early 1920s until the late 1960s. Sinatra, of course, sang the ultimate versions of many of them.

"This is just an infinite body of work that will keep me busy for the rest of my life … it's timeless, like Shakespeare or Beethoven," says Feinstein, who also finds time to oversee his eponymous foundation, which opened a Great American Songbook Archive and Museum in Carmel, Ind., this year, as well as performing steadily at his Manhattan cabaret nightclub, Feinstein's at the Regency.

Sinatra taught Feinstein that reinvention is the key to a long career, and that a musician should never rest on his laurels. "I want to release as many as albums as I can to preserve the music," said Feinstein of why he refuses to take it a bit slower after nearly three decades of work. "If I saw other people taking up the slack or continuing the work, I would probably slow down!"