Singer Kurt Elling admits there are risks to doing tributes to great artists, but says it is "part and parcel" of being a jazz performer.
But he says paying homage to Frank Sinatra has its own special demands.
"Sinatra has his own cache," he says about the shows he will do Saturday at the Manchester Craftsmen's Guild on the North side. "But I think there will be people who will be happy to see me do some songs as he did them and those who will be happy to see me taking the music a different way."
The Grammy award-winning Elling, 44, one of the leading singers in jazz, is a master of vocalese who can give lyrics to a famous solo by Freddie Hubbard or Dexter Gordon. But he also pays tribute to some of the classics songs and their performers, as in "Dedicated to You," an album that was a tribute to the famous 1961 album, "John Coltrane and Johnny Hartman."
But he says the Sinatra show is its own challenge because of the great popularity of the singer. He has only done the show three times and says this one could easily be the last because "I don't want to hit up the old man for a cheap dollar."
But he says he liked the idea of doing some of the famous hits of Sinatra, particularly those that were popular in a concert tour this show commemorates.
It was 50 years ago -- "practically to the month," Elling says -- that Sinatra went on tour with the Bill Miller Sextet, reducing his big band sound to a small group format.
This show will do the same thing, featuring a quintet led by Elling's piano compatriot, Laurence Hobgood. It also will include one of the hardest workers in jazz accompaniment, saxophonist Joel Frahm.
Elling is one of those performers who always is looking for projects to give life to his work. Rather than simply recording a group of songs, he tries to find themes for presenting them, as in his Coltrane-Hartman collection or in "This Time It's Love," a wide-ranging look at romance.
His next album, which he is just beginning to work on, will consist of works from the Brill Building, the New York office building that was the home for songwriters from Tin Pan Alley days through Carole King.
He says the "great body" of music that came out of that building will help create an broadly varied album.
"I like to challenge myself with new ideas," he says.