Live review: Kurt Elling brings swing, sensitivity and Sinatra to the 2015 Portland Jazz Festival

Kurt Elling was talking about the Grammys.
Not this year's, with Beck and Beyonce and Kanye West's big mouth. But the first one, in 1959, where Frank Sinatra competed against himself for Album of the Year, and was up for Song and Record of the Year with “Witchcraft,” with Nelson Riddle's charts for the song nominated for Best Arrangement.

“Times have changed,” Elling said, with dry regret.

On Friday, Elling, perhaps the most well-regarded male jazz singer of his generation, turned back the clock at the Portland Jazz Festival: to the mid-'60s, when Sinatra was engaged in an energizing collaboration with Count Basie and his orchestra and arrangers including Riddle and Quincy Jones. “Watch out!” he bantered as he took the Newmark Theatre stage, taking on the role of Sinatra as commanding entertainer and Rat Pack leader as well as unmatched vocalist.

Elling's show was in part a history lesson in the year of what would've been Sinatra's 100th birthday — between each song, he'd share trivia, such as those Grammy statistics or Riddle's race to finish the arrangement for “I've Got You Under My Skin,” which, the story goes, he wrapped up in the back of the family station wagon as his wife drove him to Capitol Studios. In lieu of Basie's band, Elling had the Art Abrams Swing Machine Big Band, who did justice to Riddle's legendary shout choruses and shifted quickly to each new chart as Elling counted off another song.

But it was a showcase for Elling as well: he did a pair of new arrangements of Sinatra classics, including a reimagined “Come Fly With Me” with only a hint of the original's melody. Elling's version was showier, but the reworked music also captured the hopeful, nervous quality of the song's persuasive message, rather than the slick confidence of a vacation under way that Sinatra's conjured. For two songs, the band quieted and Elling was joined by Bill Charlap at the piano, which drew out Elling's most tender vocals — particularly on “In The Wee Small Hours of the Morning,” to which Charlap added a patient solo that took a long pause before sprinkling in the familiar melody. Charlap didn't play many notes, but they all had something to say.