Kurt Elling wrapped the audience around his finger from the moment he stepped out on stage– right after a smooth introduction by Bill Charlap, the pianist and artistic director of the 92Y Jazz in July Festival. Throughout the night, the ensemble, also including Harry Allen on tenor sax, Warren Vaché on cornet, Peter Washington on bass and Kenny Washington on drums, played through a roll of Sinatra classics.

The set kicked off with “Come Fly With Me,” setting up a very receptive crowd for a night of generation-spanning favorites, the band expressing their hope to create a ‘living room’ atmosphere, as Vaché had wanted ‘zero rehearsals’ for the set! Songs included “Witchcraft,” “Luck Be A Lady,” “Moonlight In Vermont,” “April In Paris” and the show-stopping finale “You Make Me Feel So Young.”

Vaché warmed up after a few numbers and shimmered through in his “Day In Day Out” solo, mesmerizing the audience. Allen played a consistent effort and bounced off of Vaché and Peter Washington in both “April In Paris” and “Nice ’N’ Easy,” with Washington’s intense bass playing reaching eye-opening heights. As implied by Vaché, Washington would be rich if he was paid for every performed note, due to the immense speed and amazing rhythms performed.

Bill Charlap, leading the ensemble, stole the show with his piano rendition of “Only The Lonely.” The intensity of his performance and delicate playing felt like the sound of his heartstrings vibrating, with each note sounding like a teardrop, echoed by the multitude of hearing aids going-off in the concert hall. The stillness reverberating afterwards brought tears to my eyes and everybody else’s.

The star of the night, however, was undeniably Kurt Elling. He was “Too Marvelous For Words;” his carefree and cool attitude brought Sinatra back to life with a modern edge. He entertained the crowd with “How About You,” singing, “Caitlyn Jenner’s looks gives me a thrill, how about you?,” sending the aged crowd into an uproar of laughter. Kurt’s standout performance was “In The Wee Small Hours of The Morning,” where I feel his expression exceeds that of Sinatra’s, embodying a heartbroken romantic in an age of cynicism.

The night played out as if the audience was listening in to a jam-session of sweet-talking and musings between the players, with simplicity and sensitivity. What great talents brought together, and what a night to remember.

-Jason Kwan