Refinement as Statement: Elling's Confident Second Act
By Flirting with Twilight, Elling had found his voice—and knew exactly what to do with it.
Flirting with Twilight arrives at a moment when Kurt Elling had already established himself as a serious jazz vocalist, but it marks the point where he stopped experimenting and started trusting his instincts completely. Following This Time It's Love, he doubles down on ballad material, building on what worked rather than chasing new ground. This is not a debut statement or a sharp departure—it's an artist at ease with himself, deepening his approach.
The album opens with Glenn Miller's "Moonlight Serenade," a pop standard that could have been precious in the wrong hands. Instead, Elling turns it into something intricate and modern, compressing it into four and a half minutes without losing its emotional weight. The Penguin Guide to Jazz recognized what he was doing here: confirming him as the finest singer of his generation. Later, Curtis Lundy's "Orange Blossoms in Summertime" becomes a vehicle for something larger—a jazz poem that honors the bassist's writing while building into genuine ambition. Elling's choices matter. He reaches for Stephen Sondheim's "Not While I'm Around" from Sweeney Todd, a song jazz singers rarely touch, and he makes it work. The New York Times critic Nate Chinen would later call him the standout male jazz vocalist of his time, and albums like this one—with their strenuously reined-in focus—showed why.
This is the record to start with if you want to understand why Elling mattered in the 2000s. It's not his most experimental work, but it didn't need to be.
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