Tony Bennett had many great qualities as a vocalist, but from a fan’s perspective, none meant more than his remarkable consistency. Whether he was performing in a spacious concert venue like Ravinia or a tiny club like the Gold Star Sardine Bar, he maintained the highest standards with his surpassing musicality, showmanship and deeply personal approach to popular standards.

But though Bennett, who died Friday at the age of 96, rarely departed the comforts and joys of his beloved Great American Songbook, which he promoted with the zeal of a car salesman, he always brought something new to his performances, increasingly taking greater risks as he relaxed into his later years. 

As formidable as his sense of swing and command of melody were, he wasn’t a jazz singer. But he was a master improviser, keeping expectations in the air with his shifts in tempo and key and his unparalleled ability to create instant drama with a burst of emotion or a note held almost as long as the night. 

Sustaining the word “never” (as in “never dies”) on “How Do You Keep the Music Playing,” he captured a complex world of feeling. His sudden shouts (“Time is a thief!” he yelled during a performance of “Speak Low,” in happy violation of the title) and sudden whispers left you thinking you were privy to his internal conversations. 

And then there was his magical ability (all that was missing was a rabbit jumping out of his tux pocket) to somehow make “I Left My Heart in San Francisco” sound fresh after a million renditions — convincing us that his heart was at the very least on loan to Chicago. 

Bennett’s insistence in playing by his own rules after emerging from a career rut in the 1970’s struck a deep chord among his followers, resulting in ‘80s and ‘90s masterpieces including “Bennett/Berlin” (songs by Irving Berlin) and “Steppin’ Out” (a tribute to Fred Astaire), and later appealing to pop star collaborators including k.d. lang and Lady Gaga. 

But perhaps Bennett’s most enduring quality, was his investment in happiness. No popular artist was more resolutely upbeat than this one, as reflected in his unlikely approach to Billie Holiday’s songbook. Rather than sing the pain-driven classics for which the troubled legend is best known, he revived chipper tunes she recorded including “Laughing at Life,” determined to rehabilitate her image. A daunting task, but one he approached with the dedication with which he approached everything. 

Seeing Tony Bennett perform in the late and lamented Gold Star Sardine Bar in the 1980s was like watching Renoir paint in your living room. The sense of intimacy and connection was powerful. Oh those strokes! But perhaps my most lasting image of this perennial Windy City favorite is of him at the Rosemont Theater in 1997 wordlessly intoning the melody to “I Got Lost in Her Arms” while taking a soft stroll around the piano. Here was a profound picture of contentment: A man alone, losing himself in his music even as he was helping a multitude of others find their best selves.

Lloyd Sachs is the former jazz critic for the Chicago Sun-Times.