Pop stars may come and pop stars may go, but Tony Bennett [ tickets ] has managed to outsell and outpace most of his junior counterparts, while many of them have little choice but to respectfully step out of his way, cheer him on, or secretly wish for the chance to sing in his shadow.

Since the 1980s, when Bennett started popping up on shows like Letterman, Conan, and even The Simpsons, he began establishing himself with a new generation of fans, including many up-and-coming musicians who were not at all embarrassed to be listening to the same guy who crooned for many of their parents--and maybe even their grandparents!

The 1990s only reinforced his street cred with "the kids" as he headlined a series of concerts across the nation supported by a network of alternative-rock radio stations. At the same time, he was receiving even more high profile recognition by collecting his first Grammy Awards since the early '60s.

Getting his "Steppin' Out With My Baby" into MTV rotation was followed-up with appearances on the MTV Video Music Awards, which gave way to his acclaimed "MTV Unplugged" performance in 1994, flanked by Elvis Costello and k.d. lang. The recording of that performance, incidentally, took the 1995 Album of the Year Grammy.

The 82-year-old appeared no worse for wear more than a dozen years later as he thrilled four generations of fans who turned out to Connecticut's nearly acoustically perfect Chevrolet Theater on Saturday (2/21).

Shuffling onto the stage in an understated tuxedo after a brief warm-up set from his daughter, Antonia, Bennett and his sparse-yet-stellar four-piece backing band proved they had three gears under the hood: slow, swinging, and out of sight.

Opening with "My Foolish Heart," Bennett found his groove with the ballad before a walking bass line from Jim Hughart carried the artist into "They All Laughed." One of the showpiece numbers of the entire night followed as Bennett turned to Broadway, and leaned heavily on pianist and music director Lee Musiker for the epic "Maybe This Time" from "Cabaret."

Musiker responded in kind, with an animated and breathtaking interlude, which gave Bennett a moment to relax after banging out one of his trademark high-octave vocal punches. The singer bounced back in the second movement, and proceeded to close with an even higher stretch, which he nailed perfectly, bringing most of the audience to its feet with cheers of "Bravo" echoing through the theater.

During one of the few chats he initiated between songs, Bennett pushed a familiar button by describing himself as "the very first American Idol." He went on to reveal that after taking second place in a New York amateur-singing competition to Rosemary Clooney, he was recruited by Pearl Bailey as "the only white act" on her New York review.

His presence on Bailey's showcase caught the attention of a visiting Bob Hope, who told the fledgling Anthony Dominick Benedetto he could make the kid a star if he just changed his stage name.

That night, he walked out of the theater as Tony Bennett, and never looked back.

A few songs later, Bennett and the band cranked up the energy with Gershwin's "I Got Rhythm." This number gave guitarist Gray Sargent an opportunity to shine, with a combination of complex chording and lightning-fast fills, which seemed to spur Count Basie Band alumni and drummer extraordinaire Harold Jones to pick up the tempo even more.

Sargent then stepped up to the spotlight beside Bennett, providing solo accompaniment to another one of the highlights of the evening, a sublime take on "The Way You Look Tonight."

Bennett's Chevrolet Theater set also included well-received standards like "Just In Time," "The Best Is Yet To Come" and his very first commercial hit, "Boulevard of Broken Dreams." Since he wrote the lyrics to that one himself, it was easy to see why Bennett put so much soul into its delivery, even now, nearly 60 years after he put pen to paper to produce that classic.

As he prepared to sing a mellower version of the Motown hit "For Once In My Life," Bennett revealed that he was preparing to perform the tune--reprising his Grammy-winning 2007 duet with Stevie Wonder--this week at the White House, as a guest of President Obama.

With the end of his 90-minute set in sight, Bennett wrapped the entire audience around his little finger by breaking out "The Shadow of Your Smile," "I Left My Heart (In San Francisco)" and the aforementioned "Steppin' Out." He closed with a furious "It Don't Mean a Thing If It Ain't Got That Swing," and a triumphant "How Do You Keep the Music Playing," bowing for three curtain calls before slipping out to his dressing room without an encore.

Bennett returns to the West Coast for several shows beginning March 3 in Long Beach, and heads east again for a highly anticipated stop at the New Orleans Jazz & Heritage Festival May 1.