Happy 96th birthday to Anthony Dominick Benedetto. It’s a gift that he’s still here, even if (after his triumphant farewell performance at Radio City Music Hall last year) he’s no longer performing due to his struggles with Alzheimer’s.  Tony’s long, winding career was as unique as his artistry was commanding. I came to his music primarily through the jazz lens (and had the privilege of hearing him with his trio in an intimate setting in the early ‘90s, shortly before he “blew up”) and even if one looks only at that (and obviously it’s just one facet), there’s so much in there. Some debate whether Tony should be classified as a jazz singer (a can of worms I sometimes allow to be opened when I’m teaching) but if we address the question through the lens of his mastery of the craft, the two part answer is clearly 1) yes, and 2) he’s a giant, so who the heck cares? Here is a small sampling of some of my own favorites over a 60+ year span.

1 ) “Cold, Cold Heart” from Because of You (1951)

While lushly orchestrated crooning is not my personal favorite side of Tony’s artistry, I needed to include at least one such example, in this case the early-career single that helped bring the music of Hank Williams to a broader audience. It’s almost disarming how smooth his voice is here in his mid-20s.

2 ) “Just One of Those Things” from The Beat of My Heart (1957)

Most of this song is a duet with Art Blakey on drums (notably not the only such track from this year – dig his duet with Chico Hamilton on “Crazy Rhythm” too) and it cooks while Tony somehow keeps his cool.

3 ) “Jeepers Creepers” from Strike Up the Band (1959)

I always thought this song was kind of cheesy (probably because I was introduced to it on the Muppet Show), at least until I heard Tony swinging with the Count Basie Orchestra on this version.

4 ) “One More for My Baby (And One More for the Road)” from Bennett & Brubeck: the White House Sessions (1962, released 2013)

I had to include some version of this signature Tony number, and once this lighthearted, grooving live version entered the scene it became not only my favorite duet version of the tune (sorry John Mayer) but quite possibly my favorite overall.

5 ) “Out of This World” from Jazz (compilation) (recorded 1964)

This is one of the most intense modern jazz contexts of Tony’s discography (which is saying something) – the session is one of the few times Herbie Hancock and Elvin Jones recorded together and Ron Carter and featured soloist Stan Getz are no slouches either. Tony, of course, sounds nonplussed by all this.

6 ) “When In Rome” from The Bill Evans/Tony Bennett Album (1977)

This entire album is one of my absolute favorites in all of recorded music, so if I waited 10 minutes to publish it I’d probably change which of these songs I included three more times. But the playful phrasing and delightful interplay on this one make it my most frequent go-to as a smile-inducer.

7 ) “Cheek to Cheek” from Bennett/Berlin (1987)

This record comes from the beginning years of Tony’s commercial comeback (if, in a career this long, that characterization is even valid) and it’s full of fun guest appearances from jazz giants including Dizzy Gillespie and Dexter Gordon. This one features the great George Benson and is also a fine example of Tony’s assurance on up-tempo songs.

8 ) “All Of You” from MTV Unplugged: Tony Bennett (1994)

Perhaps the culmination of the aforementioned comeback is this bewildering yet wonderful step into the pop culture mainstream, one that came without an iota of artistic compromise. This is one of my favorite songs to hear Tony sing, and I particularly love hearing him shout out longtime pianist Ralph Sharon in such a highly visible setting.

9 ) “Body and Soul” (with Amy Winehouse) from Duets II (2011)

One really lovely thing about Tony is the way he nurtured and amplified the talents of younger artists who on paper were not stylistically coming from the same place he was, from K.D. Lang to Lady Gaga. His fondness for Amy Winehouse is a great example of this, and hearing them both on the most frequently performed of jazz ballads shines a light on this vision, not to mention his masterful phrasing.

10 ) “I’m Old Fashioned” from The Silver Lining – the Songs of Jerome Kern with Bill Charlap (2015)

Nearly 90 at the time of this recording, Tony could have been forgiven if he’d lost a few MPH off his fastball, and yet somehow his command was undiminished. While Tony’s own group has long provided sympathetic and grooving accompaniment, Bill Charlap’s trio is also a perfect fit here.

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