Standard Bearer: Your Guide to Tony Bennett

stand·ard-bear·er — a leading figure in a cause or movement; one that leads an organization; the leader or public representative of a group of people who have the same aims or interests.

It is becoming increasingly difficult for an artist, singer or band to be sui generis or truly unique. More and more you discover that the things you may find fascinating today have their roots in things of the past and that it often holds true that there is nothing new under the sun. But it has sometimes been refreshing for me, those few times I’ve stumbled on either an album that started a genre or the first film to use that technique. Even more so when I discover an artist in a certain medium who truly has no peer; one to whom no one else can accurately compare. It’s exceedingly rare when you find someone who truly does stand alone.

“I never went for a hit record; I always wanted a hit catalog.”

– Tony Bennett

Tony Bennett may not be the greatest singer of the Great American Songbook that ever existed. There may be things in his career that you find objectionable or hard to defend. But it would be hard to deny that his career has been singular; no one has cut a swath exactly like the one Bennett has. Not to minimize his achievements but the most compelling aspect of his life’s work has been its longevity, its sustainability. His appeal certainly has been unique through the years but it is the “through the years” part that always strikes me. The work of Tony Bennett was noteworthy in 1950 and he was a significant enough personality that his battle with Alzheimer’s Disease received much press in early 2021, over 70 years later.

Along the way, Bennett has been an outspoken advocate for American Popular Standards or the Great American Songbook, the canon of jazz standards and popular songs created by songwriters in the US in the early days of the 20th century. In a business that finds even the most polished and accomplished singers stooping to record songs of lesser quality in the hopes of scoring a hit – ditties designed to catch the fancy of the day – it is indeed rare to find a vocalist who has seldom compromised, one who has maintained a catalogue of timeless music that never has to be put into context or explained. Tony Bennett is such a vocalist.

I have written two other “guides” in the past here at SoulRide, one on Nat Cole and one – actually, four parts – on Frank Sinatra. The purpose of these articles is not so much to profile the life of the artist but to pinpoint what the artist was releasing and when. These articles should help people who want to purchase an artist’s albums but don’t know what they want or like from that singer. In Bennett’s case, some folks may know that he recorded “I Left My Heart in San Francisco” but they don’t know when or what else he was doing at the time or what they can purchase to get that song and others like it. Well, that’s what you’ve got me for. Let’s break down the storied recording career of Tony Bennett, pinpoint his best recordings and the albums – as opposed to contemporary compilations – that you should seek out.


With a few breaks, Bennett has been signed to Columbia Records since 1950, OK? That’s over 70 years. Ridiculous. Mitch Miller brought Tony on board and warned him not to try to imitate Frank Sinatra, who had recently left the label. Bennett started out with a series of light pop songs and he had much success on the charts. Consider that between 1951 and 1954, 20 of Tony’s singles reached the top 30 of the pop charts. Included in these early tunes is his first hit, “Because of You”. Number One in the US and in Australia, the wonderful record is where Tony Bennett’s discography effectively starts. Add to this other Number Ones like his cover of Hank Williams’ “Cold, Cold Heart” and the majestic “Rags to Riches” and other hits such as “Blue Velvet” and “Stranger in Paradise”.

It took until 1957 for Mitch Miller to get up to his antics. Convinced that goofy pop ditties were the only way to go (see “Mama Will Bark”), Mitch brought “In the Middle of an Island” to Bennett to record and Tony bristled violently. Setting a precedent for the next 70 years, Bennett had his worst-ever disagreement with Miller and grumpily ran through the lyrics once listlessly. Miller begged him to record it, to sing it just once and Tony did just that. The one-take ditty went to #9 on the charts, giving Bennett his biggest hit in three years. Thing is, “In the Middle of an Island” – also recorded by Tennessee Ernie Ford – is a delightful tune and actually played a prominent role in a novella I wrote when I was young, one that gave me my only rejection so far. One submission to date, one rejection. But Tony Bennett knew what he wanted.

Tony had, in the past, brokered deals to record music he loved at the cost to him of cutting some hit singles he may have thought little of. His first 12″ LP, Cloud 7, was released in 1955. A departure from his chart hits, Cloud 7 was a straight-up jazz record featuring a small combo of jazz musicians. I have a real soft spot for this album. The first of the three times I’ve seen Tony Bennett live was October 14, 2004 at Toronto’s Roy Thompson Hall. At the time, this venerable old concert hall had it’s own music store and, before the show, my wife and I browsed the shelves which had been stocked with Bennett’s CD’s. One of the ones I bought that day was Cloud 7. The show was excellent and I listened to a lot of Tony that autumn and every autumn since then.

As Tony entered the Sixties, he had scores of singles and ten albums in his catalogue and Mitch Miller had been recording him much the same way Sinatra was being recorded over at Capitol Records. Bennett was cutting singles for jukeboxes but his long-players were serious affairs stocked with standards. Case in point is Tony’s first album of the decade, To My Wonderful One, featuring songs like “September Song”, “Autumn Leaves”, “Laura” and “April in Paris”. And the following Tony Sings for Two contained five songs by Rodgers and Hart and featured only Tony’s voice and Ralph Sharon’s piano, a format Bennett would return to later and would still be utilizing in 2015. Then in 1962, Tony Bennett wrote his name in the history books. “I Left My Heart in San Francisco” was brought to Tony by Ralph Sharon after the tune had languished unrecorded for nine years. The song became Tony’s biggest chart hit – since “In the Middle of an Island”! – and went on to win two Grammys. While it would later become iconic, the immediate change came in the fact that the I Left My Heart in San Francisco album was his first album to chart after his previous 10 dating back to 1957 had failed to do so. This seemed to have cemented in everyone’s mind that Tony’s status was now that of an album artist. The I Left My Heart in San Francisco LP contained classy songs like “Once Upon a Time”, “Tender is the Night”, “The Best is Yet to Come” and a personal favourite, “Have I Told You Lately?”. Tony would release virtually no non-album singles going forward and the San Francisco album set the template for LPs to come.

During the remainder of the 1960’s, Tony Bennett became Tony Bennett, recording albums with a sound that became inextricably linked to what we all think of when we hear his name or voice. He recorded what I call contemporary classics, what is effectively the second phase of Great American Songbook tunes. His very next album was another hit. I Wanna Be Around… gave the world classic Tony tunes like the title track and “The Good Life” and also gems like “Once Upon a Summertime” and “Quiet Nights of Quiet Stars (Corcovado)” delivered in a rich orchestral setting. Followed then were quality albums with songs from the Songbook and also from Broadway shows. When looking at the track listings, you marvel at how Tony and his team were somehow able to find songs from quality sources, never once looking to the current hit parade. Also notable is that, aside from 1966’s The Movie Song Album, there are no concept records.

If I Ruled the World: Songs for the Jet Set was a 1965 album that featured another two songs from Antônio Carlos Jobim and the majestic title track. “If I Ruled the World” came from the musical Pickwick and supports scholar Will Friedwald’s thesis that Bennett has patterned much of his approach to a song after Frank Sinatra’s 1958 recording of “Where or When”. The song starts off quietly and gently and builds to a thundering crescendo. Whether Tony did this consciously or not, much of his grander recordings from this era employ this technique – which, it could be argued, is the only technique to be employed with such songs anyway.

By the summer of ’69, Tony Bennett had achieved the remarkable; he had remained relevant through the rock/hippie era, never compromising and managing to find standards and songs from Broadway and reputable songwriters to fill his albums. His 1969 album I’ve Gotta Be Me finds him recording the title track from Broadway that had been a hit for Sammy Davis, Jr. and is – despite it’s source – close to what you might consider a “hit of the day”. The record also features “Alfie”, “What the World Needs Now is Love” and “(Theme from) Valley of the Dolls”, all recent hits (of course, it does also contain the chestnut “They All Laughed”). This leads up to most infamous album in Tony’s catalogue.

There are many sides to many debates. I try not to paint anyone in history with the “broad brush stroke” whenever possible. So, there is a caveat when I say that record mogul Clive Davis may be high on the list of “Rock & Roll Villains” with Col. Tom Parker and Mike Love. It is true though that Davis, like Mitch Miller before him, felt he had his finger firmly on the pulse of contemporary music and the tastes of the record-buying public. He was the head of Columbia Records in late ’69 when he decided that Tony needed to revitalize his career by recording a full “hits of the day” album. By this point, many pop singers of standards had made such attempts in the hopes of maintaining chart presence. Bennett was vehemently against it from the start, so much so that he actually vomited before the first recording session. The resulting Tony Sings the Great Hits of Today! was a “disaster” and did not make Davis or Bennett happy. When Columbia again pressured Tony to follow this up with a similar record – Tony Bennett’s “Something” – Bennett had had enough and left the label.

Like too many singers of his ilk, Tony Bennett entered a wilderness in the 1970’s. He moved to England, started his own record label and struggled with cocaine addiction. Some light can be found in this period, though, in the form of Tony’s two records with pianist Bill Evans. At his nadir, Bennett was being hounded by the IRS and was courting death with his addiction. He reached out to his grown sons for help and music’s greatest “victory lap” was about to begin.

It began with his return to Columbia – this time with creative control – and his resurgence perhaps can be said to have began on September 15, 1992 with the release of Perfectly Frank. Setting a precedent for the rest of his recording life, Bennett released this record with a unifying theme. A tribute to Frank Sinatra, it had him essaying tunes Frank had put his stamp on like “I’ve Got the World on a String”, “The Lady is a Tramp” and “Angel Eyes”. Significantly, the songs were presented in a small group setting and this sets this record and subsequent ones apart from the later work of Sinatra. As opposed to a huge orchestra – though Bennett would later employ such outfits – Tony opted often for piano, bass and drums and just stood there and sang. This seemed to resonate with people as it was clear Tony was not hiding, he was simply presenting the songs he had always loved with his rich and resonant mature voice.

His visibility increased and younger listeners took notice. His sons made the savvy move of avoiding Vegas-type clubs and instead booked Tony on late-night talk shows and when he appeared on the MTV Music Video Awards alongside the Red Hot Chili Peppers the comeback was complete. Tony – uncompromisingly clothed in stylish silk suits – gained a rep as a survivor, a dude and a great artist. The video for the title track of Steppin’ Out (1993) went into heavy rotation on MTV and Music Television also obliged by having Tony featured in one of the network’s Unplugged concert settings. Bennett’s MTV Unplugged album won that year’s Grammy for Album of the Year, quite an achievement for a 68-year-old vocalist.

The charts and the Grammys once again took notice of Tony Bennett and, starting with Perfectly Frank, Tony would routinely place records high on the jazz charts. Consider that Bennett would go on to release some niche albums (Christmas records and one of children’s songs) but apart from these, every single release of Tony’s would either reach #1 or #2 on the jazz charts; 11 at Number One, 3 in the runner-up spot. If the record charted at all, it went to the upper reaches. Between ’06 and 2018, every one of Bennett’s 7 records have topped the jazz charts. Now for the bad news.

Since 1992, all of Tony’s releases have had a theme or a concept. The songs of Ellington, the songs of Fred Astaire, songs made popular by females….. While this may be viewed as tiresome, one could argue that the unifying theme doesn’t matter as long as the performance is good. Additionally, an album of songs by Billie Holiday is much preferred to the dreaded “duet” album. We have Frank’s people to blame for this phenomenon. The staggering success of Frank Sinatra’s two duets albums of the mid-1990’s lead to a plethora of releases in the same vein by a variety of artists. Starting in 2001, all of Bennett’s releases have featured another prominent artist; or lots of them. Tony’s 2001 duets album Playin’ With My Friends: Bennett Sings the Blues was his highest-charting album on the pop charts since The Movie Song Album in 1966 – 35 years previous. This lead to an even higher-charting record of Louis Armstrong songs sung with Canadian k.d. lang.

Then came the biggest-selling album of Tony Bennett’s career, Duets: An American Classic (2006). While a much better record than either of Sinatra’s duet offerings, there is still what I consider a major problem with this record. Here, Bennett sings with appropriate partners like Barbara Streisand and Michael Bublé. But he also inexplicably mixes it up with the Dixie Chicks, Tim McGraw and George Michael. There is something inherently wrong with records like this, records like Robbie Williams’ albums of standards or Rod Stewart’s carnage of the Songbook and it is this – who are these records for?

If you are an ardent Tony Bennett fan, do you need to buy a CD on which Tony sings “Rags to Riches” with Elton John? Conversely, if you’re heavy into Paul McCartney, how much do you care about him joining Bennett for “The Very Thought of You”? Seems to me these records don’t appeal to anyone’s fans, but it seems they appeal to everyone in general. Tony followed this up with the aptly named Duets II (2011) – John Mayer? Queen Latifah? – and the following year’s Viva Duets, an album of songs sung in English, Spanish and Portuguese with Latin American singers. Again; who’s to care about these releases? One record from this period stands out and I can highly recommend it. The Art of Romance from 2004 is one of the few from this period that did not chart on the jazz charts (#65 Pop) but it is simply a gorgeous album of singing with small group and light strings. There is nary a gimmick to attract attention to this record. The songs are unknown, rare even, and they are songs that Tony had never recorded before. He also debuted as a songwriter, writing lyrics to Django Reinhardt’s “Nuages” and christening it “All for You”. It’s a fine record and, really, perhaps the most unique in his catalogue.

The Art of Romance won the Grammy that year for Best Traditional Pop Vocal Album – or the Tony Bennett Award. I’ve always considered that this Grammy was invented as a way to honour Bennett for his extraordinary albums from this era. Actually, the first recipient was Natalie Cole for her album featuring a duet with her late father. But – much to Michael Bublé’s chagrin – Bennett has owned this award. It’s not a Tony Award but it might as well be the Tony Grammy. Tony’s 14 non-Christmas records between Perfectly Frank and his album with pianist Bill Charlap The Silver Lining: The Songs of Jerome Kern (2015) have been awarded the Tony Grammy 13 times; Viva Duets was nominated but lost to Bublé’s To Be Loved in 2014.

Tony awards.

The only single vocalists that Bennett has recorded duets records with have been females, two of them – k.d. lang and Diana Krall – Canadian and the other is Lady Gaga, a singer with whom Tony has recorded two albums, with a third coming in 2021. No fool Bennett, he has kept good company as both lang and Lady have stunning voices while Krall is a consummate jazzbo pianist and great singer.

Are Tony Bennett’s records of the last 30 years worth owning? Yes. Are they going to make you forget his glory years? No. The albums of this era are great if unremarkable but it is remarkable that they exist at all. They don’t give a reviewer much to report on. There are perhaps not many individual highlights to pinpoint but they have an extremely high level of class and quality that – when added to the knowledge and wisdom that latter-day Bennett brings to these timeless songs – fills your ears and your spirit with a good feeling. A feeling of gratitude, even. The pleasure that comes from hearing a legend, a vocalist that has spanned eras and decades without ever losing his way – or by not losing his way as much as others did.

The premise of this article may be that Tony Bennett champions the Great American Songbook. Yet when you look at the following list of Bennett’s greatest recordings none of them are really from the Songbook. Thing is many of these have become classics due to Tony’s having sung them.


10. “Have I Told You Lately?” (1962) — From I Left My Heart in San Francisco and from the musical I Can Get it for You Wholesale, written by Harold Rome // A gentle recording with pleasant lyrics, Tony’s rendering of this tune is particularly pleasant for those men enjoying a wonderful marriage. I sometimes even get emotional. “When I think of all the girls I could have been stuck with I sure was in luck with the one I drew. Have I told you lately how much your husband loves you?”

9. “When Joanna Loved Me” (1964) — From The Many Moods of Tony, written by Jack Segal (“When Sunny Gets Blue”) and Robert Wells (“The Christmas Song”), who was born Levinson but thought the name “Wells” was so cool that he chose it // Only typically brilliant from Bennett. Typically wonderful piano tinkling and smooth brush work on the snare. Sweepingly sad strings lamenting the loss of love. Just a perfect example of warm singing from one of the warmest voices.

8. “I Wanna Be Around” (1963) — From I Wanna Be Around…, written by Sadie Vimmerstedt and Johnny Mercer. Sadie was a grandmother in Youngstown, Ohio who sent Mercer this song idea and the first line in 1957. She was inspired by Frank Sinatra being left by Ava Gardner after Frank had left his wife for Ava // More great piano; Tony knew from pianists and worked with two of the best throughout his career. Ralph Sharon (1923 – 2015) tickles the ivories here and the tune takes a gentle, mid-tempo lope through your frontal lobe, providing soft feelings and a mellow glow.

7. “The Boulevard of Broken Dreams” (1950) — Single released in 1950 as Tony’s major label debut; he was signed by Columbia on the strength of the demo of this song, written by Al Dubin and Harry Warren in 1933 // Vigorous arrangement with a pulsating rhythm featuring percussive castanets. Tony’s vibrant tango take on this tune showcases his virility. He bosses his way through it, ending up with a full-throated finale. Always a joy to hear.

6. “Once Upon a Summertime” (1963) — From I Wanna Be Around…, a French song written by Michel Legrand, Eddie Barclay and Eddy Marnay with English lyrics by Johnny Mercer // “Once upon a summertime, if you recall…” From the start, it’s about memory, remembrance. The melancholy strings set the tone. “A bunch of bright forget-me-nots was all you’d let me buy you”. Tony’s gentle voice continues Mercer’s sad tale. This sounds like the fleeting nature of memory, the warmth of a summer complimented by the warmth shared by two who are no more. “Now, another wintertime has come and gone, the pigeons feeding in the square have flown but I remember when the vespers chimed. You loved me once upon a summertime”. A beautiful voice sharing a beautiful reminiscence, one we can all relate to.

5. “Yesterday I Heard the Rain” (1968) — Title track from Tony’s 1968 LP, a song called “Esta Tarde Vi Llover” by Mexican Armando Manzanero Canché (1934 – 2020), English lyrics by Canada’s Gene Lees, prolific lyricist who wrote English words for many songs of Antônio Carlos Jobim // A great example of what Bennett did best at this time. Grandiloquent and emotional, this is another sad tale in which even the elements lament the loss from Tony’s life. She is all around him and he hears her name everywhere. She is not to be forgotten. “Yesterday I saw a city full of shadows, without pity. And I heard the steady rain whispering your name…” Sublime.

4. “Rags to Riches” (1953) — Single released in 1953 with Canadian Percy Faith’s orchestra, written by the Broadway team of Richard Adler and Jerry Ross. Based on a Russian tune, Tony’s version topped the charts for eight weeks // Hard to hear the bold opening strains of this classic without picturing Martin Scorsese’s Goodfellas. The visuals of this film certainly help take you back to the early Fifties and when you hear Tony on this one you realize it’s a wonderful time capsule. Elvis Presley loved the grandeur of this song and recorded it in 1970.

3. “I Left My Heart in San Francisco” (1962) — Noted title track and Tony’s signature. Only significant composition of George C. Cory, Jr. and Douglass Cross // Written for Claramae Turner who was the first to sing it but never recorded it. After Tennessee Ernie Ford turned it down, it languished until Bennett’s pianist Ralph Sharon brought it to the singer. Tony debuted it to much acclaim in the Venetian Room of the Fairmont Hotel in San Francisco. He recorded it a month later in January of ’62 and it was released as a single in February. And the rest, as they say….

2. “Maybe This Time” (1995) — From Here’s to the Ladies, written by the venerable duo of John Kander and Fred Ebb, successful stage musical songwriting team // A song of “desperate hope”, it was made popular when sung by Liza Minnelli in Cabaret (1972). Tony included this on his album of ’95 that paid tribute to women of song and featured the signature tunes of many chanteuse’s of the past. Yet again, a quiet piano opening leads to Tony’s mature voice and brushes on the snare. The desperate hope is apparent early; “maybe this time she’ll stay…” Tony’s pure tones begin to rise until he delivers a grand finale. Often performed live during this time, the song lends itself nicely to Bennett’s flair for the big finish. The absence of orchestra gives it an intimate feel and he ends so confidently that the listener has no doubt that a victory is on its way.

#1 “Fly Me to the Moon” (1965) — From If I Ruled the World: Songs for the Jet Set and written in 1954 by Bart Howard for Kaye Ballard, for whom the preceding tune was also penned // Allow me to get personal on this one. Early in my exploration of this type of music, I heard Frank Sinatra’s trademark version of this tune from his album with Bill Basie and Quincy Jones. I was bowled over by the coolness of Frank’s take and could tell right away that it was recordings like this that gave Sinatra his rep as the greatest swinger who ever lived. I then heard Bennett’s rather placid version and immediately was disappointed, thinking Bennett had missed an opportunity. Bennett also includes the verse that opens the lyric, something I’d never really listened to and that Frank omits. Sounded like a totally different tune to me, indistinguishable from any other ballad. Then I saw Bennett at Roy Thompson Hall as I mentioned earlier. During the show, he raved about the incredible acoustics of the building. The Hall had suffered from poor sound for years and extensive renovations – $20 million worth – were finished two years before Bennett’s show there. Among other improvements, spaces in the ceiling that had allowed sound to leak into the attic had been closed. To illustrate the improvement, Bennett asked us to listen to him sing this next song without a microphone (the Hall seats 2500). He began the tune – “Poets often use many words…” – and I did not recognize it and didn’t know what was coming. I will never forget, as long as I may live, the sound that resonated through the place when Bennett’s bell-like voice went into the tune proper; “Flyyyyy me to the moon…”. What can I say? I had never heard anything like it, I haven’t since, nor do I expect to. It was absolutely spellbinding. Pure sound. Pure tone. Pure class. Pure Tony Bennett.

You’re good, Mr. Bennett. You’ve done enough. Thanks.

Leave a Reply

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out /  Change )

Google photo

You are commenting using your Google account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s