Top 10 Tony Bennett Albums

Tony Bennett Albums

Photo: Featureflash Photo Agency /

He has been a household name since the 1950s, and his recent reluctant retirement due to the onset of Alzheimer’s was covered on 60 Minutes. Tony Bennett has always stood for musical integrity, refusing to get swayed into performing commercial and lightweight material in order to gain more sales. A popular attraction for 70 years, his loyalty to the Great American Songbook has been consistent ever since its heyday.

He was born Anthony Dominick Benedetto on Aug. 3, 1926 in Queens, New York. He grew up in poverty but had a love for music from an early age and sang for the first time in public when he was ten, beginning an 85-year career. At 13, he began performing as a singing waiter in several Italian restaurants. Young Benedetto dropped out of school at 16 to support his family, working odd jobs and singing wherever he could. Drafted into the Army, he fought in Europe during the last part of World War II. After the war ended, he sang a bit overseas before being discharged in 1946.

The singer freelanced in New York and in 1949 made his first recordings. Discovered by Pearl Bailey, he opened for her at a prestigious club. Bob Hope caught the performance and took him on the road, shortening his name to Tony Bennett. He made a demo recording of “Boulevard Of Broken Dreams” in 1950 which led to him being signed to the Columbia label, The following year he had a big hit with “Because Of You” and Tony Bennett was on his way.

#1 – Fifty Years – The Artistry Of Tony Bennett (Columbia/Legacy, 1950-2001)

There have been many samplers and retrospectives of Tony Bennett’s career, but this five-CD set is very difficult to beat. Beginning with “Boulevard Of Broken Dreams,” and ending in 2002 with “What A Wonderful World,” the 110 selections include all of Tony Bennett hits with one CD covering the 1950s, two consisting of recordings from 1960-67, disc four zooming through 1967-89, and the final CD doing a particularly good job of summing up the 1990s. The booklet covers his life and career well, making the box (released in 2004 and still findable) the perfect place to begin in exploring Tony Bennett’s music.

#2 Cloud 7 (Columbia, 1955)

Tony Bennett was a regular on the pop charts in the 1950s. “Because Of You,” ”Cold Cold Heart” and “Rags To Riches” were #1 hits, “Blue Velvet,” and “Stranger In Paradise” were very popular, he filled nightclubs, and Bennett not only appeared on television but hosted some short-term series.

Despite that, it is fair to say that he did not let success go to his head. In fact, Tony Bennett showed from the start that the quality of the songs he performed was very important to him, and he turned down many requests to record novelties. His true love was jazz.

It has long been debated whether Tony Bennett can be considered a jazz singer. Certainly he utilized jazz artists throughout his career and he always swung (as did Frank Sinatra). There are times when he seemed to cross over but, because he rarely ever improvised, instead sticking to set routines and melody statements much of the time, Tony Bennett can be thought of as a superior middle-of-the-road pop singer who was influenced by swinging jazz.

No matter, Tony Bennett did record some albums of strong interest for the jazz audience. After his pop successes for Columbia, he was able to talk the label into letting him record Cloud 7. For the first time he was heard at length with a combo rather than a large orchestra. The set of jazz standards has the singer joined by a septet with guitarist Chuck Wayne and altoist Dave Shildkraut, putting tender feeling into “I Fall In Love Too Easily” and swinging away on “Give Me The Simple Life.”

#3 – Tony Bennett Jazz (Columbia, 1954-67)

Whenever he could, Tony Bennett recorded with jazz musicians. He admired their musicianship and ability to react immediately to his singing. This fine collection (originally a two-Lp set that became a single CD) has Tony Bennett interacting with such musicians as pianist Herbie Hancock, drummers Art Blakey and Elvin Jones, flutist Herbie Mann, tenor-saxophonists Stan Getz and Al Cohn, cornetist Nat Adderley, the Count Basie Orchestra, and his long-time pianist Ralph Sharon among others. The singer always sounded joyous in these types of settings.

#4 – The Beat Of My Heart (Columbia, 1957)

This unusual album has Tony Bennett and pianist-arranger Ralph Sharon performing with a group consisting of tenor, trumpet, three trombones, three flutes, vibes, guitar, bass, and such drummer-percussionists as Art Blakey, Chico Hamilton, Jo Jones, Candido, Sabu, and Billy Exner. While the repertoire (swing standards and a few newer pieces including “Lazy Afternoon”) was not unusual, Bennett’s comfort with the instrumentalists is admirable.

#5 – In Person (Columbia, 1958) or Strike Up The Band (Roulette, 1959)

In 1958, Tony Bennett became the first “pop” singer to record a full album with the Count Basie Orchestra; many other vocalists would follow in the 1960s. Bennett made two albums with Basie (one apiece for both of their labels) during 1958-59 and they are equally rewarding. The powerful Basie band proved to be an effective foil for Tony Bennett and there are occasional solos from the notable sidemen.

#6 – I Left My Heart In San Francisco (Columbia, 1962)

The rise of rock and roll made life a little tougher for crooners and veteran pop singers, but Tony Bennett had already gained a great deal of popularity by the mid-1950s and he remained a constant on the pop charts for the next decade. With Ralph Sharon as his pianist and arranger starting in 1957, he had a stable backup trio that was the foundation of his music for the next few decades, particularly in his numerous appearances at nightclubs.

In 1962 Tony Bennett really hit pay dirt with his recording of “I Left My Heart In San Francisco,” the biggest hit of his career. His trademark song is the title cut of a particularly strong album that also includes “The Best Is Yet To Come.”

#7 – I Wanna Be Around (Columbia, 1963)

Tony Bennett was at one of the peaks of his power during the first half of the 1960s. In June 1962, he was featured at a Carnegie Hall concert that found his trio augmented by some top jazz artists (Al Cohn on tenor, guitarist Kenny Burrell and Candido). The resulting Columbia album At Carnegie Hall has the highlights.

The follow-up studio album to I Left My Heart In San Francisco was also quite successful both artistically and commercially, highlighted by “I Wanna Be Around,” “The Good Life,” “Quiet Nights” and “Let’s Face The Music And Dance.”

#8 – The Tony Bennett/Bill Evans Album (Fantasy, 1975)

By the late-1960s, times were tough for many veteran pop singers, at least on records. The record labels, excited by the sales figure of rock, were pushing their solo vocalists to record current pop and rock tunes even if the music clearly did not fit their style. Ella Fitzgerald (who recorded “Hey Jude” and “Sunshine Of Your Love”), Mel Torme, Sarah Vaughan (who was completely off records for several years), Carmen McRae, and others found it difficult to record the high-quality material that they wanted. The situation would not begin to change until the mid-1970s.

Tony Bennett was still riding high on the success of “San Francisco” and in 1965 had luck with “If I Ruled The World,” But within a few years, the pressure from Columbia had greatly increased. 1970’s Tony Sings The Great Hits Of Today was the low point, a rare example of him recording unsuitable material such as “Eleanor Rigby” and “MacArthur Park.” In 1972 after 22 years, Tony Bennett left Columbia. He did not have much better luck being on Verve. Frustrated by being told what to record, he formed his own record company in 1974, Improv.

While it would have been difficult while with Columbia for Bennett to get a release to record an album elsewhere, since he owned Improv, he was able to make the album that ultimately meant the most to him, a set of duets with pianist Bill Evans. Bennett loved Evans’ sensitivity, harmonic sophistication, and ability to embrace melodies while bringing out their inner beauty. The Tony Bennett/ Bill Evans Album, a set of ballads, has Bennett sounded inspired singing such classics as “My Foolish Heart,” “Some Other Time,” Evans’ “Waltz For Debby,” and “Young And Foolish.”

#9 – The Complete Improv Recordings (Concord, 1974-77)

During 1974-77 for his Improv label, Tony Bennett recorded five albums: Life Is Beautiful (with an orchestra arranged by Torrie Zito), Tony Bennett Sings 10 Rodgers & Hart Songs, Sings More Great Rodgers & Hart Songs (the latter two projects with a quartet co-led by cornetist Ruby Braff and guitarist George Barnes), Tony Bennett & Bill Evans Together Again (a second duet album that is the equal of the first), and The McPartlands & Friends Make Magnificent Music (a jazz set with pianist Marian and cornetist Jimmy McPartland). All of the music plus unreleased material was reissued by Concord in this excellent four-CD box set. The different settings and the jazz soloists inspired Bennett although none of these albums had giant sales.

Unfortunately due to the lack of distribution, the Improv label was out of business by 1978. Tony Bennett was at the crossroads of his career. 52 years old, he was very concerned about his shrinking audience, he had a cocaine habit that he soon forced himself to give up, and there was no record deal. Should he retire gracefully?

#10 Bennett Sings Ellington (RPM/Columbia, 1999)

Tony Bennett loved singing too much to ever seriously consider retirement but he needed help. Luckily his son Danny Barrett proved to be a creative businessman and became his father’s manager. Instead of having him play for older folks in Las Vegas, now Bennett went after a younger audience by playing at colleges and hipper clubs. Rather than attempt to be “with it” by singing current material, Bennett enthusiastically performed the classic standards that he loved and which his new audiences were not necessarily familiar with. To them, the Gershwin and Cole Porter tunes sounded like new songs.

After seven years off of records, Tony Bennett returned with triumph in 1986, signing with his old label Columbia and recording The Art Of Excellence. This time around, there was no longer pressure for him to sing rock songs for Bennett had successfully built up a new audience. When he recorded albums that paid tribute to Frank Sinatra (Perfectly Frank) and Fred Astaire (Steppin’ Out), he was not only satisfying his older fans but introducing those artists to the current generation. And his appearance on MTV Unplugged in 1994 (which was a funny irony because his music was always acoustic) gained him many new fans.

There would be no slowdown in Tony Bennett’s career from then on. He was able to perform whatever he liked and in whatever setting appealed to him. In addition to continuing to work with the Ralph Sharon Trio and record now and then with orchestras and jazz greats, Bennett recorded separate full-length albums in which he shared the spotlight with Diana Krall, KD Lang, and Lady Gaga. His Duets and Duets II. albums gave him opportunities to record with many other singers including Amy Winestone; their version of “Body and Soul” made the charts.

Tony Bennett retained most of the power and strength of his voice while in his nineties. His last CD, Love For Sale, was made with Lady Gaga. He did not retire until a week after his 95th birthday in 2021. Were it not for his health problems, one could imagine Bennett still singing the songs he loved when he was 100.

Tony Bennett recorded regularly during his last 35 years. Bennett Sings Ellington from 1999 is an excellent example of the singer in his later years. With his regular quartet and such guests as trumpeter Wynton Marsalis, trombonist Al Grey, and violinist Joel Smiroff, and an orchestra arranged by Jorge Calandrelli, Tony Bennett is heard in prime form on such numbers as “Mood Indigo,” “Caravan,” “Daydream” and “I’m Just A Lucky So And So.”

Although Tony Bennett would probably say that “I’m Just A Lucky So And So” or “The Good Life” could sum up his career, his talent, hard work, and persistence in standing up for musical quality were the real reasons that his music sounds timeless.

Tony Bennett Albums

Photo: MPH Photos /

Scott Yanow, jazz journalist/historian and author of 11 books including The Jazz Singers, The Great Jazz Guitarists, Trumpet Kings, Jazz On Film, and Jazz On Record 1917-76


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