In recent weeks, the world lost an iconic vocalist, jazzman, and entertainer, Tony Bennett.  For many listeners, he is ensconced as one of the great “crooners” alongside Frank Sinatra, Bing Crosby, Sammy Davis, Jr., and others.  But with more than 150 recordings spanning a 70-year career, Bennett holds a unique place in the pantheon of jazz legends.

Though his first professional recordings are virtually forgotten, in 1949 Tony Bennett caught the attention of legendary vocalist Pearl Bailey and, later, Bob Hope, ultimately landing him a contract Columbia Records.  Bennett was immediately popular on Columbia: 1951’s “Because of You” sold over a million copies, “Blue Velvet” topped the charts that same year, and 1953’s “Rags to Riches” spent eight weeks in the number-one spot.

A few years later, Bennett recorded a string of successful records with well-known jazz musicians.  1957’s The Beat of My Heart was popular with both fans and critics, and featured Al Cohn, Nat Adderley, Art Blakey, Jo Jones, and Chico Hamilton, to name just a few.  Follow-up albums Basie Swings, Bennett Sings (1958) and In Person! (1959), featuring a collaboration with the Count Basie Orchestra, were equally well-regarded and arguably laid the groundwork for a favorite Sinatra’s mid-‘60s release, Sinatra at the Sands.  In 1962, it was Bennett who appeared on the inaugural broadcast of The Tonight Show with Johnny Carson.

Though Bennett’s star dimmed for some years with the rise of rock and roll and the British invasion, he recorded two sterling albums with pianist Bill Evans in the 1970s, The Tony Bennett/Bill Evans Album (1975) and Together Again (1976), which are regarded as some of the finest recordings in both artists’ discographies.  Certainly you will hear masterful interpretations of many favorite standards, but check out Bennett’s renditions of Bill Evans staples “Some Other Time” and “Waltz for Debby.”

Bennett’s career experienced a revival in the 1980s, but its most remarkable feature is that it was rooted in the MTV generation.  Always steadfast in his musical vision, Bennett continued to preserve and perform standards and showtunes from the Great American Songbook; but with a twist in marketing led by his son, Danny Bennett, Tony Bennett delivered beloved American music by Cole Porter, Johnny Mercer, Duke Ellington, and George Gershwin to new generations of listeners.  Further, he made that music relevant to new generations, recording/performing with K.D. Lang (A Wonderful World, 2002), Billy Joel (Duets: An American Classic, 2006), Amy Winehouse (Duets II, 2011), and most recently, Lady Gaga (Cheek to Cheek, 2014; Love for Sale, 2021).  For some artists, those sorts of collaborations could be painfully forced marketing ploys – but as Jeff Peckham observed, Bennett’s collaborations were largely successful because each one was earnestly conceived and embraced by Bennett himself.

Of course, Bennett will always be remembered for signature tunes like “I Left My Heart in San Francisco.”  But this month, we celebrate the full breadth of his legacy as one of the great interpreters of American song, an uncompromising artist who insisted on sharing this foundational music with all audiences, and introducing new generations of listeners to music that is the fountainhead of jazz.