Track 4 from To My Wonderful One (1960)

Track 5 from My Heart Sings (1961)

Track 6 from I Left My Heart In San Francisco (1962)

Track 15 from Perfectly Frank (1992)

Tony Bennett began recording in 1951, and released his final album less than two years before his death (his first album, 1952's Because Of You, isn't on streaming services, so I started off the playlist with his second album). So Tony Bennett now holds a number of records for longevity in popular music (longest run of top 10 albums for a living artist, oldest person to release an album of new material, longest span between first and last Grammy nominations). Fittingly, this playlist spans 67 years, with albums from 8 different decades, easily the longest period of time I've covered in a deep album cuts post (the previous record was 57 years for Willie Nelson). 

Bennett recorded over 70 albums, so this obviously doesn't touch everything, but I tried to cover the most artistically and commercially significant albums from each period. The only significant gap in his recording career was when he didn't release any albums between 1977 and 1986, a time, a low point when Bennett had no record deal and nearly died from a cocaine overdose. But in 1986, Bennett began his comeback with The Art Of Excellence and an Oscar-nominated song for the film That's Life! and kept building his momentum up through his unlikely return to platinum records and Grammy awards in the 1990s. 

I've often rolled my eyes at the fact that two artists won Album of the Year for MTV Unplugged albums in the '90s (Bennett and Eric Clapton), it really epitomizes the classic Grammys tendency to cling to comforting reminders of the past. But MTV Live has been playing Bennett's Unplugged heavily the last few days, and it really is a great performance, Bennett deserves a lot of credit for sticking to simple piano trio backing bands and becoming the guy who brought standards into a new era as many of his contemporaries were dying or retiring. I played drums in high school jazz band and also worked as soundman for a friend of mine who gigged around as an old fashioned pop crooner, so I learned a lot about the Great American Songbook at the time when Bennett was the person who was really carrying the torch and managing to seem cool and timeless in the age of grunge and gangsta rap. And his voice really held up amazingly well over the years, gaining some character with age without losing the essence of what made him a star in his twenties. 

At the age of 78, Tony Bennett received the first and only songwriting credit of his entire career when he wrote lyrics to the Django Reinhardt instrumental "Nuages" for the song "All For You." This playlist includes songs written by Duke Ellington ("Azure"), Leonard Bernstein ("Some Other Time"), Oscar Hammerstein ("I Won't Dance"), Cole Porter ("I Concentrate On You"), Kurt Weill ("Lost In The Stars"), and Cy Coleman and Carolyn Leigh ("Rules of the Road," "I Walk A Little Faster," "It Amazes Me").

1970's Tony Sings The Great Hits Of Today! is considered a low point of Bennett's career for a rare attempt to move away from his usual repertoire of jazz standards and Broadway and Tin Pan Alley into contemporary hits. But I have to say, I don't mind hearing Bennett sing some Beatles, Stevie Wonder, and Bacharach & David songs, I like his swinging take on "Here, There And Everywhere." Of course, in more recent decades, Bennett recorded duets with many, many younger stars, most notably on two albums with Lady Gaga, but still largely stuck to classic Bennett material. And the Bennett/Gaga friendship was a really beautiful and touching final chapter of his career.