Tony Bennett’s Top Albums, Songs, and TV Appearances

MTV/Everett Collection

Legendary singer Tony Bennett has passed away at the age of 96 after a long battle with Alzheimer’s disease. He reluctantly retired two years ago, after struggling during several performances. Even so, he remained an iconic performer and a very important person in the world of music. Let’s celebrate his life and honor him by going over some of his top albums, songs, and TV appearances during his long career, which began in the ’50s. Of course, we can’t mention every single incredible accomplishment on this list, so be sure to comment some of your favorites as well!

Top Albums

Fifty Years of Tony Bennett


Bennett released over 70 albums during his career! If you’re a fan of Bennett’s smooth voice, you have to pick up Fifty Years – The Artistry Of Tony Bennett (Columbia/Legacy, 1950-2001), which includes 110 of his best songs throughout the decades. If you pick up the five-CD set it also includes a great booklet that goes over his life and career (remember CD booklets? I miss those!) and is a great way for new fans to explore his music as well as pay tribute if you’re a longtime fan.

Tony Bennett Cloud 7


One of his first and perhaps best albums is Cloud 7 (Columbia, 1955). Bennett famously turned down requests for more popular tunes, opting to keep his jazzy feel, and always said that the quality of his songs was very important to him. This album includes hits such as “Because Of You” and “Rags To Riches.”

Tony Bennett Jazz album


Speaking of jazz, whenever Bennett could record with jazz musicians, he jumped at the chance. He did so in Tony Bennett Jazz (Columbia, 1954-67). The album includes collaborations with pianist Herbie Hancock, flutist Herbie Mann, and drummers Elvin Jones and Art Blakey.

Tony Bennett I Left My Heart in San Francisco


We can’t forget the album that housed the biggest hit of his career. I Left My Heart In San Francisco (Columbia, 1962) proved that he could still maintain his spot on pop charts even with the rise of rock and roll in the ’60s. This album also includes the classic hit “The Best Is Yet To Come.”

Top Songs

“Stranger In Paradise”

This song, released in 1952 and taken from the musical play Kismet, reached No. 2 on the Billboard Hot 100 and No. 1 on the Australian charts.

“The Way You Look Tonight”

Couples all over the world will recognize this romantic tune. Bennett had a bit of a career resurgence in the ’90s with an appearance on MTV Unplugged and some collaborations with new artists including the Red Hot Chili Peppers and Elvis Costello. This song was also on the soundtrack for My Best Friend’s Wedding.

“Fly Me To The Moon”

Almost everyone can recognize this song whether they are a fan of Bennett or have never heard of him. While many other artists have covered this song, Bennett’s version is truly stunning and was first recorded in 1965.

“I Left My Heart In San Francisco”

While this song wasn’t the most popular when it was released, it has grown to be one of his most beloved songs. First released in 1962, it has now become one of the most requested songs at weddings.

Top TV Appearances

In his later years, Bennett’s performances with singer Lady Gaga became some of his best. Despite the age difference, the two just worked on stage so well and their voices sound amazing together. Their friendship seemed like something very special.

In the ’50s and ’60s, Bennett was a regular on many variety shows and appeared on The Jackie Gleason Show, The Nat King Cole Show, The Ed Sullivan Show, and even had his own show The Tony Bennett Show.

Like many great performers, he was also invited to perform with The Muppets. He appeared on Muppets Tonight in 1996 and sang with Kermit the Frog.

May he rest in peace.

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May 2019

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