Rank, Title, Peak Position, Peak Date
1. "I Left My Heart in San Francisco", No. 19, Oct. 20, 1962
Bennett first performed this song in 1962 at the Fairmont Hotel in San Francisco. When Columbia Records released it as a single, it did well, peaking at No. 19, but it managed to stay on the charts for more than eight months. The synonymous album released later that year earned Bennett two Grammy Awards.
2. "I Wanna Be Around," No. 14, March 30, 1963
This iconic song spent 16 weeks on the charts and has been covered by the likes of Frank Sinatra, Peggy Lee, Bobby Darin, and Aretha Franklin. The melody is slow and swaying, but the lyrics are vindictive, musing about wanting to be around when an ex gets their heart broken.
3. "Firefly", No. 20, Oct. 13, 1958
The original track is from Bennett's 1959 album In Person! and was recorded with the Count Basie Orchestra. Bennett also collaborated with Lady Gaga on a version of the song for their joint effort Cheek to Cheek.
4. "The Good Life", No. 18, June 22, 1963
Easily a Bennett standard, this song was featured on four of his top-selling albums. The song stayed on the charts for 10 weeks, and is perhaps one of his most-performed songs. It also serves as the title of his 1998 autobiography.
5. "Who Can I Turn To (When Nobody Needs Me)," No. 33, Nov. 21, 1964
The original song comes from the 1964 musical The Roar of the Greasepaint -- The Smell of the Crowd, but was made famous by Bennett when he recorded it later that year.
Tony Bennett's top five Billboard Hot 100 hits chart is based on actual performance on the weekly Billboard Hot 100, through the Aug. 13, 2016, ranking. Songs are ranked based on an inverse point system, with weeks at No. 1 earning the greatest value and weeks at No. 100 earning the least. Due to changes in chart methodology over the years, certain eras are weighted to account for different chart turnover rates over various periods.