By Meena
Released in 1962, this signature song won Tony his first two Grammy Awards, it's a timeless love letter to the city.
Image:Canva
This #1 hit from 1951 cemented Bennett's standing as a premier vocalist of the era, a heartfelt ballad showcasing his vocal depth.
Image:Canva
The 1953 chart-topper is a theatrical piece displaying Tony's ability to convey a dramatic narrative through song.
Image:Canva
Bennett's 1965 interpretation of this standard is a celestial delight, showcasing his unique, intimate phrasing.
Image:Canva
This hopeful tune, often used as his concert closer, has resonated with fans since its release in 1962.
Image:Canva
Image:Canva
Released in 1963, Tony's rendition brims with nostalgia, a reminder of the fleeting nature of fame and success.
Image:Canva
From 1964's Broadway show 'The Roar of the Greasepaint', his rendition is powerfully emotive, a masterclass in vocal expression.
Image:Canva
Tony's 1959 interpretation of Charlie Chaplin's classic is deeply moving, a showcase of his ability to connect emotionally through song.
Image:Canva
Tony's 1967 recording is joyfully optimistic, a demonstration of his ability to convey sheer happiness through his performance.
Image:Canva
A poignant 2011 collaboration with Amy Winehouse, this jazz standard showcases an undeniable musical chemistry between two generations.
Image:Canva
Image:Canva