Tony Bennett Photography

Astoria-born singer Tony Bennett kicked off his official recording career in 1952 but proved to be just as popular well over a half-century later. Singing traditional pop standards, big band, jazz, and show tunes, Bennett is the only artist in music history to have new albums chart from his debut through the first two decades of the 21st century.

Throughout it all, some of Bennett’s best known musical gems include “The Good Life,” “I Wanna Be Around,” and of course, his signature song “I Left My Heart in San Francisco.” Outside of his initial rise to fame, this legend also staged several major comebacks, including an MTV Unplugged project in 1994, which earned him a Grammy Award and the respect of an entirely new generation.

That trend continued well into the 2000s as Bennett recorded several Duets albums featuring current and classic trendsetters, such as Aretha Franklin, Josh Groban, and Amy Winehouse. He even teamed with pop superstar Lady Gaga in 2014 for the Grammy-winning Cheek To Cheek collection, which once again debuted atop the charts.