he won his first grammy award in 1963 for his song i left my heart in san francisco, and performed it on the julie garland show. i left my heart [ applause ] reporter: the crooner s unique voice and timeless style helped him win 19 grammys and two emmys throughout his career. tony bennett, ladies and gentlemen. maybe the best pop singer in the whole world. i asked sinatra why do you think we stayed around so long. and he said because we stayed with good songs. reporter: but the classics weren t always hits. in the 70s, bennett found himself without a recording contract. he was in debt and batting a drug problem. i realized that i thought i was doing well with the drugs, and it i really wasn t. reporter: that s when bennett s son danny stepped in as his manager. bennett resigned with columbia records and began to revitalize his career. he discovered a new audience the mtv generation.