Years of struggle

Sharon and Bennett parted ways in 1965. There was great pressure on singers such as Lena Horne and Barbra Streisand to record contemporary rock songs, and in this vein Columbia Records' Clive Davis suggested that Bennett do the same. Bennett was very reluctant, and when he tried, the results pleased no one. This was exemplified by Tony Sings the Great Hits of Today! (1969), which featured misguided attempts at Beatles and other current songs and a ludicrous psychedelic art cover.

Years later Bennett would recall his dismay at being asked to do contemporary material, comparing it to when his mother was forced to produce a cheap dress. By 1972, he had departed Columbia for MGM Records, but found no more success there, and in a couple more years he was without a recording contract.

Bennett and his wife Patricia had been separated since 1965, their marriage a victim of too much time on the road, among other factors. In 1971, their divorce became official. Bennett had been involved with aspiring actress Sandra Grant since filming The Oscar, and in 1972 they married. They would have two daughters, Joanna and Antonia Bennett.

Taking matters into his own hands, Bennett started his own record company, Improv. He cut some songs that would later become favorites, such as What is This Thing Called Love?, and made two well-regarded albums with jazz pianist Bill Evans, The Tony Bennett/Bill Evans Album (1975) and Together Again (1976), but by 1977 Improv was out of business. A stint living in England, like other American jazz expatriates, did not change his fortunes.

As the decade neared its end, Bennett had no recording contract, no manager, and was not performing any concerts outside of Las Vegas. His second marriage was failing (they would completely separate in 1979, but not officially divorce until 2007). He had (like many musicians) developed a drug addiction, was living beyond his means, and had the Internal Revenue Service trying to seize his Los Angeles home. He had hit bottom.