Tony Bennett - Ultimate Jazz and Blues (2004)

Through Tony Bennett's long, remarkable career, it's possible to trace the evolution and endurance of vocal pop and jazz in the 20th century. Unlike his idol Frank Sinatra, Bennett was too young to be part of the first wave of the Great American Songbook in the years before World War II. He achieved his national breakthrough in 1951, when the charts were dominated by soft-focused orchestral pop and novelties, music that Bennett himself would often sing during his early years. Occasionally, he was given the opportunity to sing jazz while recording for Columbia in the '50s, but it was a pop song that turned him into a superstar in 1962: "I Left My Heart in San Francisco," a song styled after the classic pop of the pre-war era. "I Left My Heart in San Francisco" turned into an enduring standard of the 20th century but, for a while, its popularity eclipsed that of the singer who popularized the tune. Bennett didn't weather the '60s well, thanks to record companies who attempted to modernize his sound, and while he had an artistically fruitfully '70s on his short-lived independent label Improv, he recorded albums with pianist Bill Evans that established his jazz bona fides he suffered a series of personal problems that left him at rock bottom at the dawn of the '80s. It was then he achieved one of the greatest comebacks in pop music history. Hiring his son Danny as his manager, he reunited with his music director/pianist Ralph Sharon and began targeting younger audiences without shedding his longtime fans. This strategy paid off in the '90s, when 1992's Perfectly Frank topped Billboard's jazz charts and went Gold. Bennett's crossover to the pop mainstream seemed to culminate with 1994's MTV Unplugged, an unexpected hit that took home the Grammy for Album of the Year, but it turned out his revival was no flash in the pan. Bennett stayed in the spotlight until the '90s, not only maintaining his audience but building it through a series of duets with stars as diverse as Lady Gaga and Diana Krall. His partners may have changed along with the times, but through it all, Bennett remained a skilled, charismatic practitioner and vocal advocate for classic American pop.