Jack Jones

By many measures, Jack Jones was the most popular crooner to emerge between the heyday of Elvis Presley and the rise of the Beatles. In the span of two years, he snagged two Grammys for Pop Male Performance -- "Lollipops and Roses" in 1962 and "Wives and Loves" in 1964 -- which was enough to lay a foundation for a career that lasted well into the 21st century. Although his charting hits dried up in the early '70s -- prior to that, he was a fixture on the Adult Contemporary charts, racking up such number one hits as "The Impossible Dream (The Quest)" -- he continued to perform in Las Vegas and on the road, making the occasional foray into pop culture, like when he sang "The Love Boat Theme" in 1980. In his later years, he gravitated toward blues and jazz, releasing ArtWork, a collaboration with Joey DeFrancesco, in 2023.