In 1988, guitarist Joe Pass (1929 – 1994), often called “the president of bebop guitar” released an album of songs made famous by Fred Astaire. Pass is generally considered to be one of the greatest jazz guitarists of the 20th century. Born the son of a steel mill worker, he was inspired to play guitar after hearing Gene Autry. He left his home in Johnstown, Pennsylvania to travel with small jazz groups and eventually moved to New York City. After falling victim to drug abuse in the 1950s, he re-emerged in the 1960s releasing a series of influential albums. Downbeat magazine gave their “New Star Award” in 1963 to Pass and he toured with George Shearing and recorded with Les McCann, Frank Sinatra, Sarah Vaughn, and Johnny Mathis. He also spent significant time doing TV and recording session work in Los Angeles during the decade. In the 1970s and early 1980s he recorded six albums with Ella Fitzgerald and won a Grammy in 1975 for The Trio featuring pianist Oscar Peterson and bassist Niels-Henning Ørsted Pedersen. His work was characterized by fluid lines and advanced harmonic concepts associated with saxophone players such as Charlie Parker and John Coltrane, and was an important early improvisational jazz guitar player.

For this 1988 recording of Astaire songs, his record label turned to a classic Hirschfeld drawing of Astaire’s famous “dancing on the ceiling” scene in Royal Wedding, which Hirschfeld had drawn originally in 1951 for MGM to promote the film. Hirschfeld had recently redrawn the image in 1987 for an article in the New York Times, which is where the art director probably saw it. It was the 143rd album Joe Pass had appeared on.