A very young looking Frank Sinatra appears on television for the first time on May 27, 1950, trading jokes and barbs with Bob Hope on the latter’s television show. Already well established as a singer, Sinatra made his presence known in Hollywood when he won the Academy Award for Best Supporting Actor in 1953 for his role in From Here to Eternity.

Clive James interviews Sinatra about his love for singing and the video shows clips from opening acts and a song from Sinatra who is called the “most famous man in the world.” In 1988, Frank Sinatra travels to Australia to perform at the Sanctuary Cove concert, 14 years after he vows never to return to that country because of negative comments about him in the press.

Fellow entertainers attend Frank Sinatra’s memorial, with Wayne Newton, Debbie Reynolds, Joey Bishop and more talking about Sinatra’s legacy. Historian Rick Ross also chimes in and Jerry Lewis is a noted no-show. Sinatra, a singer and actor, died on May 14, 1998 and was eulogized by his son, Frank Sinatra, Jr.

Bill Newcott interviews Frank Sinatra, Jr. for My Generation inside the Capitol Records building in Los Angeles where Frank Sinatra recorded much of his music. The two discuss some of Frank’s more famous friends, including Dean Martin; how the world of music changes in the 1960s with Elvis Presley’s music plus the British Invasion; how Frank Sinatra, Jr. served as his father’s musical director for the last 7 years of his concert performances; and more.

Watch interviews with Bing Crosby's daughter, nephew, biographer, and even Michael Bublé on how Crosby changed the music industry and greatly influenced Frank Sinatra. At the 13:11 mark in the video, Gary Giddins, Crosby's biographer, talks about how Crosby accidentally began the tradition of selling Christmas music to the public around October with "White Christmas."

Bing Crosby passed away on October 14, 1977.