Paul McCartney shares how he was "always frightened of classical music" and what it was like to be a part of the pop world at the time. James Paul McCartney is an English musician, singer, and songwriter. He gained his fame with the Beatles in the 1960s, and then pursued a solo career from 1970 onward.

Actress Julie Andrews comments on the lasting popularity of the Sound of Music 40 years after the film premiered on March 2, 1965 and her relationship with Christopher Plummer after all these years. She also discusses the cast reunion included on the anniversary DVD as well as the other behind the scenes footage she was happy to narrate.

Christopher Plummer, Sound of Music producer by Robert Wise, and screenwriter Ernest Lehman discuss fun facts about the character Captain von Trapp and explain how Plummer got the role. They also remember Plummer's requests in the script and Plummer reminisces about the Austrian food that nearly made him too big for his costume.

Julie Andrews and Christopher Plummer remember the hilarious challenge they faced while filming the last scene of the Sound of Music movie. Andrews played Maria while Plummer was Captain von Trapp.

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.

Ringo Starr comments on his life long friendship with band mate George Harrison and Paul McCartney shares his memory of Harrison's audition to join The Beatles. In November 2001 Harrison passed away after a battle with lung cancer, leaving Starr and McCartney the only surviving Beatles.

Beatle Ringo Starr cries as he remembers the last words George Harrison said to him on his death bed. Harrison passed away on November 29, 2001 after a battle with lung cancer.

The late singer-songwriter Amy Winehouse is interviewed after the release of her 2006 album, “Back to Black,” which won five Grammy Awards in 2008. Hear what Amy thought about when people talked about her addictions and behavior; why she considered herself a “very lucky girl”; and how writing songs about bad experiences helped her to deal with the emotions. Winehouse died on July 23, 2011.

Stevie Wonder interviews with Katie Couric on how Michael Jackson, has inspired him and the rest of the music industry. Stevie Wonder, American musician, singer and songwriter, recalls in his first person account how he never imagined that he would be singing "I Never Dreamed You'd Leave in Summer" at Jackson's memorial service on July 7, 2009. Jackson is recognized as the most successful entertainer of all time by Guinness World Records. He died on June 25, 2009.