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.

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.

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.

Actor Kevin Costner, known for his role opposite Whitney Houston in The Bodyguard, remembers the emotions he felt during her funeral and reflects on their working relationship. Houston passed away on February 11, 2012 with her funeral held on the 18th. It was attended by many of her celebrity friends and peers like Stevie Wonder, Alicia Keys, R. Kelly, and many more.

Singer Aretha Franklin reflects on the relationship she had with Whitney Houston from their first meeting when she was a child to their musical collaboration in 1989 and discusses the ups and downs of Houston's success throughout her life. Franklin was a close friend of her mother, Cissy Houston, but the singer could not attend Houston's funeral after she passed away on February 11, 2012.

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.

Songbird Whitney Houston reminisces about when her mother, Cissy, sang with the Sweet Inspirations as a back-up for Elvis Presley, both in the recording studio and on tours, starting in 1969. Find out what lavish outfit Presley was wearing when Houston first met The King and how she reacted to being in his presence. Sweet Inspirations also sang the backup vocals for Aretha Franklin.

Jack Lemmon, an Academy Award winning actor and musician, discusses Marilyn Monroe and her insecurities during her rise to fame. Lemmon starred in Some Like It Hot with Marilyn Monroe in 1959 and saw her experiences and insecurities in Hollywood in the 1950's and early 1960's first hand.