Bing Crosby was, without a doubt, the most popular and influential multi-media star of the first half of the twentieth century, pulling audiences in with his intimate, laid-back voice and innate charm. Narrated by Stanley Tucci and directed by Robert Trachtenberg, this film explores the life and legend of this iconic performer, revealing a personality far more complex than the image the public had only thought they'd known.

Bing Crosby performs with special guests Bob Hope, Marion Ryan, Dave King, Terry-Thomas, and Shirley Bassey.

The program on this DVD is basically a retrospective produced in the early 1990s for public television that was originally called «A Bing Crosby Christmas: Just Like the Ones You Used to Know» that was narrated by Gene Kelly and hosted by Bing's widow, Kathryn Crosby. The program itself features clips from fifteen of Bing's classic television specials, concentrating on the period from the early 1960s onwards when he included Kathryn and their three children in the programs.

Entertainment variety special with Bing and special guests Dean Martin, Bernadette Peters, and Flip Wilson.

Bing Crosby celebrates the holidays by starring in his first color special. This time the show concluded with an extended holiday-themed segment featuring Bing and his guests, Mary Martin, Andre Previn, and The United Nations Children’s Choir.

Bing Crosby's first television special with Jack Benny, Sheree North dropping by to provide a few pointers. Bing sings five tunes, starting with the big production number "Y'all Come!" backed by The Cass County Boys and Jud Conlon's Rhythmaires.

Bing emcees and performs in this special Christmas show packed with guest stars including the cast of Hogan's Heroes, a comedy dog, and more.

The silky-smooth crooner who could sing both pop and jazz performs some of his timeless hits in a rare live concert.

Rosemary Clooney, Michael Feistein, and wife Kathryn Crosby celebrate the voice and singing style of crooner Bing Crosby through clips from his theatrical shorts from the 30s and 40s and archival footage from his television appearances from the 60s and 70s. Such Crosby standards as «Aren't You Glad You're You», «June in January», «Learn to Croon», «True Love» and «White Christmas» are heard.

The Christmas after Bing Crosby's passing, his family gets together to recall all the good times they had. They talk about the people he worked with, how he liked to perform, and ultimately why he had to sing White Christmas at the end of each special.