A List of TV’s Greatest Christmas Specials Over the Years: Frank Sinatra and More

Happy Holidays With Bing and Frank (1957)

For this episode of The Frank Sinatra Show, just as Ol’ Blue Eyes is putting the last candy cane on his Christmas tree, Bing Crosby pops by for a little conversation and a lot of singing! “It’s phenomenal,” says Herbie J Pilato, author of Christmas TV Memories. “Into that half hour they manage to cram in all the major Christmas carols. They even go back in time for some really old, old-time Christmas.”

The Bob Hope Christmas Special (1970)

“Bob Hope was one of the kings of the Christmas specials,” says Pilato. The performer’s 1970 broadcast was taped in front of military personnel at USO stops in Europe and Southeast Asia. It featured guest stars Connie Stevens and astronaut Neil Armstrong and aired without commercials. “Those Bob Hope specials united the country,” notes Pilato, “and helped lessen the trauma of the Vietnam War.”

Bing Crosby’s Merrie Olde Christmas (1977)

The rendition of “Peace on Earth/Little Drummer Boy” sung by Bing on his final holiday special with David Bowie became iconic. “You had two different performers from two different eras with two different styles,” says Pilato. “It was one of the most monumental musical moments in Christmas TV history.”

The Christmas Sonny & Cher Comedy Hour (1973)

Opening with “Jingle Bells,” the stars of The Sonny & Cher Comedy Hour created “one of the slickest and hippest Christmas specials of the time,” says Pilato. Although they would split up the following year, “it showed their warm, affectionate sides.”

The Dangerous Christmas of Red Riding Hood (1965)

This musical retelling of Little Red Riding Hood from the wolf’s point of view stars Liza Minnelli as Red, Australian actor Cyril Ritchard as the Big Bad Wolf, and crooner Vic Damone as the Woodsman. “It’s like Red Riding Hood in a bizarro alternate universe,” says Pilato, who notes that despite the campy concept, Liza, then just 19 years old, “oozed talent.”

The Judy Garland Christmas Show (1963)

“Judy was the first to do a family Christmas gathering on her show,” says Pilato. The Judy Garland Show star also performed “Have Yourself a Merry Little Christmas” and “Somewhere Over the Rainbow.” “One of her guest stars was Jack Jones, who went on to sing The Love Boat theme,” he adds.

The newly-released book, Christmas TV Memories, by Herbie J Pilato with a Foreword by Marlo Thomas, is available for purchase here.