There was a time when variety shows ruled television, and just about any celebrity you could imagine took a spin at hosting one such show at one time or another. The sheer prevalence of the genre meant that Christmas episodes were a no-brainer, and when you pair celebrity variety shows with some of America's favorite singers, you get the birth of the Christmas Crooner TV Special.
There are dozens of specials like these, from classics to forgettable relics, starring legends and would-be legends, and they ran from basically the dawn of television into the 1980s, and even continue now in some forms. When we think of "Christmas crooner TV," though, we tend to think mostly about the 20-year period from the late 1950s to the late 1970s, when the big names were all operating and the format was set. They're dated, to be sure, but there's also something timeless about these shows, a sense of jovial celebration that makes for some wonderful light Christmas viewing.
So, if you're interested in the golden age of Christmas crooners, but you don't know where to start, I've compiled a playlist for you. These are the 10 best Christmas crooner TV specials you can get on YouTube (some of the best are, sadly, no longer easily reached). They're the essentials, the ones that make the perfect starting point for this corner of Christmas pop culture, laid out in a neat row in chronological order. And we begin, unsurprisingly, with Bing Crosby.
"Happy Holidays with Bing and Frank" (1957)
Despite their sometime rivalry and generational gap, Bing Crosby and Frank Sinatra did work together a few times as the pre-eminent crooners of their respective eras, and one of those times is this wonderful half-hour of joyful celebration from the late 1950s, when Sinatra hosted his own variety show. It's a simple enough – Bing comes over to Frank's house and they sing Christmas carols – until the pair drink a holiday punch so potent it transports them back to Victorian times. Then it gets weird, but in a charming way. For a long time, this one was hard to find outside of clips, but Sinatra's estate has since made it available for free on YouTube.
"The Andy Williams Christmas Show" (1963)
Released in the same year as his landmark Christmas album, this edition of "The Andy Williams Christmas Show" has everything you could want from a visit with one of America's most beloved holiday entertainers. There's songs, dancing, a bit with a picnic that's interrupted by Don Knotts in character as Barney Fife, and even some equestrian tricks. But the best part comes when Andy breaks the whole show down, taking time for an "informal" portion of the show to talk to the audience, wrap a gift while ribbing Tony Bennett, and feature the television singing debut of the youngest of the Osmonds, Donny, who makes a meal out of his first major showbiz coup. It's a perfect time capsule of its era and a very well-structured holiday variety show.
"The Judy Garland Christmas Show" (1963)
Judy Garland is not a Christmas crooner. She's a showbusiness icon who happened to do a Christmas special on her variety show in 1963, but because it's, y'know, Judy Garland, I'm counting it. Featuring visits from special guests, dancing from Liza Minnelli, and some very sweet moments with her youngest children, this Christmas special is everything you could want from a legend like Garland, who was near the end of her life (though she didn't know it at the time) but could still give you goosebumps when she launched into "Over the Rainbow" or "Have Yourself a Merry Little Christmas."
"Christmas with the Martins and the Sinatras" (1967)
This is technically a Christmas episode of The Dean Martin Show, but Dino was kind enough to share basically the entire spotlight with his best friend and his best friend's kids. This one's got all the jokes and variety show beats you'd expect, including a duet from Nancy Sinatra and Deana Martin, and of course, Dean and Frank playing with a toy racecar set. It's an essential for Rat Pack fans!
"The Hollywood Palace Christmas Show with Bing Crosby" (1968)
Several times throughout his tenure as King of the Christmas Crooners, Bing Crosby hosted the holiday episode of The Hollywood Palace variety show. They're all worth watching if you're into that sort of thing, but this one is special. Why? Well, it's a fun Christmas show, but also: This is the episode where Bing's kids almost kill their mother with a golf cart, then almost drive that golf cart right off the stage. In a genre with so many carefully choreographed moments, it's a beautifully spontaneous bit of family chaos, which is really what Christmas is all about.
"The Dean Martin Christmas Show" (1968)
If you can only watch one Christmas crooner holiday special, make it this one. There's a reason we chose it for a Heistmas watch party this year. Featuring guest stars like Bob Newhart and Dom DeLuise, and finishing things off with a massive celebrity toy giveaway to orphans and needy kids all over North America, "The Dean Martin Christmas Show" is the platonic ideal of what you want from this kind of thing. It's funny, it's endearing, and it's just anarchic enough (Dino hated to rehearse) to remind you that you're basically just hanging out with your favorite celebrities at Christmas.
"The Andy Williams Christmas Show" (1969)
From 1964 to 1974, Andy Williams hosted a full decade of Christmas specials, and it's really interesting to watch them evolve. The early ones are much more studio audience-based, and it's clear you're watching a Christmas episode of a pre-existing thing. Later, though, Williams opted for a more family-centric approach, literally inviting his singing brothers, his parents, his wife, and his kids to all be part of the action at once. So, we get things like the 1969 Christmas show, where the Williams clan is hanging out on a massive house set complete with truly wild midcentury carpeting, to sing songs, tell jokes, and be as heartwarming as possible. The formula would get a lot of variations in the late 1960s and early 1970s, but Williams nailed it with the '69 edition.
"The Johnny Cash Christmas Show" (1970)
Johnny Cash is not a Christmas crooner, but he did get into the variety show game for a while, and that meant a couple of Christmas episodes eventually made their way out into the world. I'm considering this the wild card entry on this list, because as much as pop culture has flattened Cash's image into the dour "Man In Black" with a troubled past, this Christmas show is, well…it's delightful. There's a lot of country music royalty present, Roy Orbison drops by, and huge chunks of it are just Johnny and his friends sitting around a Christmassy living room set, trading guitars and songs like they didn't really rehearse much but wanted to have fun with it. It's Christmas, but you also get an acoustic country/bluegrass/folk set that includes Cash, Orbison, and the Everly Brothers, along with other legends.
"Perry Como's Christmas Show" (1974)
From 1969 through 1986, Perry Como was Mr. Christmas Special. He put on more seasonal programming ventures than any of the other crooners on this list with the exception of Crosby, who had a head start on everyone else as the "White Christmas" guy. The thing is, I've never had much for Perry Como, and his efforts to chase gimmicks by traveling around the world for his later specials never quite landed with me. This one, though? This is a very good Christmas special from one of the most identifiable Christmas crooners. It's got everything: Peggy Fleming ice skating, special musical guests The Carpenters (who did their own Christmas specials which are also wonderful), and even impressionist legend Rich Little pretending to be Edith Bunker (because it was 1974). It's a delight, and a reminder of just how long Como carried this holiday torch, even as television shifted around him.
"Bing Crosby's Merrie Olde Christmas" (1977)
Bing Crosby is the original Christmas crooner. Through radio broadcasts, holiday records and, eventually, feature films, he became the premiere seasonal singer in American households, and it's a position he held basically from the time "White Christmas" (the song) was first released in 1942.
"Bing Crosby's Merrie Olde Christmas," which sees the singer traveling to England to visit some long-lost relatives, is most famous now for its inclusion of David Bowie, who stops by to duet "The Little Drummer Boy/Peace on Earth" with Crosby, but it's much more than that. The special wasn't produced as Crosby's curtain call, but when he unexpectedly died of a heart attack in October of 1977 at the age of 74, it became his final goodbye to his Christmas fans. And the thing is, you can sort of feel it? It's not that Crosby knew he was going to die, but watching this wonderfully sentimental piece of TV, you get to see a master of the form near the end of his life, looking not forward but back, pondering what it all means and what he really wants to remember. The tone of it, coupled with Crosby's death, all make it feel like the end of the Christmas Crooner Golden Age. It's a closing of the book, and therefore a great way to end this list.
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