Frank Sinatra, multi-talented entertainer
Hollywood, December 1957
Series: The Frank Sinatra Show
Episode: “Happy Holidays with Bing & Frank” (Episode 1.10)
Air Date: December 20, 1957
Director: Frank Sinatra
Wardrobe Credit: Morris Brown
Tailor: Sy Devore
Happy birthday, Frank Sinatra! To celebrate the 103rd anniversary of Ol’ Blue Eyes entering the world in a Hoboken tenement, let’s look back at a time when Frankie was sittin’ on top of the world: the late 1950s.
After the low point of his life and the prospect of his career in ruins, Sinatra bounced back with an Academy Award-winning performance in From Here to Eternity (1953) and a seven-year recording contract with Capitol Records that yielded an impressive string of concept albums that remain among the best popular music ever recorded.
Sinatra was one of the biggest stars of the world in 1957 when ABC signed him to a $3 million contract for The Frank Sinatra Show, a variety and drama series for which Sinatra would have almost total artistic freedom.
As the Chairman of the Board was a lifelong Christmas fanatic, it was unquestioned that the series would feature a special holiday episode, which Sinatra himself stepped up to direct, though he knew the show would need a guest worthy of the season he loved.
“He was a guerilla, if he wanted to direct, [he would direct],” said the show’s producer William Self during a 2003 Q&A at the Museum of Television & Radio (MT&R) after the show was unearthed. “It was Frank’s idea to do a Christmas show with Bing. He respected Bing a great deal… they got along great, and Frank just said, ‘I’m gonna direct it,’ and I said, ‘Yes, sir!'”
A year after their success together in High Society, the 1956 musical remake of The Philadelphia Story, Bing Crosby joined Frank for the half-hour special episode. Both stars were big enough to work their own preferred way, so the musical “duets” were recorded ten hours apart to accommodate Bing’s preference for pre-recording in the morning and Frank’s preference for live recording in the evening.
“Nobody embraced Christmas as he did,” Nancy Sinatra told Variety of her father’s love for the holiday season. It was Nancy who unearthed the original 35mm film print of the holiday special while she was looking through disintegrating items in the family vault.
“I think this show exemplifies that he loved this time of year,” said Tina Sinatra, Frank’s youngest daughter, during the same MT&R Q&A, though both daughters dispute that Frank would ever live in what Tina described as a “bachelor’s lair” as Nancy pointed out that he would have hated all of the green on the set,from the mint-colored Royal typewriter to the bright green horse that would later be used on the set of The Brady Bunch.
“You see how neat Dad was with the trimming of the tree? Forget it,” Nancy explained to the audience of the 2003 Q&A, demonstrating Frank’s real-life method of haphazardly throwing tinsel on a tree.
“That was only once… it was late he got tired,” argued Tina.
“…and drunk,” added Nancy, to a knowing audience’s laughter.
“Happy Holidays with Bing and Frank” aired Friday, December 20, 1957 on ABC. The warm half-hour program includes many genuine moments, such as Sinatra accidentally dropping an ornament while trimming the tree during the opening number, “Mistletoe and Holly”. Despite producer William Self wanting to reshoot the scene, Frank merely shrugs off his clumsiness, casually bending down to pick it up before re-hanging it on the tree, adding a touch of authenticity that makes viewers feel like me may be watching the real Frank Sinatra decorating his home for the holidays… albeit while dressed impeccably in a blazer, cuff links, and silk tie in the well-lit Samuel Goldwyn Studios in West Hollywood.
What’d He Wear?
Sinatra dresses sharply for an evening of holiday entertainment, though his three-button navy blazer and gray flannel trousers recalls a similar look he wore in Pal Joey (1957), released just two months earlier.
Frank’s dark navy wool blazer was almost definitely tailored by Sy Devore of Beverly Hills, the go-to tailor for the Rat Pack as well as gents in their orbit including Bing, Nat King Cole, Bob Hope, Jerry Lewis, Elvis Presley, and John Wayne. It’s a darker shade of blue than the blazer he wore earlier that year in Pal Joey, and this particular jacket has silver crested shank buttons rather than the gold buttons on the Pal Joey blazer. Frank fastidiously wears the blazer with the top two buttons fastened, leaving the third correctly undone. There are also three smaller matching buttons on each cuff.
The ventless blazer has notch lapels, straight flapped hip pockets, and a welted breast pocket for his neatly folded white linen pocket square.
“He was crazy about his ties—only silk would do, in muted patterns or dignified stripes,” writes Bill Zehme in The Way You Wear Your Hat: Frank Sinatra and the Lost Art of Livin’, the definitive guide to the Chairman’s sense of style. “He favored the feel and designs of Sulka, which he learned from George Raft, who wore Sulka everything. Turnbull & Asser impressed him as well.”
Nancy Sinatra apparently inherited her father’s eye for neckwear, vigorously noting during the 2003 Q&A that the restoration made his tie look grayer than the bold blue it was in real life.
“Fancy ties and grandma’s pies, and folks stealin’ a kiss or two,” croons Frank as he rubs the shiny satin of his blue cravat during “Mistletoe and Holly”. When he later repeats the verse, he actually pulls the tie out of his blazer to reveal that the right side of the bottom down to the blade is a lighter shade of blue, creating an asymmetrical “dipped” effect.
When not wearing a tuxedo for the evening, Frank seemed to prefer keeping his evening ensembles as close to black tie with dark (but never brown) suits and sport jackets worn over plain white shirts. His white cotton shirt in the Christmas special has a large point collar with a shapely, semi-spherical curve over the tie space. Behind-the-scenes shots illustrate that the shirt buttons up a plain front and has a monogram on the left breast.
Naturally, the shirt also has double (French) cuffs for Frank’s required cuff links. “Cuff links were, of course, required always,” writes Zehme, who recalls family anecdotes about the Chairman’s two drawers for cuff links alone. “He got them everywhere, but especially loved to buy them from a Florida hustler named Swifty Morgan.”
The flat gold square links that Sinatra wears on his cuffs for this special Christmas episode are consistent with the elegant minimalism of the rest of his outfit. Whether or not they were purchased from the questionable Mr. Morgan is lost to history.
While Frank Sinatra paid attention to how he dressed, he was hardly a flashy dresser. In fact, the most affected piece of his wardrobe in this particular episode was his subtly monogrammed belt buckle, a silver pinhead-textured box-style buckle with “FS” embossed in the upper left and lower right corners, respectively.
Navy blazers and khaki slacks have become something of an easy go-to ensemble for gents looking for a shortcut to dressing well. While there’s nothing inherently wrong with that combination, I prefer the more classic balance of dark gray wool trousers with a navy blazer. Frank sports a pair of dark gray flannel trousers that, combined with the double reverse pleats and the fashionably full fit of the late ’50s, look voluminous on the slim singer’s frame. They have side pockets and are finished with turn-ups (cuffs) on the bottoms.
“There was no excuse for brown shoes past sundown, ever,” writes Zehme. “To emphasize his convictions, [Sinatra] was not above inserting lit firecrackers into the brown shoes of any comrade.” Keeping this in mind, it’s no surprise that Frank wears a pair of black calf cap-toe oxfords and black socks with his ensemble.
While his guest had the presence of mind to wear black shoes for his appearance on the show, one wonders how Frank must have seethed at Bing’s decision to appear on his evening-set Christmas special wearing a brown suit.
Frank wasn’t as much of a jewelry enthusiast as his fellow Rat Packer Sammy Davis Jr., but he would occasionally wear a ring on his right pinkie, whether it was the signet ring with his family crest or one of the matching diamond rings he had made for him and Dean Martin. The ring worn in this special appears to be a different one altogether with a large black surface.
Well, Merry Christmas, ladies and gentlemen, and welcome to our Christmas show for Bulova—the gift of a lifetime—and Chesterfield—my cigarette.
The Frank Sinatra Show was proudly sponsored by Bulova and Chesterfield and, though Ol’ Blue Eyes was almost definitely reading from cue cards for the above opening to the episode, he was certainly a confirmed Chesterfield smoker during this era before he switched to Camels for his Reprise years and beyond.
Could his watch possibly be a Bulova then? The show certainly makes a case for it as the first part of Frank’s clothing we see is his gold wristwatch, strategically positioned with the round silver dial gleaming from the inside of Frank’s wrist as he trims his tree.
Founded in New York City by Bohemian immigrant Joseph Bulova in 1875, Bulova has been a steady presence in the American watchmaking scene for nearly 150 years, breaking ground not only for its technical innovations but also its marketing savvy. Bulova produced the first-ever advertisement broadcast on radio (1926), followed by the first-ever TV advertisement fifteen years later (1941).
Now owned by the Japanese conglomerate Citizen Watch Co., Bulova continues to make men’s watches that pay homage to its mid-century reputation, particularly the Classic Collection. If you’re looking for the simple elegance of Frank’s gold case, silver dial, and dark leather strap, check out the Aerojet (also on Amazon) or the Surveyor, both available for under $250.
A brief “fantasy” sequence finds the two crooners joining the carolers for a brief—and unquestioned—transportation back to Merry Olde Victorian England, where they merely supplant their 1957 outfits with ulsters, scarves, and felt toppers to fit in with the Ralph Brewster Singers.
Frank may have been known for the way he wore—and cocked—his hats, and you have to admit that he brings more swagger to a felt top hat than one might expect.
What to Imbibe
Frank: Bingo, can I offer you a little toddy?
Bing: Ah, a little toddy for the body might just take the chill off. What are you featuring here tonight, Frank?
Frank pours “a little jazz” for himself and Bing as they launch into a fun “Jingle Bells” duet, though it isn’t until the song is over that we hear Frank explain “what’s going on in the tub here.”
Our host is quick to clarify that the “tub” full of apples that Bing refers to is actually “an old English wassail bowl,” and that the two are thus imbibing in wassail. Frank claims the recipe is hundreds of years old (he’s not wrong) before bemusing about the “wonderful time in merry old England,” which of course inspires our crooning heroes to saunter outside and join a group of Victorian-era carolers.
Wassail? What’s that?
In short, it’s a hot, mulled cider punch that originated in England during the Middle Ages as part of a yuletide ritual for luck in the coming year’s harvest. The ritual itself is known as “wassailing”, which was typically observed on Twelfth Night (January 5 or 6). The traditional Christmas carol “Here We Come A-wassailing” (Americanized to “Here We Come A-caroling”) celebrates this practice and the spirit of generosity as the rich would offer up the contents of their wassail bowl to carolers that arrived at their door with cheerful songs promising good fortune.
The earliest known wassail was actually a drink called “lambswool” that consisted of warmed mead with roasted crab apples dropped in and bursting. By the 1600s, the drink evolved to a mulled cider spiced with cinnamon, ginger, nutmeg, and sugar, and topped with slices of toast for sopping. Modern recipes have extra spirits—often with a base of wine, brandy, or sherry—and are topped with apples and oranges, perhaps in tribute to the original crab apples of the lambswool recipe.
According to “We Two Kings”, the tenth season holiday-themed episode of Frasier, the bowl itself is integral to the definition of its contents.
Martin: Why don’t you just use the punch bowl?
Frasier: Because then it wouldn’t be wassail, it would be punch.
Fed up with his pretentious son, Martin consults the dictionary for a clearer definition of wassail and learns that it is merely defined there as “a Christmas punch.”
Our old friend, Mr. Bing Crosby, will be our guest, and the accent is on music, both traditional and modern… and here’s one of the newer songs…
Frank doesn’t mince words when beginning his holiday show. After the first sentence mentioning his sponsors, he spends the next sentence introducing his guest, the show’s focus, and the first song, “Mistletoe and Holly,” for which he shares a writing co-credit.
Bing himself shows up after the song, joining Frank in a short a capella round of “Happy Holiday,” an Irving Berlin tune that Bing himself had introduced in the 1942 film Holiday Inn:
Bing: Say, that must be your key.
Frank: This is my ballpark!
The good Mr. Crosby comes bearing gifts, including his own recent Christmas album, A Christmas Sing with Bing Around the World. In turn, Frank hands him “a jolly group of Christmas songs… by me.”
While Bing had recorded plenty of holiday-themed albums by the time of the special, A Jolly Christmas from Frank Sinatra was Frank’s second holiday record but his first full-length holiday album was his 1948 album, Christmas Songs by Sinatra, had been originally released by Columbia as a 78 rpm album set and a 10″ LP record.
Recorded in the decidedly non-wintry setting of Los Angeles in the early summer of 1957, A Jolly Christmas from Frank Sinatra consists of twelve holiday tracks featuring Frank backed by an orchestra conducted by Gordon Jenkins, who also arranged the music for the album. Choral backing is provided by the Ralph Brewster Singers, who also appeared as the Victorian-era carolers in this special. The album was first released on September 21, 1957, though the CD reissue 30 years later included two bonus tracks: the 1954 single versions of “White Christmas” and “The Christmas Waltz”, the latter being one of my personal favorites.
The entire playlist for the “Happy Holidays with Bing & Frank” special:
- “Jingle Bells” (Instrumental)
- “Mistletoe and Holly” (Frank Sinatra)
- “Jingle Bells” (Frank Sinatra & Bing Crosby)
- “Deck the Halls” (The Ralph Brewster Singers)
- “God Rest Ye Merry Gentlemen” (Frank, Bing, and The Ralph Brewster Singers)
- “Hark the Herald Angels Sing” (Frank, Bing, and The Ralph Brewster Singers)
- “O Come All Ye Faithful” (Frank, Bing, and The Ralph Brewster Singers)
- “The First Noel” (The Ralph Brewster Singers)
- “It Came Upon a Midnight Clear” (Frank Sinatra)
- “Away in a Manger” (Bing Crosby)
- “O Little Town of Bethlehem” (Frank Sinatra & Bing Crosby)
- “Rudolph the Red-Nosed Reindeer” (Bing Crosby)
- “Santa Claus is Coming to Town” (Frank Sinatra)
- “The Christmas Song” (Frank Sinatra & Bing Crosby)
- “White Christmas” (Frank Sinatra & Bing Crosby)
How to Get the Look
The Chairman of the Board illustrates the classic navy blazer’s versatility for holiday get-togethers, whether you’re dressing for a party or a one-on-one musical dinner with a respected pal.
- Dark navy wool single-breasted blazer with 3 silver shank buttons, welted breast pocket, straight flapped hip pockets, 3-button cuffs, and ventless back
- White cotton shirt with large point collar, plain front, breast monogram, and button cuffs
- Blue satin silk tie with light blue “dipped” blade
- Dark gray flannel double reverse-pleated high-rise trousers with belt loops, slanted side pockets, button-through jetted back pockets, and turn-ups/cuffs
- Black leather belt with textured silver monogrammed box buckle
- Black calf leather derby shoes
- Black socks
- Bulova yellow gold wristwatch with silver dial on black leather strap
Do Yourself a Favor and…
You can also read more about Frank’s daughters Tina and Nancy celebrating their father’s legacy and love of the holidays in this article written by Chris Willman last December for Variety.