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Jack Daniel's Releases Frank Sinatra-Inspired Premium Whiskey

Jack Daniel's Releases Frank Sinatra-Inspired Premium Whiskey

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The Sinatra Select is a toast to Ol' Blue Eyes' favorite drink

No one quite enjoyed their Jack Daniel's more than swoon-worthy singer Frank Sinatra. Now, Jack Daniel's is returning the love in the form of a premium whiskey, Sinatra Select.

The Sinatra blend was aged in "special Sinatra barrels" at the Lynchberg, Tenn., distillery, and is a darker amber color than the tradtiional Jack Daniel's, reports the Associated Press. Jack Daniel's announced the special-edition bottle this week, the Associated Press reports. The bottle will be in airport retailers, starting in the Las Vegas airport Dec. 1 and then moving to 200 other airports and high-end retail stores.

The Sinatra-whiskey association is no secret to Sinatra fans; Sinatra would call it "the nectar of the Gods" and often had the drink in hand while performing. "This fine Tennessee Whiskey, or Old No. 7 as he referred to it, was a favorite part of my father's life and he loved both sharing it with his friends and introducing it to new acquaintances," said Sintra's son, Frank Sinatra Jr., in a press release.

Frank Sinatra-Inspired Jack Daniel’s Whiskey

In our books, Frank Sinatra epitomizes bossed-up gentlemen swag. As in, who else could croon like a baby angel, make women swoon with a sly wink, kick it on the reg with Reagan and swig back whiskey like nbd…all at the same time? Bieber Fever, PSH, get outta here.

Jack Daniel’s is honoring Sinatra’s legacy with a premium version of his all-time favorite whisky. Jack Daniel’s Sinatra Select is aged in unique “Sinatra barrels” located at the liquor brand’s Tennessee distillery. The new rendition consists of a darker amber color than the original Jack Daniel’s, acquired by exposing the spirit to extra layers of toasted wood within the barrel. A smooth vanilla taste with hints of spice and oak are present.

Jack Daniel’s Sinatra Select will be making its debut at the Las Vegas Airport on December 1st, followed by releases at major airports worldwide and high-end retail stores within the United States. The special-edition whiskey is packaged in an exclusively designed 1-liter glass bottle and projected to be priced at $150 per unit. Fittingly, for high rollers only.

Jack Daniel’s Announces Sinatra Century In Celebration Of Frank Sinatra’s 100th Birthday

The Jack Daniel Distillery has announced the nationwide release of Jack Daniel’s Sinatra Century, the brand’s latest collaboration with the Sinatra Family to celebrate The Chairman of the Board’s Centennial. On shelves now, Sinatra Century is the latest ultra-premium whiskey from the Jack Daniel’s family to commemorate Jack and Frank’s special friendship. As a limited edition expression, only 100 barrels of Jack Daniel’s Sinatra Century are being made available in individually numbered bottles making each as unique as the man to which it’s attributed.

The relationship between Frank Sinatra and Jack Daniel’s is legendary, special and authentic and one that still holds strong to this day. First recommended by friend Jackie Gleason , the Tennessee Whiskey quickly became Sinatra’s signature drink. During performances, he kept a glass of Jack Daniel’s on a nearby stool on stage. It was his drink of choice at bars in his favorite cities, Las Vegas , Palm Springs , Chicago , Miami and (of course) New York.

Master Distiller Jeff Arnett created Sinatra Century through the careful selection of specially crafted barrels. Tasting his custom selections with the Sinatra family, he sought a bold, refined flavor that is befitting Sinatra’s legacy.

“At the Jack Daniel’s Distillery in Lynchburg , we worked very hard to achieve a special flavor and aroma for Sinatra Century in order to give Frank a proper 100 th birthday gift,” says Arnett. “This meant working with the people who knew him the most, his family, and honoring the legacy that he has shaped with our brand. We have created a product that we know the public will love just as much as Frank did.”

Like all of Jack Daniel’s expressions, Sinatra Century is crafted using the same cave spring water from the Jack Daniel’s Hollow, proprietary yeast and charcoal-mellowing process that’s been used in the distillery’s nearly 150-year-old Tennessee Whiskey recipe. From there, the whiskey enters specially selected “Sinatra” barrels hand-picked by Master Distiller Jeff Arnett. In those barrels, the liquid is exposed to extra layers of perfectly toasted oak through a grooving process only done at the Jack Daniel’s Cooperage.

Commenting on Jack Daniel’s Sinatra Century, Frank Sinatra Jr. explains, “Sinatra Century is a fitting tribute to Dad and the perfect way to mark his centenary in December. Jack Daniel’s was Dad’s drink of choice, whether entertaining friends, or making new acquaintances. Therefore, it only seems right that we raise a toast of Sinatra Century to the musical legend as we celebrate what would have been his 100th birthday this year.”

Sinatra Century, at 100 proof, is the Jack Daniel Distillery’s second offering to commemorate Frank Sinatra . The first was Jack Daniel’s Sinatra Select. Jack Daniel’s Sinatra Select was introduced in 2013.

This one-time, limited release of Jack Daniel’s Sinatra Century is available now and will be the only available selection of the whiskey at an approximate retail price of $499.99 per 1L.. Each exclusive bottle will be enclosed in a luxury gift box inspired by the legendary singer’s signature style. Additionally, the set will also offer a selection of previously unreleased Sinatra tracks, entitled “Sinatra Live at the Sands in 1966,” to accompany the specially designed Jack Daniel’s Sinatra Century bottle.

You can also pay tribute to Sinatra with a specialty drink created by mixologists at one of the entertainer’s favorite haunts, Fontainebleau Miami Beach. The Chairman of the Board cocktail features Jack Daniel’s Sinatra Select (or Century).

Chairman of the Board

  • 1.5 oz. Jack Daniel’s Sinatra Select
  • 1 oz. Aperol
  • 1 oz. Carpano Antica
  • 2 dashes Orange Angostura Bitters

Place ice cube in rocks glass
Add Jack Daniel’s Sinatra Select, Aperol and Carpani Antica directly to glass
Add two dashes orange bitter into glass and stir
Garnish with an orange twist

Gentleman Jack

If Black Label is the iconic Tennessee whiskey, then Gentleman Jack is its more sophisticated and refined big brother. Initially released in 1988, Gentleman Jack was the first new bottling produced by the brand in decades.

The whiskey used to produce Gentleman Jack is sourced from barrels resting on the lower levels of the aging house. Instead of being charcoal-mellowed once, Gentleman Jack is slowly dripped through the sugar maple charcoal twice, a process that distinguishes it from the others. This results in an eminently sippable and sophisticated whiskey bottled at a smooth 40 percent ABV (80 proof).

Jack Daniel's Releases Frank Sinatra-Inspired Premium Whiskey - Recipes



are registered trademarks of Jack Daniel’s Properties, Inc.

Distilled and Bottled by Jack Daniel Distillery, Lynchburg, Tennessee. ©2021 Jack Daniel's. All rights reserved.

All other trademarks and trade names are properties of their respective owners.


Please do not share or forward with anyone under the legal drinking age.


Together the Two Tennessee Distilleries Have Pledged $5 Million to Advance African American Leadership in Whiskey

LYNCHBURG, TN – The Jack Daniel Distillery and the Nearest Green Distillery announced today the Nearest & Jack Advancement Initiative to further diversity within the American whiskey industry. Both companies are supporting it equally with an initial combined pledge of $5 million to help create the Nearest Green School of Distilling, develop the Leadership Acceleration Program (LAP) for apprenticeships and establish the Business Incubation Program (BIP), focused on providing expertise and resources to African Americans entering the spirits industry as entrepreneurs. This joint initiative will be guided by an advisory board with members from both organizations.

Motlow State College, the fastest growing college in Tennessee, has worked with leaders from both companies for the past year to develop a curriculum for the Nearest Green School of Distilling. The STEM based and employable skills focused program has passed Motlow State requirements and is now awaiting approval from the Tennessee Board of Regents to begin moving toward accreditation by the institutions accrediting body SACSCOC. The certificate program may be offered as early as Fall 2021.

The Leadership Acceleration Program (LAP) will offer apprenticeships specifically to African Americans already in the whiskey industry, who are wanting to become a head distiller, head of maturation or production manager. The inaugural apprentices have already been identified and will begin shadowing at top distilleries throughout the country.

The third arm of the Nearest & Jack Advancement Initiative is the Business Incubation Program (BIP) that will offer African American entrepreneurs mentorship in all areas of the distilling business, including access to top marketing firms, branding executives, expanded distribution networks and other assets and opportunities to grow their spirits businesses.

“Generally, when companies talk about the need to improve diversity, few immediate action steps follow,” said Fawn Weaver, CEO, Uncle Nearest Premium Whiskey . “Our group is different. We are doers, and we all agreed to work together to improve diversity in our industry, and specifically, a way to get African Americans into top positions within our industry. Nearest Green taught Jack Daniel how to make Tennessee whiskey and we’re incredibly proud our companies are joining forces to further their legacies of excellence, and to make distilling and the whiskey industry we love more diverse.”

“Given our deep commitment to diversity and inclusion, I am thrilled we are coming together in this way today,” said Lawson Whiting, President and Chief Executive Officer, Brown-Forman Corporation, the parent company of Jack Daniel’s. “This collaboration allows the extraordinary friendship of Nearest and Jack, and the hope they embodied during racially divided times in our country’s history, to help us advance the next generation of African American leaders in our industry.”

Uncle Nearest Premium Whiskey, independently owned by CEO Fawn Weaver, honors the first known African American master distiller, Nathan “Nearest” Green. It is the most awarded American whiskey of 2019 and 2020 to-date, garnering more than 65 awards in the past 16 months, including Double Gold at the 2020 San Francisco World Spirit Competition and back-to-back honors of "World's Best" at Whisky Magazine’s 2019 and 2020 World Whiskies Awards in New York and London. Uncle Nearest has also earned more than 20 Best in Class honors, including Cigar & Spirits Magazine naming Uncle Nearest one of the “Top 5 Whiskies in the World.”

The whiskey is currently available in all 50 states and 12 countries (while shipping into a total of 148 countries), in more than 12,000 stores, bars, and restaurants, and at its 270-acre distillery in Shelbyville, Tenn., dubbed by a member of the press as “Malt Disney World.” For more information please visit the Uncle Nearest website , and follow on Instagram and Facebook @unclenearest.

Frank Sinatra turns 100, so let's celebrate


Slip on your smoking jacket, pour your favorite beverage and join Jeffrey Lee and Tom as they go all Draper and Sterling in the basement. (Video by Scott Utterback, The Courier-Journal)

The Honey Trap is one of six specialty cocktails Doc Crow's has created for Frank Sinatra's 100th birthday. (Photo: Courtesy photo)

"Alcohol may be man's worst enemy, but the bible says love your enemy."

And we say love Frank Sinatra, the singer/actor with a well-documented affinity for Jack Daniel's, whose 100th birthday will be celebrated at bars nationwide this weekend.

At Doc Crow's, 127 W. Main St., head bartender Keri Smith has conjured up a special cocktail menu featuring six Jack Daniel's-based drinks with Sinatra-inspired names, from Old Blue Eyes to His Way. The cocktails — along with Jack Daniel's Sinatra Select, a 90-proof whiskey made in specially charred "Sinatra barrels" — will be available from 5 to 11 p.m. Saturday.

"Why not?" said Smith, a proclaimed Rat Pack fan. ". It's another reason to drink on a Saturday in Louisville."

At 8UP, 850 W. Chestnut St., beverage director Clay Livingston has also created a range of specialty cocktails featuring Jack Daniel's, including the tiki-style Summer Wind and New York, New York, a version of a Manhattan. Try the cocktails from 4 p.m. to 2 a.m. Saturday.

Don't panic! We've got your bourbon gift list

For those who can't make it out, Smith has offered up several cocktail recipes to make at home. But if you're looking for something a little more authentic, try Sinatra's signature drink — Jack Daniel's on the rocks, with a splash of water.

Specialty cocktails at Doc Crow's has created (Photo: Courtesy photo)


  • 1 ounces Jack Daniel's Tennessee Honey
  • 1/2 ounce simple syrup
  • 1/2 ounce lemon juice
  • Sparkling wine
  • Lemon peel

In a small shaker filled with ice, combine the whiskey, simple syrup and lemon juice. Shake and double strain into a champagne flute. Top with sparkling wine. Express the oils from the lemon peel into the drink and garnish with the remaining peel.


  • 1 teaspoon sugar
  • 1 teaspoon cinnamon
  • 1 ounce Jack Daniel's Tennessee Fire
  • 1 ounce Buffalo Trace Bourbon Cream

Combine the sugar and cinnamon until mixed. Place on a plate and dip a shot glass in the mixture so it coats the rim. Combine the remaining ingredients in a small shaker tin with ice. Shake and strain into the shot glass.

Rye releases Advent Cocktail Calendar


  • 1 1/2 ounces Jack Daniel's Tennessee Whiskey
  • 3/4 ounce lemon juice
  • 1/2 ounce simple syrup
  • 1/2 ounce Blue Curacao
  • Splash of lemon lime soda

Combine the whiskey, lemon juice, simple syrup and Blue Curacao in a small shaker. Add ice and shake. Strain into a Collins glass. Add a splash of lemon-lime soda and top with ice.

Review: Jack Daniel’s Sinatra Select Tennessee Whiskey

Jack Daniel’s often does special releases for Duty Free/Travel retail and it’s nice to see one of them, the Jack Daniel’s Sinatra Select Tennessee Whiskey make its way into a full retail offering. Jack Daniel’s Sinatra Select Tennessee Whiskey is a special expression of Jack Daniels which is made from a blend of spirit aged in special “Sinatra barrels” and classic Jack Daniel’s Old No. 7 Tennessee Whiskey. A Sinatra Barrel is one where the the staves in the barrel are grooved, which directly exposes the whiskey to the deep red layer (the part of the barrel where much of the color in whiskey comes from). The result of using grooved staves is much more barrel impact than you’d see with the standard Jack Daniels release. In addition to using special barrels, the Sinatra Select Whiskey is released at 90 proof, which is Jack Daniel’s original proofing (it was lowered from 90 proof in 1987 to 86 and then lowered again in 2002 to 80 proof).

Jack Daniel’s Sinatra Select Tennessee Whiskey (45% ABV, 90 Proof $165 per 1 Litre) – having more contact with the core of the barrel has given this whiskey a darker and depper amber color than the standard Jack Daniel’s. The extra wood contact is also quite apparent in the nose which has deep oak spice at level that eclipses Old No. 7. Underneath the oak are the signature Jack Daniel’s vanilla, caramel and cola notes as well as a touch of dried orange peel. All these elements come together nicely for a nose that is oaky but inviting.

The entry for Jack Daniel’s Sinatra Select is silky and smooth with a big bold oak flavor that’s initially balanced by the vanilla and caramel from the nose. The oak keeps on building and in the midpalate it overwhelms everything else. It’s here that the oak is joined by clove and a black pepper spice. The finish is long and oaky with the oak, black pepper and clove lingering on the palate for a long time. Adding a little water or ice does help balance things out initially but it also seems to pump up some of the harsher elements in the oak in the midpalate and finish. Unfortunately, using grooved staves is like trying to rush a slow cooker roast, and anything you do to try to accelerate the maturation/cooking process impacts the final product. With Jack Daniel’s Sinatra Select, the grooved staves have introduced too much tannic oak into the mix in too short a period of time. The upside of this is a nice solid oak nose, but the downside is too many harsh oak elements that throw the balance out.

One the plus side Jack Daniel’s Sinatra Select package is stunning, it’s a special one liter bottle which maintains the signature Jack Daniel’s look but adds an orange top hat seal and stopper as well as a thick leaded base. The bottle comes incased in a fabric covered cardboard locker along with a hard bound booklet that takes a look at the relationship between Frank Sinatra and the Jack Daniel’s brand. Behind the booklet is an invitation to the Jack Daniel’s Country Club which was inspired by a crest once worn by Sinatra. Packaging is important, but so is the spirit inside the bottle and it’s hard to get around the fact that Jack Daniel’s Sinatra Select is over oaked.

At $30 or even $40 a bottle, this oaky spirit might be a fine alternative to the other oak forward spirits on the market, like Jim Beam’s Devil’s Cut but Jack Daniel’s has priced this at a staggering $165 per liter (which adjusts out to $123.75 if it were sold in 750ml). Sinatra select is over three times as expensive as Jack Daniel’s Single Barrel which costs $45 a bottle, is higher proof and does a much better job of balancing its oak. While we understand there’s a fair amount of expense in the premium packaging, the pricing here just doesn’t make sense. We are at a complete loss to understand what Brown Forman and Jack Daniel’s were thinking here. It’s one thing to release a series of special select barrels at a premium price, as George Dickel does with their Dickel Barrel Select at $45, but to push process a whiskey with grooved staves and then mix it with standard Old No. 7 at $165 a liter is just madness. We have no problem with high priced ultra premium and rare spirits, but there has to be some sort of case made to justify their price and we just can’t see the price justification with Sinatra Selec t.

How to Mix Frank Sinatra's Favorite Cocktail

Frank Sinatra drank expensive red wines, and mixed martinis for his friends on the set of “Ocean’s Eleven.” And, he never forgot a pal’s favorite drink (according to Sinatra’s old friend Ed McMahon). But his own drink was a simple, but exacting mix of ice, Jack Daniels Tennessee whiskey and water. “This is a gentleman’s drink,” is how he described it. “This is nice.” He called it “The Black Ass of Jack Daniel,” on occasion.

Use a leaded crystal glass, if possible. Sinatra was a fan of elegant glassware, and built a voluminous collection. He believed that good glassware brought out the best in any booze.

Drop four cubes—no more—into the glass. Sinatra would pick out any more cubes than four with a spoon, and admonish the bartender that he wanted to drink, not skate.

Pour two fingers of Jack Daniels over the ice—no more. His bodyguards would tell bartenders “Don’t try to be his friend by mixing it heavy. He don’t like it like that.” Sinatra once described a drink too heavy in whiskey as “Sammy Davis in a glass.”

Fill the remainder of the glass with a quality still water, like Poland Springs. Sinatra drank water only as a cocktail mixer, never for refreshment, or even as a back to a cocktail. “I’m thirsty, I’m not dirty,” he would scowl.

Allow the drink to settle for two minutes. Sinatra would drink martinis right on pouring, but believed that allowing a mixed drink on the rocks allowed it to settle, and brought out its subtleties.

Drink your Black Ass of Jack Daniel Sinatra’s way. He did not hold cocktails by the rim, and infrequently set them down. He would cup them in his hand, insulated by a cocktail napkin.

Keep ice and Jack Daniels nearby Sinatra would refill his cocktail constantly, rather than pour a new one.

Review: Jack Daniel’s Sinatra Century

Jack Daniel’s is making a second stab at Sinatra’s legendary love of JD with another ultra high-end bottling of its signature Tennessee Whiskey. If you thought Sinatra Select was ostentatious, wait’ll you get a load of Sinatra Century, which arrives at more than twice the price.

Sinatra Century — bottled in honor of Frank’s 100th birthday — is made from the same type of alligator-charred barrels as Sinatra Select but otherwise offers no particular production information (including, as usual, any age statement). What JD has done, however, is work with the Sinatra family to taste and select the barrels that went into this bottling.

Bottles are individually numbered and come in elaborate gift packaging. They are bottled at 100 proof, perhaps another nod to the Ol’ Blue Eyes’ centennial.

You have time to consider this purchase — Frank’s birthday will be December 12, 2015 — but in the meantime, let’s give it a thorough tasting and review.

Sinatra Century is immediately appealing from the moment the bottle is cracked open. The nose is heady, with heavy baking spice notes — highly unusual for JD — loads of cinnamon and nutmeg, plus brown butter, some barrel char influence, and ample vanilla. There’s a fair amount of alcoholic burn given the proof, but it’s manageable and actually quite engaging, working well with the grandiose nose.

On the palate, Sinatra Century keeps it going. Big butterscotch, cinnamon, and a healthy slug of Mexican chocolate lead the way. Some charcoal notes make an entry later on, but the finish runs to bittersweet cocoa, a slight cherry influence, and smoldering molasses left on the fire overnight.

The balance of flavors here is nearly perfect, bouncing from spice to chocolate to char and back again. The higher proof helps keep it alive on the tongue for ages, but it never feels particularly hot and doesn’t need water. Engaging from start to finish, I’m not afraid to say this is the best product JD has ever put into a bottle.

That said, it’s a $400 product (or more) — so it better be good. Damn good.

Author David Lehman Takes On Jack Daniel’s Sinatra Century

1. The Background

Frank Sinatra discovered Jack Daniel’s one sleepless night in the early 1940s. “It’s been the oil to my engine ever since,” he later said. He famously praised “anything that gets you through the night, be it prayer, tranquilizers or Jack Daniel’s.” Frank always kept a bottle nearby, offstage, and he was buried with a flask of JD in his casket.

In her autobiography, Judith Campbell Exner —the moll who was mistress to both John F. Kennedy and the head of the Chicago mob—recalled a day spent with Sinatra. He “acknowledged the comings and goings of an endless string of visitors, growled at flunkies, drank martinis, ate lunch, drank Jack Daniel’s, ate hors d’oeuvres, drank Jack Daniel’s, ate dinner, and drank more Jack Daniel’s.”

By the mid-1960s, Sinatra could drink a fifth of Jack Daniel’s and still go on stage.

2. The Anticipation

Like any respectable Sinatra aficionado, I’ve imbibed my share of Tennessee’s trademark sour mash whiskey. And as the author of a new book titled “Sinatra’s Century,” I had extra incentive to try the latest ultra-premium Jack Daniel’s bottle, sent to me by my editor at The Wall Street Journal. Called, by coincidence, Sinatra Century, the limited-edition 100-proof whiskey was aged in 100 “alligator-charred” oak barrels (so called for their scaly interior surface, the deepest of all the chars used to impart flavor and color to the liquor). It hit shelves in October, in plenty of time for toasts to Frank Sinatra on his 100th birthday, December 12, 2015.

I wrote my book because I’ve loved the singer’s voice, musical savvy and definitive versions of standards ever since I heard “All the Way” and “Witchcraft” on the radio when I was 8 or 9. Timing it to the centennial, I wrote the book in 100 parts, because Sinatra’s career ran parallel to and threw into relief what Henry Luce called the “American century,” and because the century is the perfect form for a subject with so many facets.

Jack Daniel’s already has a top-shelf whiskey with Sinatra’s name on it: Sinatra Select, which is selling well at twice the price of single-barrel bourbons that are just as good. Part of me wondered whether, with “Sinatra Century,” JD is selling a name and a future souvenir rather than a whiskey that can go head-to-head with A. H. Hirsch Reserve or the best of Buffalo Trace’s Antique Collection.

3. The Presentation

The packaging of Sinatra Century is as lavish as it should be, priced at $379 or more per one-liter bottle. It arrives in a lacquered case with an engraved brass handle. Pop open the case, and the bottle sits like a dark liquid jewel set against black velvet. Each bottle is numbered—mine is FAS 23095, the initials standing for Francis Albert Sinatra. Also included: a slim hard-bound book devoted to Sinatra’s relationship with Jack Daniel’s and a tie clip that doubles as a thumb drive.

The last item comes loaded with a previously unreleased album of a live Sinatra performance: 13 songs, two monologues and a coda consisting of a brief monologue and foreshortened reprise of “My Kind of Town” as exit music, all recorded at the Sands Hotel in Las Vegas in January 1966. Frank had just turned 50 and was teamed with brilliant arranger Quincy Jones and the Count Basie Orchestra. What better way to return to that evening than with a rocks glass in hand?

4. The Proof

More Message in a Bottle

Isn’t “proof” a lovely word? It stands in one context for the potency of a potable, and in another it means verification: a geometrical proof, say. Both senses come into play here. Would Sinatra Century prove potent enough to accompany belters like “Luck Be a Lady” and “Fly Me to the Moon”? At 100 proof, it had better.

As to color, I said amber, my wife said topaz. She described the taste as “warm orange afterglow.” I sipped again and said, “Cognac.” She said, “The Cognac of bourbons.” Goes well with dark chocolate. Warms the soul “in a drear-nighted December” (to quote Keats). The whiskey is the best I’ve had from Jack Daniel’s.

How to drink it? Neat or over ice. We stuck to Sinatra’s recipe: “three rocks, two fingers and a splash.” We omitted the splash.

5. The Playlist

Sinatra Century promises not merely a whiskey but an experience. So you’re sitting in your favorite reclining armchair sipping and playing the recording of that Sands appearance of January 1966. It opens with a trusty icebreaker, “Come Fly with Me,” then turns to a ballad he’s sung since his crooner days, the Gershwins’ “I’ve Got a Crush on You.” Self-consciousness spoils the verse intro. The skinny singer can scarcely keep a straight face when obliged to sing “I’m your big and brave and handsome Romeo.”

He’s on safer ground with Cole Porter’s “I’ve Got You Under My Skin.” Perhaps the most celebrated of all Sinatra’s up-tempo finger-snappers, it brings out his swinging best. In adapting Nelson Riddle’s 1956 arrangement, Quincy Jones makes miraculous use of reeds and muted horns to compensate for the lack of a string section.

Sinatra always maintained he was at heart a saloon singer and he proves it anew in “Street of Dreams” and Matt Dennis’s great, haunting “Angel Eyes.” As you savor another swallow, the pace changes with “Fly Me to the Moon,” a highlight of the night. Sinatra reinvented Bart Howard’s 1954 song: It wasn’t a sad wistful plea, after all, but an assertive proclamation of love. It was also a nod to NASA’s great decade, the conquest of space as a seduction song. Killer arrangement. Love that flute.

The timeless “You Make Me Feel So Young” shows Sinatra at his most buoyant, and then he turns up the warmth in Johnny Mandel’s Oscar-winning “Shadow of Your Smile.” Sinatra is dating Mia Farrow and Mia likes the song.

Frank Loesser’s “Luck Be a Lady” comes from the musical “Guys and Dolls.” In the movie version, Sinatra played Nathan Detroit, but it was Marlon Brando as Sky Masterson who got to sing this ode to gambling that marks the show’s heroic climax. Now, to correct the injustice, Sinatra demonstrates how the song should be sung. One of Sinatra’s anthems in the 1960s, a hymn to Las Vegas, here it’s as electric as “Fly Me to the Moon,” with a tail like that of “My Kind of Town.”

The audience is hushed when Frank sings “It was a Very Good Year,” where again the reeds do the work of strings, and then the Rodgers and Hart standard “Where or When,” not only a marvelous love song but also the greatest ever on the subject of déjà vu: “Some things that happen for the first time / Seem to be happening again.”

The nightclub act ends with a song Sinatra owns: “My Kind of Town,” the terrific tribute to Chicago that Sammy Cahn and Jimmy Van Heusen wrote for their boss to sing in “Robin and the Seven Hoods,” his last movie musical.

By now you’ve made a dent in the bottle and you’re robustly singing along.

More Message in a Bottle

—Mr. Lehman is the author of “Sinatra’s Century: One Hundred Notes on the Man and His World” (Harper).

Copyright ©2020 Dow Jones & Company, Inc. All Rights Reserved. 87990cbe856818d5eddac44c7b1cdeb8

Watch the video: Jack Daniels Sinatra Select. The Whiskey Dictionary (January 2023).