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His Kind of Town

In honor of Frank Sinatra’s 100th, here’s an in-depth look at the long love affair between Chicago and the Chairman of the Board.

Even a century after his birth, the love affair between Frank Sinatra and the Windy City still remains strong.

In the fall of 1939, Chicago was awash in entertainment. At the Three Deuces—222 North State Street—Billie Holiday sang “Strange Fruit,” her haunting new ballad about lynchings in the South. At Chez Paree, the elegant second-floor Streeterville supper club, the comedian Joe E. Lewis headlined an all-star revue. Over at the Chicago Theatre, between showings of the Bette Davis tearjerker The Old Maid, Betty Grable entertained audiences, four years before she’d inspire war-weary GIs with a brazen backside view of her million-dollar legs.

And inside the Hotel Sherman—located where the James R. Thompson Center looms today—the trumpet player Harry James and his big band were burning up the Panther Room. James had just added a new crooner to his orchestra, a scrawny 23-year-old kid he’d discovered singing and waiting tables in a New Jersey roadhouse. His name was Frank Sinatra, and word had gotten around town that he was pretty good.

So Grable corralled the Chicago reporter James Bacon, and one night, they headed over to the Sherman to check him out. “I’ll never forget, the minute Sinatra started singing, every girl left her partner on the dance floor and crowded around the microphone on the bandstand,” Bacon recalled later. “He was so skinny, the microphone almost obscured him.”

It has often been reported that Sinatra first appeared here four years earlier, as a member of the Hoboken Four, on a tour with other acts from the Major Bowes Amateur Hour radio program, the American Idol of its time. Sinatra himself may have encouraged, and even believed, that version—but it doesn’t hold up. His debut in the Loop at the Sherman on Sept. 9, 1939—the opening of an eight-week stand—was the city’s introduction to Young Blue Eyes. It was the start of the crooner’s 55-year love affair with Chicago, his kind of town.

Sinatra headlined the Chicago Theatre, a longtime favorite, when it reopened in 1986.

A century after his birth in a Hoboken, N.J., tenement on Dec. 12, 1915, Sinatra still holds a place in the imagination of Chicago. And the influence always went both ways. The Chicago Theatre, for instance, would become the setting for some of Sinatra’s greatest triumphs. The posh Chez Paree, on Fairbanks Court at Ontario Street (today an event space called Chez), would always welcome him, even during the lean years of the early 1950s. It was there that Sinatra first connected with the three Fischetti brothers, Al Capone’s cousins and well-placed members of the Chicago Outfit. In 1947, Joe Fischetti would invite Sinatra to tag along on a trip to Cuba, where Sinatra met the exiled mob boss Lucky Luciano—an encounter that landed Sinatra in hot water with a 1951 Senate committee investigating organized crime.

As for Lewis, that 1939 Chez Paree headliner: Sinatra portrayed the acerbic comic in the 1957 film The Joker Is Wild. In an early scene, Sinatra sings the Jimmy Van Heusen–Sammy Cahn song “All the Way.” Written especially for the movie, the song won an Academy Award and provided Sinatra with his longest-charting Billboard single. Music for the opening credits? Fred Fisher’s “Chicago (That Toddlin’ Town).” It became a Sinatra standard, particularly in his favorite city.

And finally, there’s Billie Holiday. In September 1939, Sinatra stopped by the Three Deuces to check out her act at the club’s downstairs venue, the Off Beat Room. (Lady Day tried to return the favor, but when she showed up at the Hotel Sherman, she was turned away; she and Sinatra went out partying instead.) As always, Holiday’s way with a song dazzled Sinatra. In 1958, he’d tell Ebony magazine that Holiday “was and still remains the greatest single musical influence on me.”

After their extended stay at the Hotel Sherman, Harry James and his orchestra headed to California, then made their way back to the Midwest. By late December, they were onstage again in the Windy City, appearing (along with the Andrews Sisters) at the Chicago Theatre between showings of a Tyrone Power flick.

Also in town was the trombonist Tommy Dorsey, the “Sentimental Gentleman of Swing,” whose band was setting attendance records at the Palmer House’s Empire Room. After Chicago’s own Benny Goodman, there was then no bigger name in popular music than Dorsey. Sinatra characterized his orchestra as “the General Motors of the band business”—and Dorsey needed a new singer.

As the story goes, both the James and Dorsey bands appeared on Dec. 20, 1939, at Mayor Ed Kelly’s annual Night of Stars Christmas benefit at the Chicago Stadium (longtime home of the Blackhawks). The next day, Sinatra met with Dorsey in his suite at the Palmer House; he walked out as Dorsey’s new singer. After playing a few more gigs with the James band, he performed with Dorsey’s orchestra for the first time, in Rockford, Jan. 26, 1940. Six days later, they were in Chicago recording two songs—“The Sky Fell Down” and “Too Romantic”—for the first of their 83 records together.

It was with the Dorsey band that Sinatra became Sinatra. He scored his first No. 1 Billboard chart record with “I’ll Never Smile Again,” a recurring ballad in the Sinatra repertoire. By studying Dorsey’s trombone technique, he also picked up the ability to sing a long string of musical phrases seemingly without drawing a breath. By July 1942, when Dorsey, Sinatra and the crew returned to the Chicago Theatre, the pupil had begun to eclipse the master. With much public fanfare, private acrimony and financial feuding, that September Sinatra left the band.

In the following years, when, as The Voice, he became an idol to swooning bobby soxers, Sinatra got back to Chicago from time to time. Burly Chicago cops (always Sinatra’s allies) kept mayhem in check during his weeklong appearance at the Chicago Theatre in May 1946. “A slim little guy with curly hair was the reason for the law,” explained the Chicago Tribune, which ended its report with a sly note of disapproval. “Frank Sinatra is generous with his fans and sings a good many numbers, all of them eliciting wails of approval from the audience. Everyone concerned seems to think it’s good, clean fun.”

Over the next six years, as his career waned, Sinatra returned to Chicago for several benefit shows at the Stadium and the Opera House. In June of 1952, with his voice temporarily diminished and his love life (with Ava Gardner) in turmoil, he played to sparse crowds at Chez Paree. Observing the sad scene, the Tribune found the 36-year-old Sinatra “strangely dated.”

From Here to Eternity solved the slump; the movie earned Sinatra an Oscar for Best Supporting Actor in 1954. He earned another Oscar nomination in 1955 for his role in the film version of The Man with the Golden Arm, based on the Chicago novel by Nelson Algren. In Chicago, he sang “The Star-Spangled Banner”—with “astonishing vigor,” said the Tribune—to open the 1956 Democratic National Convention, held at the International Amphiteatre (at 42nd and Halsted streets). In March 1958, he was ringside at the Stadium as Sugar Ray Robinson reclaimed his middleweight crown by defeating Carmen Basilio in a brutal 15-round bout. Fight fans complained about being shoved around by the cops protecting Sinatra and his entourage.

In 1962, he returned, bringing along Dean Martin and Sammy Davis Jr. The unlikely venue was a fading nightclub called the Villa Venice, near the town of Wheeling, northwest of Chicago. For seven days, with two shows a night, the Rat Pack, in its prime, packed the place. Each of the stars performed numerous songs individually— “Volare,” “Chicago,” “What Kind of Fool Am I”—before concluding with 45 minutes of medleys, solos and ad-libs. (The shows resurfaced in 1999 on a CD titled “The Summit.”)

Meanwhile, in a nearby Quonset hut (at Milwaukee Avenue and River Road), Chicago mob boss Sam Giancana, a Sinatra pal and the secret owner of the Villa Venice, was putting on a show of his own. Shuttle buses transported club patrons to the hut, where an elaborate gambling operation was underway. The Villa Venice took in about $300,000 that week; the Quonset hut took in almost as much before abruptly shutting down. As for the stars, they may have enjoyed a healthy payday—or they may have performed for free as a favor to Giancana.

A year later, Sinatra was back in Chicago—or at least the Hollywood soundstage equivalent—filming Robin and the 7 Hoods, the last of the Rat Pack movies. Sinatra is not at his best; the assassination of his friend President John F. Kennedy, which temporarily shut down production, may have contributed to his onscreen ennui. But the rousing final number makes up for it: Clad in a vest and blazer of Lincoln green, he belted out a new Van Heusen–Cahn collaboration: “My Kind of Town (Chicago Is).”

That song—which he first performed here at a July 1965 show at the Arie Crown Theater in McCormick Place—would replace “Toddlin’ Town” in his repertoire, often serving as the closing number to his Chicago shows. (Rat Packer Peter Lawford claimed the song was a secret shoutout to Giancana.) Following a thunderous ovation to the song’s performance at a May 1975 Stadium gig, Sinatra happily quipped, “I accept the nomination!”

He’d return that September for another Stadium show, this time with Count Basie and Ella Fitzgerald. In a City Hall ceremony, Richard J. Daley, a longtime friend, made him an honorary citizen of Chicago, noting that Sinatra could “participate in future elections in Chicago.” In December, Sinatra turned 60, and he closed out 1975 with another sold-out concert at the Stadium. Ecstatic at his reception, he headed for a private dinner at Four Torches in the Lincoln Park Tower—the building still stands, near the intersection of Armitage Avenue and Clark Street—where he and his pals sang Christmas carols until dawn.

The following spring, Sinatra was back in town, holing up, as always, at the Ambassador East (today the Public Chicago). For the duration of his 18-day stay, a trio of cops stood guard outside his penthouse suite, prompting Chicago Daily News columnist Mike Royko to query whether that was the best use of Chicago’s finest. Especially angered by Royko’s suggestion that he wore a toupee, Sinatra replied with a two-page letter calling the columnist a “pimp” and offering to punch him in the mouth. The letter, of course, found its way into a subsequent “Jerko” column and, following a charitable donation, ended up in the hands of a reader. In 2009, Antiques Roadshow appraised the letter at $15,000.

During the last 30 years of his performing career, if you wanted to see Sinatra in Chicago—presuming you didn’t rub shoulders with him while he held court at the Pump Room or grabbed some ribs at Lincoln Park’s Twin Anchors—you almost invariably had to do it at the Stadium or another large arena. Even when he appeared outdoors at Navy Pier in August 1982 for a ChicagoFest quickie, he drew 50,000 fans. (Though in “lamentable voice,” as the Chicago Sun-Times opined, he picked up $235,000 for the 55-minute set.)

There were a few exceptions. In May 1976, during the Royko contretemps, he did a classy three-night stand at the Sabre Room in Hickory Hills, of all places, endearing himself to the sharp-dressed standing-room-only crowds.

And as always, near and dear to his heart, there was the Chicago Theatre. When, in September 1986, the place reopened after a multi-million dollar makeover, it was perhaps inevitable that the 70-year-old Sinatra would be the first act. Both he and the joint acquitted themselves well. He performed even better when he returned to the venue the following April. “There is no mistaking it,” insisted the Tribune. “Sinatra’s mastery is back. And no one seems more pleased about it than the master himself.”

On a sadder note, the Chicago Theatre witnessed the demise of the Rat Pack. In 1988, the Chairman had convinced Davis and a reluctant Martin to join him for a 29-city Together Again tour. Early in the tour, after three nights in March at the Chicago Theatre—an engagement punctuated by backstage shouting matches—Martin abandoned ship. His PR people blamed it on a kidney problem, but within weeks, he was performing in Vegas. Feeling betrayed, Sinatra never spoke to Martin again, a decision he would tearfully regret following his friend’s death on Christmas Day, 1995.

Sinatra soldiered on, always returning to Chicago. Before appearing at the enormous World Music Theatre in Tinley Park (today it’s the Hollywood Casino Amphitheatre), he explained his motivation to the Trib’s Howard Reich. “I adore the city,” he said, “and do so because it’s a big city with the heart of a small town.”

The melancholy finale came on Oct. 22, 1994, at the United Center, the recently opened replacement for the Stadium. Sinatra, eight weeks shy of his 79th birthday, was showing his age. His memory failing, his voice faltering, he struggled at times through the 13-song set. Nonetheless, there was something grandly Lear-like about the old man’s performance, with its contrapuntal blend of fierce pride and soft-spoken humility. The “glorious” results sparked “an emotional tug only the most jaded detractor could resist,” wrote the Sun-Times critic Lloyd Sachs, who sensed that this was Sinatra’s farewell. “Judging by this show, though, it would be a mistake to count him gone.”

Yet he was. After a handful of other concerts, his final performance, a six-song set, occurred in February 1995 in Palm Springs. His penultimate song? “My Kind of Town (Chicago Is).”

Frank Sinatra died in Los Angeles on May 14, 1998. “May you all live to be 102 years old,” he’d once wished others, “and the last voice you hear be mine.”