Hollywood His Way


By Timothy Knight

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In the scores of posthumous tributes paid to Frank Sinatra after his death in 1998, most focused on his extraordinary reign as “The Voice” of twentieth-century pop music.

But Sinatra was much more than a music icon. He was also one of the most popular movie stars of the 1940s, ’50s, and ’60s — an Academy-Award winning actor with some sixty film credits to his name. He starred in some of the most iconic films of the twentieth century and with some of the biggest names of the day. There were his dancing days with Gene Kelly in Anchors Aweigh and On the Town; his acclaimed dramatic turns in From Here to Eternity and The Manchurian Candidate; and his signature Rat Pack movies such as Ocean’s Eleven.

Sinatra: Hollywood His Way is a complete, film by film exploration of this true Hollywood legend. His screen history is vividly brought to life through illuminating reviews, behind-the-scenes stories, and hundreds of rare color and black-and-white photographs, making this the ultimate guide to the films of Frank Sinatra and an essential in the library of any fan.


To Les Krantz, my longtime mentor and good friend

Frankie and Frankie, a legend in the making in the early 1940s.

IN THE SCORES of posthumous tributes paid Frank Sinatra after his death in 1998, most focused on his extraordinary reign as "TheVoice" of twentieth-century pop music. No other singer had ever transfixed so many for so long, in a decades-spanning career that flourished for nearly sixty years and numbered close to 2,000 recordings.The late Elvis Presley may have been "The King," but for millions of fans around the world, Sinatra occupied a position even more rarefied than pop-star royalty. In their eyes, the high-school dropout from a working class Hoboken, New Jersey family was simply the "Chairman of the Board." But Sinatra was much more than a pop-music icon or Italian-American success story.
He was also a bona-fide movie star, a magnetic actor whom critic David Thomson described as ". . . a noir sound, like saxophones, foghorns, gunfire, and the quiet weeping of women in the background." Yet despite sixty-odd movies, an Academy Award, and five straight years as a top ten box-office draw, Sinatra never quite got his due in the Hollywood pantheon. He is considered a singer first—an actor second.Yet with the possible exception of his idol Bing Crosby, no other singer has ever enjoyed more lasting crossover success on the big screen than Sinatra. Or courted public rejection by tackling challenging, image-busting roles in provocative films. Just try to imagine either Presley or Crosby stepping into Sinatra's role as a would-be presidential assassin in Suddenly (1954). It's doubtful that audiences would buy either of them as the paranoid war veteran holding a family hostage, whereas Sinatra is eerily persuasive in the role. He would push himself even further the following year, when he gave an astonishing, Oscar-nominated performance as a drug addict struggling to kick the habit in The Man with the Golden Arm (1955). While Otto Preminger's film may strike contemporary viewers as a hopelessly dated melodrama, Sinatra's performance holds up beautifully.
Admittedly, Sinatra made his share of duds. (What star hasn't?) And in a few films, he appears to be going through the motions, as if he's too bored by the material to care. But at his very best in films—From Here to Eternity (1953), The Manchurian Candidate (1962), and Pal Joey (1957), to name three—Sinatra brings an electric, jazzy energy to the screen. Whether he's singing and dancing with Gene Kelly in On the Town (1949) or trading wisecracks between martinis with his Rat Pack buddies in Ocean's Eleven (1960), Sinatra has charisma to burn. He effortlessly passes the Hollywood litmus test of true stardom: You can't take your eyes off him.
From fluffy romantic comedies to hard-hitting dramas to nail-biting thrillers, Sinatra covered the genre waterfront during his forty-one-year film career. Sinatra: Hollywood His Way is a celebration of the very best of "Ol' Blue Eyes" on the big screen.
The young Frank Sinatra of MGM days

THE 1940s would see both the zenith and nadir of Frank Sinatra's career. His rise to stardom and subsequent fall from grace seemed to mirror the crooner's own somewhat Jekyll-and-Hyde persona.The success of the newly crowned "Sultan of Swoon" was born of his own ambition, his ability to learn from the right mentors, and that elusive lady luck. From early on, Sinatra knew he would need to attract the attention of the big-band leaders if he was going to attract any recording industry or public attention at all. In 1940, he did just that, signing with the Tommy Dorsey Orchestra. It proved to be a fruitful and fortuitous partnership with Dorsey that lasted, officially, two years.
Sinatra, who never had formal training as a singer or performer and could not read music, studied both Dorsey's musical phrasing and his showmanship, with spectacular results. Bobbysoxers were soon screaming and swooning before Sinatra could even step out from behind the curtains. He poured his soul into every performance and sang with a confidence that belied his relative inexperience. As his popularity skyrocketed, Sinatra became one of the first big-band vocalists to close a live show—and he received more applause than the band.
The Tommy Dorsey Orchestra also provided Sinatra's entrée to Hollywood after Paramount Pictures hired the band to appear in Las Vegas Nights (1941), an admittedly run-of-the-mill musical comedy. Sinatra earned his first, albeit uncredited, screen time as a featured vocalist performing "I'll Never Smile Again" with the singing group the Pied Pipers. He next performed a few songs in the MGM musical Ship Ahoy (1942), a bit of wartime fluff starring Eleanor Powell and Red Skelton.
Between 1940 and 1943, Sinatra was listed as Down Beat magazine's top musical performer, knocking Bing Crosby out of the coveted position. In 1942, Sinatra's appearance at New York's Paramount Theater gave proof of growing "Sinatramania," as fans screamed their adoration and he was deemed the "hottest thing in showbiz." His appeal crossed multiple social and gender lines. As few male performers could, he drew admiration from men as well as women; from adults; tweens; and of course, the growing teen population.
Although Sinatra had married his longtime sweet-heart Nancy Barbato in 1939, he nevertheless indulged in a series of affairs that reportedly embarrassed his wife, the mother of his three children: Nancy, Frank Jr., and Tina. And as his star rose, Sinatra also became increasingly volatile and temperamental. He often fired back at the conservative press, who criticized him for failing to serve in the war (he was classified 4-F) and for his outspoken support of President Franklin Roosevelt. Such hotheaded tendencies led to Sinatra's arrest in 1947, when he punched New York columnist Lee Mortimer for suggesting that the crooner had Mafia ties.
Nor did Sinatra win any friends in Hollywood when he voiced his frustration with the filmmaking process, saying, "Pictures stink." Impatient with doing multiple takes, he often refused to do more than one take for a shot, fearful his performance would lose spontaneity. Ironically, he would find some of his greatest success in a series of three musicals with hoofer Gene Kelly, known for his rigorous and demanding dance rehearsals. Kelly wisely tailored routines to Sinatra's natural grace, if limited athletic ability. Their pairing helped create some of the most memorable and iconic moments in film.
But as Sinatra's popularity declined, due to shifting musical tastes and increasing media criticism, the crooner became desperate to salvage his film career. He took roles in forgettable, critically panned box-office bombs, such as The Kissing Bandit (1948), which only hastened his fall from commercial grace.
The dissolution of Sinatra's marriage, instigated by his affair with Ava Gardner, didn't help matters. The two seemed magnetically drawn by their mutual passion, temper, and neuroses, but she refused to continue the relationship unless he divorced Nancy. By 1951, her wish was granted, and Sinatra and Gardner were finally married.
But by 1951, Sinatra would find himself confronting greater threats to his career. The Red Scare spread and the House Un-American Activities Committee began rounding up suspected communists in Hollywood. Sinatra would find himself having to defend his family's and his own liberal tendencies, though he was never brought before the committee.
By 1952, attendance at his live performances had waned, his days at Columbia Records were numbered, and his agency, MCA, informed him they would no longer represent him.Within little more than a decade, Sinatra, now in his late thirties, found himself a "has-been."
Frank Sinatra sheet music; the crooner would soon turn movie star.
Frank Sinatra was a hit in a trio of films with Gene Kelly in the mid to late '40s. Here they perform in Take Me Out to the Ball Game.

Tim Whelan
Jay Dratler and Ralph Spence Based on the musical by Gladys Hurlbut and Joshua Logan
Principal Cast
Frank Sinatra (as himself), Michèle Morgan (Millie Pico), Jack Haley (Mike O'Brien), Leon Errol (Cyrus Drake), Marcy McGuire (Mickey), Victor Borge (Sir Victor Fitzroy Victor), Mary Wickes (Sandy Brooks), Elisabeth Risdon (Mrs. Georgia Keating), Barbara Hale (Katherine Keating), Mel Tormé (Marty), Paul Hartman (Byngham), Grace Hartman (Hilda), Dooley Wilson (Oscar), Ivy Scott (Mrs. Whiffin)
"GOOD MORNING, my name is Frank Sinatra." With those seven words, Sinatra launched a movie career that would span decades. Higher and Higher wasn't Sinatra's first film; he'd previously done musical cameos in a few others, but this RKO film gave him his first starring role.
Then in his late twenties and rail thin, Sinatra was already America's first teen music idol when RKO signed him to a seven-year contract (later bought out by MGM) and cast him in Higher and Higher at the last minute. He plays the singing, piano-playing neighbor of Cyrus Drake (Leon Errol), a down-and-out millionaire who passes his scullery maid Millie (French star Michèle Morgan) off as his long-lost daughter in hopes of marrying her off into wealth. It takes nearly a half hour of the ninety-minute film for Sinatra to appear—but when he does, he rescues this adaptation of a 1940 Broadway musical from mediocrity.
When RKO executives bought the script to the Broadway show, they somehow neglected to purchase the rights to Higher and Higher's chief selling point: a great score by Richard Rodgers and Lorenz Hart. RKO instead hired Jimmy McHugh and Harold Donaldson to write new songs for Sinatra, which he performs with a show stopping display of his dazzlingly versatile voice: "This is a Lovely Way to Spend an Evening," "The Music Stopped," and "I Couldn't Sleep a Wink Last Night." The last was nominated for an Academy Award, as was Constantin Bakaleinikoff 's score. Though neither won, Higher and Higher had no trouble attracting business. "Wink" and "Evening" went on to become big hits for the crooner, and presumably the film itself was just what war-weary audiences needed—lighthearted escapism.
Sinatra, Mickey (Marcy McGuire), and Marty (Mel Tormé) ham it up at Drake's nightclub.
Sinatra finds himself falling in love with Millie (Michéle Morgan), the scullery maid posing as an heiress.
" To Families and Friends of Men and Women in Our Armed Forces: The picture you have just seen is being shown in combat areas overseas with the compliments of the American Motion Picture Academy."
Onscreen announcement at the end of Higher and Higher
Sinatra and Millie look on while Oscar (Dooley Wilson) plays piano at the Drake Mansion.
Of course, for Sinatra, comparisons with Bing Crosby were inevitable; in fact, a line in the film jokingly makes the connection. Crosby had launched his own Hollywood career playing himself in Paramount's The Big Broadcast (1929), and was scheduled for a cameo in Higher and Higher, though it never materialized. Thirteen years would pass before Sinatra and Crosby finally shared the screen in High Society (1956).
While no one mistook Higher and Higher for great art, most critics saw Sinatra's screen potential, with the possible exception of the curmudgeonly Bosley Crowther of the New York Times. Crowther, who would go on to have a love/hate critic's relationship with Sinatra, sarcastically renamed the film Lower and Lower and said, "Frankie is no Gable or Barrymore and the movie registers as a slapdash setting for the incredibly unctuous renderings of the Voice." But Crowther was in the distinct minority, as critics and filmgoers eagerly welcomed a new singing superstar into the Hollywood fold.
Sinatra is literally on cloud nine at the conclusion of Higher and Higher.

Tim Whelan
Warren Duff and Peter Milne
Based on the play Room Service by Allen Boretz and John Murray
Principal Cast
Frank Sinatra (Glenn Russell), George Murphy (Gordon Miller), Gloria DeHaven (Christine Marlowe), Adolphe Menjou (Wagner), Eugene Pallette (Jenkins), Walter Slezak (Joe Gribble), Wally Brown (Binion)
IN LATER YEARS, Frank Sinatra would accumulate the nicknames "Ol' Blue Eyes" and "Chairman of the Board," sobriquets befitting a world weary, sophisticated star. But just twenty-eight in 1944, he was still the skinny kid from Hoboken, the idol of bobbysoxers. He had three movies under his belt, but he was merely the uncredited singer in Tommy Dorsey's band in the first two, Las Vegas Nights (1941) and Ship Ahoy (1942). In the third, Higher and Higher (1943), he got the chance to try his hand at acting, although playing himself was not much of a stretch. It wasn't until 1944 that Hollywood fully unleashed "The Voice" on the movies with a starring role in the musical comedy, Step Lively. If Sinatra's amiable performance does not fully take advantage of his performing skills as Anchors Aweigh (1945) would the next year, or hint at the emotional depths he would achieve in his Oscar-winning turn in From Here to Eternity (1953), it at least suggests that his talents were not simply limited to a velvet voice and the ability to make women swoon.
Sinatra plays Glenn Russell, a sweetly naïve playwright who is swept into scheming Broadway director Gordon Miller's (George Murphy) chaotic universe. The director and his entire company have set up shop in a chic Manhattan hotel, running up huge bills as they rehearse their new musical in Miller's suite, and keeping one step ahead of Wagner (Adolphe Menjou), the hotel boss who is trying to evict them. Russell mistakenly believes the troupe is putting on his socially conscious play and Miller is anxious to be rid of him. But when he hears Russell sing, he realizes he has found a new star—that is, if he ever gets a chance to mount the show.
The young Frank Sinatra strikes a pose that will become a familiar sight in the coming decades.
Mistaking playwright Glenn Russell for a potential backer, Gordon fetes him with alcohol and a cigar.
" That guy is the greatest discovery of my career. Did you see the women around the room while he was singing? Did you see the expressions on their faces? If that guy was the Pied Piper of Hamelin, there wouldn't be a dame left in town."
Gordon Miller (George Murphy) defining playwright Glenn Russell's (Sinatra) true talent
" I didn't learn. I just sang, I guess."
Russell answering the question, "Where did you learn to sing like that?"
Chorus girls surround bathing beauty Christine (Gloria DeHaven) as she luxuriates in the bubbles.
Gordon Miller (George Murphy), Christine Marlowe (Gloria DeHaven), and the chorus rehearse in Gordon's suite.
This was the second adaptation of Allen Boretz and John Murray's 1937 Broadway smash Room Service. The play was refashioned as a Marx Brothers vehicle in 1938, a marriage of slapstick farce with zany comedians that did not quite gel. Frank S. Nugent, critic for the New York Times observed, "There was nothing subtle in the [play's] writing; slapstick seldom is; but on the stage it had the advantage of seeming possible. The producing trio did the most incredible things, but did them out of desperation. With the Marx Brothers, absurdities seem always to be wooed for their own sake. That's a weakness of the picture." Filmgoers evidently agreed. RKO paid $255,000 for the screen rights. The movie went on to lose more than $300,000.
Anxious to see some return on its investment, the studio sought a foolproof box-office draw for the remake, creating an opportunity for Sinatra. After steadily making a name for himself as a singer, first with Harry James and then with Tommy Dorsey's band, he hit the showbiz stratosphere as a solo act when he opened for Benny Goodman at New York's Paramount Theater during an engagement that began on New Year's Eve 1942. The show transformed Sinatra into a genuine phenomenon: the first teen idol of America. His popularity among the bobbysoxer set promised a built-in audience for Step Lively. At the same time, the musical's screwball humor and romance offered appeal beyond Sinatra's young constituency; it gave the singer the chance to broaden his own fan base. This was a win-win situation for both studio and star.
In addition to providing Sinatra with his first real acting job and giving him his first top billing, there were other firsts involved with the making of Step Lively. Although he would not truly show how well he could move until his three musicals with Gene Kelly—Anchors Aweigh, Take Me Out to the Ball Game (1949), and On the Town (1949)—under the tutelage of Step Lively choreographer Ernst Matray, Sinatra proved himself no slouch as a dancer, holding his own in a cast that included ace hoofer George Murphy. The movie also afforded Sinatra his first screen kiss, a chaste smooch with love interest Gloria DeHaven, an occasion of such importance that Look magazine devoted a lavish, four-page spread to it. More important to Sinatra's future were the contributions of songwriters Sammy Cahn and Jule Styne. The tunesmiths were still in the early days of a partnership that began in 1942, and though this nascent collaboration did not yield any terrifically memorable songs, it signaled the beginning of a fruitful relationship with Sinatra.
" He's got charm and personality and that voice! Ho ho!"
Miller singing Russell's praises
Christine and Glenn share a cab and a smooch.
Upon Step Lively's July 1944 release, Time magazine predicted, "Sinatra's name on the marquee is sufficient to guarantee lipsticky posters on the outside, moaning galleryites within." The movie was indeed a hit with his fans. The critics were mostly indifferent to it, but many had kind words for the star."Step Lively is not a very good dish for Sinatra, although it demonstrates that he has far more performing range and assurance than many might have suspected," wrote Howard Barnes in the New York Herald Tribune. Archer Winston in the New York Post was equally complimentary, declaring, "Sinatra . . . is better than in his previous movie efforts. He looks better, acts better, and sings in the manner that has made him famous. If it were not for the rampant demonstration of his fanatics, there would be little to hold against him."
Glenn and Christine make beautiful music together.
Christine and Glenn's number ends in a big finish.
Christine and Glenn lead the chorus as they trip the light fantastic.
While Gordon looks on, Glenn and Christine celebrate their blooming relationship.
A dissenter was the New York Times' Bosley Crowther. In general, it is a positive review, as he concludes, "The whole film was rigged up to ride [Sinatra]. And it carries his meager weight quite well." However, when Crowther writes, "as the yokel playwright who now can sing (a matter, that is, of opinion)," his disdain for one of the greatest vocal talents of the twentieth century is evident. The fans paid Crowther no mind and Sinatra got the last laugh, as Step Lively was but the first lively step in the singer's rapid rise to full-fledged movie stardom.
A playwright no more, Glenn finds his home in the spotlight and a star is born.

George Sidney
Isobel Lennart
Principal Cast
Frank Sinatra (Clarence Doolittle), Kathryn Grayson (Susan Abbott), Gene Kelly (Joe Brady), José Iturbi (himself), Dean Stockwell (Donald Martin), Pamela Britton (waitress from Brooklyn), Grady Sutton (Bertram Kraler), Sharon McManus (little girl beggar)
FOR ANYONE who hadn't yet noticed the skinny crooner from Hoboken, the "Columbus Day riots" of October 1944 sent a message that was heard around the world. For hoards of excited fans, New York City's Paramount Theater became the center of the universe when Frank Sinatra performed for thousands inside, while tens of thousands outside filled the streets. Hundreds of police officers rushed in, trying to make sense and order out of the chaos inspired by the music idol.
Hollywood rushed in too, with MGM offering Sinatra a multiyear contract, and a chance to make Technicolor movie musicals at the studio that invented the style. In a matter of months, the studio's musical production unit was ready to start work on Sinatra's first big-budget film spectacle, Anchors Aweigh (1945).The studio created a perfect package for Sinatra, with top billing, songs by hit makers Sammy Cahn and Jule Styne, multi-talented co-stars, and a clever storyline that emphasized the tender, sentimental side of Sinatra so familiar to fans of his records and radio performances.
As the meek-mannered Clarence Doolittle, a sailor on leave with a wide-eyed "gee whiz" demeanor, Sinatra plays the innocent in Anchors Aweigh with Gene Kelly as his rakish mentor, Joe Brady, the notorious "Sea Wolfʼʼ reputed to have a girl in every port. When the pair earns four days leave in Los Angeles, Clarence tags along with Joe to learn how it's done, and gets a crash course on the art of the pick-up. Before they can get started, however, they're further waylaid by a young runaway named Donnie (Dean Stockwell), whom they escort home to his guardian aunt, a struggling singer named Susan (Kathryn Grayson) who instantly becomes the object of Clarence's affection.
Clarence and Joe celebrate a four-day shore leave with a song.
Long before his fame as an adult, Dean Stockwell played a young wannabe sailor opposite Sinatra in Anchors Aweigh.
" Let me see a sample of your technique. You're you, see, and I'm a dame coming down the street. Pick me up."
Joe Brady to Clarence Doolittle
" I've been in the Navy a year and a half now. Every time we hit port and get liberty, all I do is go to the library."
Clarence Doolittle (Sinatra) to Joseph Brady (Gene Kelly)
Sinatra put in months of intense training to perfect his dance routines with Gene Kelly in Anchors Aweigh. Kelly choreographed all of the film's dance sequences.
Although Joe considers "Aunt Susie" to be a waste of time, he's soon embroiled in an elaborate scheme to secure her an audition with the famous motion picture music director José Iturbi (as himself); once Joe hears her sing, he's instantly smitten with her. Just as suddenly, Clarence realizes that the real love of his life is not Susan but a waitress he calls "Brooklyn" (Pamela Britton), whose East Coast accent, to Clarence's delight, is even thicker than his. Before the romances can be realigned, there are plenty of opportunities for song and dance, including Sinatra's sublime versions of "I Fall in Love Too Easily" and "What Makes the Sun Set?"; the sailors' duet "We Hate to Leave"; and the many astounding Kelly-Sinatra dance sequences in which the world's greatest singer tries to keep up with the world's greatest dancer—and mostly succeeds. The musical numbers stand on their own, which is fortunate since they often have little or nothing to do with the central story. Case in point: the iconic number pairing Kelly with the cartoon mouse Jerry of Tom and Jerry.
Clarence listens in as Joe lines up a date for shore leave.
" I didn't save your life to hand it over to that character. I'm gonna get you a dame that's a dame."
Joe Brady to Clarence Doolittle


  • Library Journal, Oct 2010
    "This highly enjoyable, well-written treat belongs in any library and in the hands of all fans of Frank Sinatra."

    Connecticut Post, 10/21/10
    …a beautiful, oversized volume “Sinatra: Hollywood His Way” that charts the amazing highs and devastating lows of the performer’s 39-year movie career… a wonderful photographic scrapbook of the singer-actor’s entire output, with smart text by Knight.

American Profile, November 2010
“…offers an engrossing, entertaining, photo-packed tribute to his 41 years as a movie star.”

Buffalo News, 11/28/10
“a lavish coffee-table book”

On Sale
Oct 12, 2010
Page Count
336 pages
Running Press

Timothy Knight

About the Author

Timothy Knight is a film critic, scriptwriter, and contributor to many publications and websites about movies. He has written/collaborated on books such as Great Kisses and Famous Lines Right Out of the Movies. He also co-wrote the documentary Their First Time in the Movies. Timothy lives in Los Angeles.

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