Frank Sinatra

Photo of Frank Sinatra
  • Birth Name

    Francis Albert Sinatra
  • Born

    December 12, 1915
    Hoboken, New Jersey
  • Died

    May 14, 1998 (age 82)
    Los Angeles, California
  • Orchestras

    Tommy Dorsey
    Harry James

Perhaps the most important vocalist of the twentieth century, Frank Sinatra is rivaled only by Bing Crosby in his contribution to American popular song. His smooth voice and uncanny sense of rhythm coupled with his tough-guy personality and deep sense of humor won him the adoration of jazz fans and the general public alike. Nicknamed Ol’ Blue Eyes and the Chairman of the Board, he is remembered today more for his classic solo work of the 1950s and 1960s than for his big band days.

A New Jersey native, Sinatra grew up in Hoboken and dropped out of high school to pursue a singing career. As part of the Hoboken Four, he won a contest on the Major Bowes Amateur Hour in 1935 and toured with the show for the next three seasons. In 1937, he was part of the same Bowes unit as future Glenn Miller singer and Modernaires associate Paula Kelly, who was a member of the Kelly Sisters act. After leaving Bowes, Sinatra found work as a singing waiter and Master of Ceremonies at the Rustic Cabin nightclub in Englewood, New Jersey, where he received broadcast time.

The story goes that vocalist Louise Tobin, then wife of bandleader Harry James, heard Sinatra on the radio one night in 1939 and alerted her husband. James liked his voice and hired him for his new orchestra. Sinatra joined the band in June, initially sharing the bandstand with Connie Haines, though Haines was soon let go. A disastrous tour at the end of the year left the group in financial trouble, and James struggled to complete an engagement at Chicago’s Sherman Hotel in January 1940. Tommy Dorsey was in town at the same time, and dissatisfied with his then male vocalist, Allan DeWitt, he offered Sinatra a job. With Sinatra’s wife expecting and the band’s future uncertain, James let him go.

Dorsey Years

As part of Dorsey’s vocal staff, Sinatra reunited with Haines and also worked alongside Jo Stafford and the Pied Pipers. Dorsey’s orchestra was one of the top in the nation at the time, and its high profile put Sinatra in the limelight. He quickly become the band’s star attraction, singing on sixteen Top Ten hits over the next two-and-a-half years, including the classic number one “I’ll Never Smile Again.” He earned first place in Billboard magazine’s 1941 college poll for best male band vocalist and second place in 1942, barely edged out of first by Ray Eberle. He was back in first place for 1943. In Down Beat magazine’s 1939 poll, Sinatra had placed twelfth in the category of male vocalist, this while he was still with James. In the 1940 poll, after a year with Dorsey, Sinatra ranked third, behind Bing Crosby and Ray Eberle. In 1941, he placed first, edging out Bob Eberly. He maintained that position in the 1942 results with a commanding lead over Crosby.

Even during his early days, Sinatra’s well-known personality showed itself. In mid-1940, he beat up Dorsey drummer Buddy Rich, who was bigger than him. The reason for the fight wasn’t given, but Rich’s behavior was often criticized by his bandmates. It wasn’t the only time Rich suffered a beating while with the band.

In early 1941, shortly before a show in Hartford, Connecticut, police arrested Sinatra for jaywalking. An officer yelled at him to stop, but Sinatra kept walking, yelling back “I’m already half across now.” The officer promptly arrested him and took him to jail. Sinatra told police that he was a “figure of national importance” and was due on the stage any minute, to which police replied that he should call another “figure of national importance” down to the station for help. Bobby Burns, Dorsey’s then band manager, soon arrived, and Sinatra was let go after buying a ten dollar ticket to a police benefit. He made the show on time.

Rumors frequently circulated, as early as mid-1941, that Sinatra would leave Dorsey and go solo, but he was cautious in his decision. To test the waters, he recorded four songs under his own name in early 1942 on the Bluebird label, with Axel Stordahl conducting. Encouraging reviews gave him confidence in his chance of success, and Sinatra finally announced his departure in August, giving his last performance with Dorsey on September 10 in Indianapolis. Under the contract Sinatra had signed upon joining the band, he was handled by Dorsey’s personal management office, and Dorsey was thus entitled to a share of his solo earnings, something Sinatra later came to regret.[1] Dick Haymes replaced Sinatra in Dorsey’s band.[2]

The Swoon King

As Sinatra began his solo career, a recording ban instituted by the American Federation of Musicians was in full swing. Though he was unable to record, he continued to tour and to appear on radio, beginning a new CBS sustaining series, Reflections, on the first of October. In late 1942, he filmed his first credited screen role in Columbia’s Reveille with Beverly, singing “Night and Day,” one of the tunes he had recorded solo earlier that year. His defining moment came in January 1943 during a live performance at the Paramount Theater in New York, where he opened for Benny Goodman. Young fans went wild over him. Girls swooned upon hearing his voice, and he was mobbed by adoring fans. RCA Victor and Columbia capitalized on this phenomenon by issuing previously unreleased Dorsey and James vocal recordings which featured Sinatra. Signing with Columbia, he skirted the AFM ban by making several a cappela recordings.

Sinatra quickly became the hottest act in the nation. Touring in 1943, he filled stadiums and parks, breaking box office and attendance records everywhere he went. In mid-1943, he began appearing with symphony and philharmonic orchestras, attracting younger fans than they typically would see and bringing in much-needed revenue for these organizations that often operated at a deficit. When Sinatra played the Hollywood Bowl in late 1943, they installed special “swooning stations” around the facility.

After his Paramount appearance, CBS moved Sinatra to their popular Your Hit Parade show. By mid-year, he was also starring in his own variety program, The Broadway Band Box, with Raymond Scott’s orchestra. In late 1943, he appeared in his first starring role in a Hollywood film. RKO purchased the rights to the play Higher and Higher specifically as a vehicle for Sinatra, but contractual obligations forced them to list two other stars above him.

Though Sinatra was flying high, his financial picture was far from rosy. Due to his contract with Dorsey, the bandleader owned 33⅓ of Sinatra’s earnings, and Sinatra’s manager, Leonard Vannerson, who was also Dorsey’s manager, owned ten percent. In addition, Sinatra’s booking agency, General Amusement Corporation, owned a stake in the singer. Down Beat estimated that Sinatra only owned 46⅔ of himself. Other deals that Sinatra had made prior to his meteoric rise to fame also took chunks out of his paycheck. In mid-1943, Sinatra hired a lawyer and an accountant to help him straighten out his financial obligations. He offered to buy out Dorsey’s interest in him, eventually settling for over $50,000 to pay off all parties involved.[3]

By 1944, Sinatra was commanding a massive $25,000 a week for theater appearances, more than most orchestras. He placed first in Down Beat’s 1943 reader’s poll for best singer with a commanding lead over Bing Crosby. 1944, however, saw the results reversed, with Crosby well ahead of Sinatra. The 1945 results were closer but with Crosby still in the lead, with 1946 again seeing Sinatra well on top.

Later Career

Sinatra charted several hits during the mid-1940s and scored big at the box office, but by the late 1940s his career had stagnated. As the 1950s rolled around, his popularity was in decline. He continued making films and appearing on the radio, though in lesser roles. He also hosted his own television musical-variety program from 1950 to 1952. By the end of 1952, however, he was off the airwaves completely and without a film or recording contract, having left Columbia after a dispute over material.

Aiming to make a comeback, Sinatra tightened his belt and signed a less-than-desired contract with Capitol Records. Soon he was charting hits again. He also took a non-singing role in the motion picture From Here to Eternity and impressed the film establishment so much that he was awarded an Oscar for Best Supporting Actor. He was back on radio as well, in both a dramatic role, as detective Rocky Fortune, and as a singer.

Sinatra continued recording, making films, and appearing on radio and television throughout the 1950s and 1960s. In 1960, he formed his own record label, Reprise, though he still was under contract with Capitol until 1962. He was prolific in the studio, often releasing three albums in one year. By the early 1960s, the market was oversaturated with Sinatra recordings and sales slacked off. The changing tastes of the America music buying public also began to take their toll. Though Sinatra was still a best-seller, he charted less frequently in the late 1960s, finding it hard to compete with modern rock and pop artists. He briefly flirted with the youth market, to some success, but in 1971 gave in and announced his retirement.

Sinatra didn’t stay retired for long, returning to the public eye in 1973 with a gold album and a television special. This time around, though, he prudently decided to focus less on recording and more on live performance. Several years elapsed between album releases. He stayed out of the studio completely from 1984 to 1993 when he released Duets, on which he sang many of his old favorites accompanied by popular modern vocalists. It became his best selling album of all time. In 1994, he followed it up with Duets II.

His health declining in the mid-1990s, Sinatra retired for good in 1995. Frank Sinatra passed away in 1998, age 83, after suffering a heart attack.


  1. Dorsey had the same agreement with other singers he employed, including Jack Leonard, Connie Haines, and the Pied Pipers. ↩︎

  2. Music historians often overstate Sinatra’s departure as a watershed moment that marked the beginning of the decline of the big band era, claiming that he inspired other singers to follow his lead. Sinatra, however, was not the first band vocalist to go solo, and he was not the first to find success on his own. His departure was more a symptom of the decline rather than a cause. ↩︎

  3. Dorsey did not offer to pay Vannerson his ten percent interest, which many believed resulted in Vannerson leaving the bandleader’s employ at the first of September. Vannerson was the husband of singer Martha Tilton. ↩︎


  1. Simon, George T. The Big Bands. 4th ed. New York: Schirmer, 1981.
  2. Walker, Leo. The Wonderful Era of the Great Dance Bands. Garden City, New York: Doubleday, 1972.
  3. McCarthy, Albert. The Dance Band Era. Radnor, Pennsylvania: Chilton, 1971.
  4. “Orchestra Notes.” Billboard 22 Jul. 1939: 10.
  5. “Contest Results: Male Vocalist.” Down Beat 1 Jan. 1940: 13.
  6. “Tom Dorsey Gets Frank Sinatra.” Down Beat 1 Feb. 1940: 5.
  7. “T. and J. Dorsey Doing All Right At Astor, Pennsy.” Billboard 13 Jul. 1940: 21.
  8. “Buddy Rich Gets Face Bashed in.” Down Beat 1 Sep. 1940: 1.
  9. “On the Air: Tommy Dorsey.” Billboard 7 Dec. 1940: 13.
  10. “Final Poll Results: Male Vocalist.” Down Beat 1 Jan. 1941: 13.
  11. “Frank Sinatra Jailed; Nearly Misses Show.” Down Beat 15 Mar. 1941: 5.
  12. “Plenty of Bowes Tyros Hit the Gong Instead of Getting It.” Billboard 23 Aug. 1941: 4.
  13. “Vaudeville Review: Paramount, New York.” Billboard 6 Sep. 1941: 22.
  14. “Talent and Tunes On Music Machines.” Billboard 11 Oct. 1941: 67.
  15. “Sinatra Cuts 4 Discs; May Do a Single.” Down Beat 1 Nov. 1941: 15.
  16. “Poll Tabulations: Male Vocalist.” Down Beat 1 Jan. 1942: 21.
  17. “On the Records.” Billboard 7 Mar. 1942: 21.
  18. “Campus Picks Top Chirps.” Billboard 2 May 1942: 19.
  19. “On the Records.” Billboard 2 May 1942: 72.
  20. “Sinatra Quits TD in Winter.” Down Beat 1 Aug. 1942: 3.
  21. “Latest T.D. Bulletin.” Billboard 15 Aug. 1942: 19.
  22. “Sinatra Leaves TD in Sept; Haymes in.” Down Beat 15 Aug. 1942: 1.
  23. “Frank Sinatra Added to Cast Of Filmusical.” Down Beat 1 Oct. 1942: 19.
  24. “Sinatra Begins His Solo Career.” Down Beat 15 Oct. 1942: 15.
  25. “Picture Tie-Ups for Music Machine Operators.” Billboard 17 Oct. 1942: 69.
  26. “Pastor, Sinatra Fine.” Billboard 7 Nov. 1942: 14.
  27. “10-Week Stageshow On Tap for NY Para.” Billboard 21 Nov. 1942: 20.
  28. “Mosque, Newark Tries 2-a-Day Good Show.” Billboard 28 Nov. 1942: 17.
  29. “Advertisers, Agencies, Stations.” Billboard 12 Dec. 1942: 7.
  30. “Poll Results: Male Vocalist.” Down Beat 1 Jan. 1943: 14.
  31. “Frank Sinatra On Hit Parade.” Down Beat 15 Jan. 1943: 3.
  32. “How Columbia Bagged Sinatra.” Down Beat 1 Jun. 1943: 5.
  33. “Students Select Singers.” Billboard 5 Jun. 1943: 20.
  34. “TD Still Owns Sinatra Third Worth 25 Gees.” Down Beat 15 Jun. 1943: 3.
  35. “Sinatra Moo Still Flowing 'Steen Ways.” Down Beat 1 Jul. 1943: 11.
  36. “Sinatra to Make Film Next Month.” Down Beat 15 Jul. 1943: 3.
  37. “Public Swarms To Swoon With Sinatra in Bowl.” Down Beat 15 Aug. 1943: 3.
  38. “Sinatra Packs the Lewisohn Stadium.” Down Beat 15 Aug. 1943: 3.
  39. “T. Dorsey Loses Vannerson Via Resignation. ” Billboard 11 Sep. 1943: 14.
  40. “1943 Poll Poll Winners: Male Singers.” Down Beat 1 Jan. 1944: 13.
  41. The Billboard 1943 Music Year Book Cincinnati: Billboard, 1944. 139.
  42. “News: Male Singer (Not Band).” Down Beat 1 Jan. 1945: 13.
  43. “Band Poll: Male Singer (Not Band).” Down Beat 1 Jan. 1946: 16.
  44. “1946 Band Poll Winners: Male Singer (Not Band).” Down Beat 1 Jan. 1947: 20.
  45. “Poll Results: Male Singer (Not With Band).” Down Beat 31 Dec. 1947: 12.
  46. “The Columbia Sinatra.” Billboard 20 Nov. 1965: 125.
  47. Williams, Richard. “A very long retirement: Sinatra's bittersweet final years remembered.” The Guardian 12 Dec. 2015: