Challenges in the Life of Frank Sinatra in a Detailed Timeline

A closer look at the defining struggles that shaped Frank Sinatra's life and career.

Frank Sinatra, a highly acclaimed American singer and actor, remains one of the most iconic entertainers of the 20th century. Known by monikers such as "Chairman of the Board" and "Ol' Blue Eyes," Sinatra achieved global fame and sold an estimated 150 million records, establishing himself as one of the best-selling music artists worldwide. His influence on music and popular culture endures.

Sections (6)

Full Timeline Early Life & Education Career & Achievements Success & Recognition Challenges & Struggles Legacy & Impact

1931: Attended and expelled from A. J. Demarest High School

In 1931, Frank Sinatra attended A. J. Demarest High School (now Hoboken High School) but left without graduating after 47 days due to expulsion for "general rowdiness".

August 1942: Legal battle with Dorsey settled

In August 1942, a legal battle between Frank Sinatra and Tommy Dorsey was settled, freeing Sinatra to pursue his solo career but required him to pay Dorsey 43% of Sinatra's lifetime earnings.

December 11, 1943: Classified 4-F

On December 11, 1943, Frank Sinatra was officially classified 4-F by his draft board, making him "not acceptable for military service" due to a perforated eardrum. Army files indicated the real reason was his emotional instability.

1948: Decline in Popularity

By the end of 1948, Frank Sinatra had slipped to fourth on DownBeat's annual poll of most popular singers.

1949: Further Decline and Album Panned

In 1949, Frank Sinatra was pushed out of the top spots in polls for the first time since 1943, and his album Frankly Sentimental was panned by DownBeat.

January 1950: Death of Publicist George Evans

In January 1950, Frank Sinatra's publicist, George Evans, died, which was an enormous shock to Sinatra and crucial to his career and popularity.

1950: Vocal Hemorrhage Comparison

In 1950, Frank Sinatra suffered from a vocal hemorrhage. Stan Cornyn compared Sinatra's soft singing on the Francis Albert Sinatra & Antônio Carlos Jobim album to the time of his vocal hemorrhage.

September 1951: Las Vegas Debut

In September 1951, Frank Sinatra, facing financial difficulties and career decline, made his Las Vegas debut at the Desert Inn.

April 1952: Performance at Kauai County Fair

By April 1952, Frank Sinatra's decline in popularity was evident, leading him to perform at the Kauai County Fair in Hawaii.

September 17, 1952: Last Recording for Columbia

On September 17, 1952, Frank Sinatra's last studio recording for Columbia, "Why Try To Change Me Now", was recorded in New York.

1962: Snubbed by President Kennedy

In 1962, Frank Sinatra was snubbed by President Kennedy, who stayed with Bing Crosby due to FBI concerns.

1963: Suspension of Gambling License

In 1963, Frank Sinatra's gambling license was temporarily suspended after Giancana was spotted at the Cal Neva Lodge & Casino, leading to him giving up his share in Cal Neva and the Sands. His son, Frank Jr., was also kidnapped that year.

1970: Release of Watertown

In 1970, Sinatra released Watertown, a critically acclaimed concept album with music by Bob Gaudio and lyrics by Jake Holmes. Despite critical acclaim, it sold only 30,000 copies and reached a peak chart position of 101.

January 1977: Death of Dolly Sinatra

In January 1977, Frank Sinatra's mother, Dolly, died in a plane crash on the way to see him, causing him to cancel shows and recover in Barbados.

1978: Lawsuit against land developer

In 1978, Frank Sinatra filed a $1 million lawsuit against a land developer for using his name in the "Frank Sinatra Drive Center" in West Los Angeles.

September 21, 1983: Lawsuit against Kitty Kelley

On September 21, 1983, Frank Sinatra filed a $2 million court case against Kitty Kelley for punitive damages, before her unofficial biography, His Way, was even published.

September 19, 1984: Dropped Kitty Kelley Lawsuit

On September 19, 1984, Frank Sinatra was forced to drop the case against Kitty Kelley, with several leading newspapers expressing concerns about censorship.