Rise to Success: Career Highlights of Frank Sinatra

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Frank Sinatra

From career breakthroughs to professional milestones, explore how Frank Sinatra made an impact.

Frank Sinatra, nicknamed "Chairman of the Board" and "Ol' Blue Eyes", was a highly popular American singer and actor of the 20th century. He is one of the best-selling music artists globally, with estimated record sales of 150 million. Sinatra's widespread appeal cemented his place as a significant figure in entertainment history.

1935: Joined the 3 Flashes

In 1935, Sinatra got his first break by joining a local singing group called the 3 Flashes.

1938: Singing Waiter at The Rustic Cabin

In 1938, Sinatra found employment as a singing waiter at "The Rustic Cabin" in Englewood Cliffs, New Jersey.

March 1939: Recorded First Solo Studio Recording

In March 1939, Sinatra recorded "Our Love", his first solo studio recording.

June 1939: Joined Harry James Big Band

In June 1939, Sinatra joined the Harry James big band as a vocalist, marking an early step in his professional career.

August 1939: Columbia Re-released All or Nothing at All

Columbia Records re-released Harry James and Sinatra's August 1939 version of "All or Nothing at All", which reached number 2.

November 1939: Left Harry James Band for Tommy Dorsey Band

In November 1939, Sinatra left the Harry James band to become the lead singer for the Tommy Dorsey band.

January 26, 1940: First Public Appearance with Tommy Dorsey

On January 26, 1940, Sinatra made his first public appearance with the Tommy Dorsey band at the Coronado Theatre in Rockford, Illinois.

April 1940: First Vocal Hit

In late April 1940, Sinatra's first vocal hit was the song "Polka Dots and Moonbeams."

May 1941: Topped Male Singer Polls

By May 1941, Sinatra topped the male singer polls in Billboard and DownBeat magazines, signaling his rising popularity.

1941: Recorded songs with Tommy Dorsey

In 1941, Sinatra recorded "Oh! Look at Me Now", "Dolores", "Everything Happens to Me", and "This Love of Mine" with Tommy Dorsey.

January 19, 1942: Solo Recordings

On January 19, 1942, Sinatra recorded solo songs including "Night and Day" and "The Song is You", marking a turning point in his career.

August 1942: Legal Battle Settled

In August 1942, Sinatra's legal battle with Tommy Dorsey was settled, paving the way for his solo career.

September 3, 1942: Farewell from Tommy Dorsey

On September 3, 1942, Tommy Dorsey bade farewell to Sinatra as he left to pursue a solo career.

December 30, 1942: Paramount Theatre Opening

On December 30, 1942, Sinatra's "legendary opening" at the Paramount Theatre in New York led to the phenomenon known as "Sinatramania."

1942: Recorded songs with Tommy Dorsey

In 1942, Sinatra recorded "Just as Though You Were There", "Take Me", and "There Are Such Things" with Tommy Dorsey.

February 1943: Performed on Your Hit Parade

From February 1943, Sinatra performed on the radio on Your Hit Parade.

June 1, 1943: Signed with Columbia Records as Solo Artist

On June 1, 1943, Sinatra signed with Columbia Records as a solo artist during the musicians' strike.

1943: First Appearance in Top Spots in Polls

In 1943, Frank Sinatra began his streak in top spots in polls for the first time.

1943: First Solo Nightclub Appearance and Concert Success

In 1943, Sinatra made his first solo nightclub appearance at New York's Riobamba and had a successful concert at the Waldorf-Astoria, securing his popularity.

1943: Recorded songs with Tommy Dorsey

In 1943, Sinatra recorded "It Started All Over Again", "In the Blue of Evening", and "It's Always You" with Tommy Dorsey.

1943: Signed with Columbia Records

In 1943, Sinatra signed with Columbia Records as a solo artist, which led to widespread recognition and fame.

December 1944: End of Your Hit Parade

In December 1944, Sinatra's run on Your Hit Parade came to an end.

1944: Campaigning for Franklin D. Roosevelt

In 1944, Frank Sinatra heavily campaigned for the Democratic Party after meeting President Franklin D. Roosevelt.

1944: Sinatra Releases Music and Performs for Troops

In 1944, Frank Sinatra released "I Couldn't Sleep a Wink Last Night" and recorded "White Christmas." He also entertained troops overseas with the USO and worked with the Andrews Sisters on the radio.

1945: Sinatra's Busy Year

In 1945, despite being heavily involved in political activity, Frank Sinatra sang on 160 radio shows, recorded 36 times, and shot four films, marking a very busy and productive year.

1946: Sinatra's Continued Success

In 1946, Frank Sinatra continued his success by singing on 160 radio shows, recording 36 times, and shooting four films, performing on stage up to 45 times a week, singing up to 100 songs daily.

1946: Sinatra Conducts and Releases Music

In 1946, Frank Sinatra released "Frank Sinatra Conducts the Music of Alec Wilder" and the single "Mam'selle", showcasing his conducting ambitions and musical talent.

1946: Sinatra Releases Debut Album

In 1946, Frank Sinatra released several singles and his debut album, "The Voice of Frank Sinatra", which reached No. 1 on the Billboard chart, selling 10 million records a year.

1946: Debut Album Release

In 1946, Sinatra released his debut album, "The Voice of Frank Sinatra", further solidifying his solo career.

1948: Sinatra's Popularity Slips

By the end of 1948, Frank Sinatra's popularity began to decline, slipping to fourth on DownBeat's annual poll of most popular singers.

1948: Campaigning for Harry S. Truman

In 1948, Frank Sinatra actively campaigned for President Harry S. Truman during the presidential election.

1948: Sinatra Releases Christmas Album

In 1948, Frank Sinatra's third album, "Christmas Songs by Sinatra", was originally released. Due to press negativity surrounding his alleged Mafia connections, Sinatra announced he would donate his wages from the film "The Miracle of the Bells" to the Catholic Church.

1949: Poll Decline and Album Criticism in 1949

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

1949: Appeared in 'On the Town'

In 1949, Sinatra appeared in the musical film "On the Town".

1950: The Frank Sinatra Show Began

In 1950, "The Frank Sinatra Show" began on CBS, marking his presence on television.

1950: Last Columbia Albums Released

In 1950, Frank Sinatra's last two albums with Columbia, "Dedicated to You" and "Sing and Dance with Frank Sinatra", were released, marking the end of his tenure with the label.

September 1951: Sinatra Debuts in Las Vegas

In September 1951, facing financial difficulties and career decline, Frank Sinatra debuted at the Desert Inn in Las Vegas, marking a turning point in his career.

January 1952: Recording of "If I Could Write a Book"

In January 1952, Frank Sinatra recorded "If I Could Write a Book," a song that Granata sees as a "turning point", forecasting his later work with its sensitivity.

April 1952: Sinatra Performs at Kauai County Fair

In April 1952, Frank Sinatra's declining popularity was evident as he performed at the Kauai County Fair in Hawaii, signifying a low point in his career.

September 17, 1952: Last Columbia Recording

On September 17, 1952, Frank Sinatra recorded his last studio recording for Columbia, "Why Try To Change Me Now", marking the end of his relationship with the record label.

1952: Campaigning for Adlai Stevenson

In 1952, Frank Sinatra actively campaigned for Adlai Stevenson during the presidential election.

March 13, 1953: Sinatra Signs with Capitol Records

On March 13, 1953, Frank Sinatra signed a seven-year recording contract with Capitol Records and recorded his first Capitol single, "I'm Walking Behind You".

August 1953: Release of "From Here to Eternity"

The release of the film "From Here to Eternity" in August 1953 marked the beginning of a remarkable career revival for Frank Sinatra, leading to a frenetic schedule of recordings, movies, and concerts.

October 4, 1953: First Performance at the Sands Hotel and Casino

On October 4, 1953, Frank Sinatra made his first performance at the Sands Hotel and Casino in Las Vegas, invited by manager Jack Entratter, marking a significant step in his Las Vegas career.

November 1953: Musical Collaboration with Riddle

In November 1953, Frank Sinatra and Riddle continued their musical collaboration, developing and refining their partnership with Sinatra providing specific guidance on the arrangements.

1953: Won Academy Award for Best Supporting Actor

In 1953, Sinatra won the Academy Award for Best Supporting Actor for his role in "From Here to Eternity".

January 4, 1954: Release of Songs for Young Lovers

On January 4, 1954, Frank Sinatra's first album for Capitol, "Songs for Young Lovers", was released, featuring songs that would become staples of his later concerts.

1955: Release of In the Wee Small Hours and Australian Tour

In 1955, Frank Sinatra released "In the Wee Small Hours", his first 12" LP and concept album, and embarked on his first tour of Australia, marking significant milestones in his career.

1955: Released 'In the Wee Small Hours'

In 1955, Sinatra released the album "In the Wee Small Hours" with Capitol Records, featuring arrangements by Nelson Riddle.

1955: Starred in 'The Man with the Golden Arm'

In 1955, Sinatra starred in the film "The Man with the Golden Arm", showcasing his acting talent.

February 1956: Inauguration of Capitol Records Building Studios

In February 1956, Frank Sinatra's recording sessions inaugurated the studios at the Capitol Records Building, where he recorded songs with a 56-piece symphonic orchestra, showcasing powerful sexual overtones in his vocal performances.

March 1956: Release of Songs for Swingin' Lovers!

In March 1956, Frank Sinatra released "Songs for Swingin' Lovers!", considered one of his best albums, featuring a recording of "I've Got You Under My Skin" which took 22 takes to perfect.

1956: Campaigning for Adlai Stevenson

In 1956, Frank Sinatra actively campaigned for Adlai Stevenson during the presidential election.

1956: Sinatra Conducts, Performs Politically and with The Dorseys

In 1956, Frank Sinatra released "Frank Sinatra Conducts Tone Poems of Color", sang at the Democratic National Convention, and performed with The Dorsey Brothers for a week at the Paramount Theatre, showcasing his diverse talents and activities.

1956: Appeared in 'High Society'

In 1956, Sinatra appeared in the musical "High Society".

1956: Released 'Songs for Swingin' Lovers!'

In 1956, Sinatra released the album "Songs for Swingin' Lovers!" with Capitol Records, featuring arrangements by Nelson Riddle.

June 9, 1957: Sinatra '57 in Concert

On June 9, 1957, Frank Sinatra performed in a 62-minute concert conducted by Riddle at the Seattle Civic Auditorium, marking his first appearance in Seattle since 1945.

1957: Releases of Close to You, A Swingin' Affair!, and Where Are You?

In 1957, Frank Sinatra released "Close to You", "A Swingin' Affair!", and "Where Are You?", his first stereo album, solidifying his image as a swinger and showcasing his musical range.

1957: Won Golden Globe for 'Pal Joey'

In 1957, Sinatra won a Golden Globe Award for his role in "Pal Joey".

1958: Recording Angel Eyes

In 1958, Frank Sinatra recorded Angel Eyes on the Only the Lonely album.

1958: Releases of Come Fly with Me and Frank Sinatra Sings for Only the Lonely

In 1958, Frank Sinatra released the concept album "Come Fly with Me", which reached the top of the Billboard chart, and "Frank Sinatra Sings for Only the Lonely", a collection of saloon songs and ballads, both proving to be commercial successes.

September 19, 1959: Master of Ceremonies for Nikita Khrushchev

On September 19, 1959, Frank Sinatra was the master of ceremonies at a luncheon attended by Soviet Premier Nikita Khrushchev, showcasing his prominence in Hollywood.

1959: Release of Come Dance with Me!

In 1959, Frank Sinatra released "Come Dance with Me!", a highly successful and critically acclaimed album that stayed on Billboard's Pop album chart for 140 weeks and won multiple Grammy Awards.

October 1960: Nice 'n' Easy Tops Billboard Chart

In October 1960, Frank Sinatra's "Nice 'n' Easy", a collection of ballads, topped the Billboard chart and remained in the charts for 86 weeks, winning critical plaudits.

1960: Started Reprise Records

In 1960, Sinatra left Capitol Records to start his own record label, Reprise Records, marking a new phase in his career.

January 1961: Organizing Inaugural Gala for John F. Kennedy

In January 1961, Frank Sinatra and Peter Lawford organized the Inaugural Gala in Washington, D.C. for President John F. Kennedy.

January 27, 1961: Benefit Show for Martin Luther King Jr.

On January 27, 1961, Frank Sinatra played a benefit show at Carnegie Hall for Martin Luther King Jr.

February 1961: Release of Ring-a-Ding-Ding!

In February 1961, Frank Sinatra's album Ring-a-Ding-Ding! was released and became a major success, peaking at No.4 on Billboard. That same month, Reprise Records released albums by Ben Webster, Sammy Davis Jr., Mavis Rivers, and Joe E. Lewis.

1961: Sinatra's Swingin' Session!!!

In 1961, Frank Sinatra featured songs from his 1950 album 'Sing and Dance with Frank Sinatra' on his Capitol release 'Sinatra's Swingin' Session!!!'.

1961: Performances for Mexican Charities

In 1961, Frank Sinatra traveled to Mexico to perform for Mexican charities, marking his early involvement in philanthropic endeavors.

1962: Performances for Mexican Charities

In 1962, Frank Sinatra continued his philanthropic work by traveling to Mexico to perform for Mexican charities.

1962: Concerts in Israel

In 1962, Frank Sinatra gave a series of concerts in Israel.

1962: Collaboration with Count Basie and Conducting Instrumental Album

In 1962, Sinatra collaborated with Count Basie for the album Sinatra-Basie, which was a popular and successful release. Also in 1962, Sinatra released his third instrumental album Frank Sinatra Conducts Music from Pictures and Plays.

1962: Collaboration with Count Basie

In 1962, Sinatra collaborated with Count Basie on the album "Sinatra-Basie: An Historic Musical First."

1962: Release of Sinatra and Strings

In 1962, Sinatra released Sinatra and Strings, a collection of ballads arranged by Don Costa, which became a critically acclaimed work of Sinatra's Reprise period. The album featured a large orchestra, marking a new era in pop music with a lush string sound.

1962: Starred in 'The Manchurian Candidate'

In 1962, Sinatra starred in "The Manchurian Candidate", further establishing his film career.

1963: King at Sinatra's Concert

In 1963, Martin Luther King Jr. sat weeping in the audience at one of Frank Sinatra's concerts as Sinatra sang "Ol' Man River".

1963: Release of The Concert Sinatra

In 1963, Sinatra reunited with Nelson Riddle for The Concert Sinatra, an ambitious album featuring a 73-piece symphony orchestra. The recording took place on a motion picture scoring soundstage with advanced synchronized recording machines.

July 1964: Dedication of the Frank Sinatra International Youth Center

In July 1964, Frank Sinatra attended the dedication of the Frank Sinatra International Youth Center for Arab and Jewish children in Nazareth, demonstrating his commitment to charitable causes.

1964: Released 'It Might as Well Be Swing'

In 1964, Sinatra and Count Basie released "It Might as Well Be Swing," continuing their collaborative work.

June 1965: Charity Performance with Sammy Davis Jr. and Dean Martin

In June 1965, Frank Sinatra, along with Sammy Davis Jr. and Dean Martin, performed live in St. Louis to benefit Dismas House, a prisoner rehabilitation and training center.

September 1965: Release of September of My Years

In September 1965, Sinatra released the album September of My Years, which later won the Grammy Award for best album of the year.

1965: Performance at Newport Jazz Festival

In 1965, Sinatra and Count Basie appeared together at the Newport Jazz Festival, solidifying their frequent collaboration.

1965: Released 'September of My Years' and Emmy Win

In 1965, Sinatra released the album "September of My Years" and starred in the Emmy-winning TV special "Frank Sinatra: A Man and His Music."

February 1966: Recording Sinatra at the Sands

During January and February 1966, Sinatra's first live album, Sinatra at the Sands, was recorded at the Sands Hotel and Casino in Las Vegas, backed by the Count Basie Orchestra and conducted by Quincy Jones.

1966: Donating Fee for Cameo Role

In 1966, Frank Sinatra donated his entire $50,000 fee for appearing in a cameo role in Cast a Giant Shadow to the Youth Center in Jerusalem.

1966: Released 'Sinatra at the Sands' and Collaboration with Tom Jobim

In early 1966, Sinatra released "Sinatra at the Sands" and recorded "Francis Albert Sinatra & Antonio Carlos Jobim" with Tom Jobim.

1967: Recording Sessions with Antônio Carlos Jobim

In 1967, Sinatra had a series of recording sessions with Antônio Carlos Jobim, resulting in the Grammy-nominated album Francis Albert Sinatra & Antônio Carlos Jobim, one of the best-selling albums of the year.

1967: Starred in 'Tony Rome'

In 1967, Sinatra played the title character in "Tony Rome", frequently playing detective roles toward the end of his career.

1968: Working with Hubert H. Humphrey

In 1968, Frank Sinatra worked with Hubert H. Humphrey and remained a supporter of the Democratic Party.

1968: Collaboration with Duke Ellington

In 1968, Sinatra collaborated with Duke Ellington on "Francis A. & Edward K.".

1968: Recording of "My Way"

In 1968, just after Christmas, Frank Sinatra recorded "My Way" in one take, a song written by Paul Anka using the melody of the French song "Comme d'habitude".

April 1969: "My Way" Enters UK Charts

In April 1969, "My Way" entered the UK charts, beginning a long run that included 75 non-consecutive weeks in the Top 40.

1969: Recording Works by Contemporary Artists

In 1969, Frank Sinatra recorded works by Paul Simon("Mrs. Robinson"), the Beatles ("Yesterday"), and Joni Mitchell ("Both Sides, Now") in an effort to maintain his commercial viability.

November 2, 1970: Last Recording Session Before Retirement

On November 2, 1970, Frank Sinatra recorded the last songs for Reprise Records before his self-imposed retirement. The following June, he announced his retirement at a concert in Hollywood.

1970: Shift in Political Affiliations and Racial Issues

In 1970, Frank Sinatra changed his political affiliations and became less outspoken on racial issues, despite his past civil rights contributions.

1970: Endorsing Ronald Reagan

In 1970, Frank Sinatra endorsed Republican Ronald Reagan for a second term as Governor of California, though still a registered Democrat.

1970: Release of Watertown

In 1970, Sinatra released Watertown, a critically acclaimed concept album. However, it sold a mere 30,000 copies that year and reached a peak chart position of 101.

September 1971: "My Way" UK Chart Success

By September 1971, "My Way" remained a hit in the UK charts for 122 weeks, including 75 non-consecutive weeks in the Top 40.

1971: Received Cecil B. DeMille Award

In 1971, Sinatra received the Golden Globe Cecil B. DeMille Award, recognizing his contributions to the entertainment industry.

1971: Sinatra & Company Release

In 1971, Sinatra recorded Denver's "Leaving on a Jet Plane" and "My Sweet Lady" for Sinatra & Company.

1971: Sinatra's Retirement

In 1971, Sinatra retired following the release of "My Way."

July 1972: Supporting Richard Nixon

In July 1972, Frank Sinatra officially changed his allegiance and supported Richard Nixon for re-election in the 1972 presidential election.

November 1, 1972: Raising Funds for Israel and Receiving Medallion of Valor

On November 1, 1972, Frank Sinatra raised $6.5 million in bond pledges for Israel and was given the Medallion of Valor for his efforts.

1973: Comeback with Television Special and Album

In 1973, Sinatra came out of his short-lived retirement with a television special and album, Ol' Blue Eyes Is Back. The album was a success, reaching number 13 on Billboard and number 12 in the UK.

January 1974: Return to Caesars Palace

In January 1974, Frank Sinatra returned to Caesars Palace following his comeback, marking a significant return to live performances.

October 1974: Performance at Madison Square Garden

In October 1974, Sinatra performed at New York City's Madison Square Garden in a televised concert, which was later released as an album titled The Main Event – Live.

1975: Concerts with Count Basie, Ella Fitzgerald, and Sarah Vaughan

In 1975, Sinatra performed in concerts in New York with Count Basie and Ella Fitzgerald, and at the London Palladium with Basie and Sarah Vaughan, giving 140 performances in 105 days.

1979: Grammy Trustees Award and International Man of the Year Award

In 1979, Sinatra was awarded the Grammy Trustees Award and the International Man of the Year Award, celebrating 40 years in show business and his 64th birthday. He also performed in front of the Egyptian pyramids for Anwar Sadat.

1980: Supporting Ronald Reagan in Presidential Election

In 1980, Frank Sinatra supported Ronald Reagan in the presidential election and donated $4 million to Reagan's campaign.

1980: Released 'New York, New York'

In 1980, Sinatra released "New York, New York", a signature song in his later career.

1980: Release of Trilogy: Past Present Future

In 1980, Sinatra's first album in six years, Trilogy: Past Present Future, was released. It was a highly ambitious triple album that garnered six Grammy nominations.

June 1984: Performing at the White House State Dinner

In June 1984, Frank Sinatra performed at the State Dinner in the White House honoring Sri Lankan President J. R. Jayawardena at the invitation of US President Ronald Reagan.

January 1985: Reconciliation with Nelson Riddle

In January 1985, Sinatra and Nelson Riddle reconciled at a dinner organized for Ronald Reagan, where Sinatra asked Riddle to make another album with him.

Mentioned in this timeline

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