10 Interesting Facts about Frank Sinatra

Frank Sinatra is one of the most legendary stars of the 20th century, celebrated for his contributions to both music and film. Given how famous he was, it might seem that everything about him is already well-known. Yet, with a career as long as Sinatra’s, countless stories and facts have gone under the radar or have been forgotten with time. In this article, we will shine a spotlight on that forgotten information and look at 10 interesting facts about Frank Sinatra.

1. Frank Sinatra received the most nominations at the first-ever Grammy Awards, but his first win was not for his music

On May 4th, 1959, Frank Sinatra attended the inaugural Grammy Awards as the most-nominated artist of the evening, earning 6 nominations. Among these were nods for ‘Witchcraft’ in the categories of Record of the Year and Best Male Vocal Performance, as well as ‘Only the Lonely’ for Album of the Year, and ‘Come Fly with Me’ for both Album of the Year and Best Male Vocal Performance. Surprisingly, Sinatra’s first Grammy win wasn’t for his music but for his work in art direction; ‘Only the Lonely’ took home the award for Best Album Cover. While it was his sole win that night, Sinatra would go on to secure a remarkable 31 nominations, earning 9 Grammy wins and receiving prestigious honors such as the Lifetime Achievement Award, Trustees Award, and Legend Award.

2. Frank Sinatra won an Oscar for Best Supporting Actor

While Frank Sinatra is best known for his extraordinary singing talent, many forget that he also enjoyed a highly successful acting career. In 1954, he earned an Academy Award for Best Supporting Actor for his portrayal of Private Angelo Maggio in ‘From Here to Eternity.’ The film was a major triumph at the 26th Academy Awards, winning 8 of its 13 nominations, including Best Picture, Best Director, Best Supporting Actor, and Best Supporting Actress. Sinatra’s acting prowess was further recognized the following year when he received a Best Actor nomination for his role in ‘The Man with the Golden Arm.’ However, the award ultimately went to Ernest Borgnine for ‘Marty.’ Spanning from the 1940s to the 1990s, Sinatra’s film career was impressive in its own right, showcasing his versatility and earning him acclaim alongside the most talented actors of his time.

3. Frank Sinatra was one of the first big-name artists to create his own record label

After spending much of the 1950s with Capitol Records, Frank Sinatra parted ways in 1960 following a dispute with Vice President Alan Livingston. Seeking more control over his music, Sinatra initially tried to purchase Verve Records, but when that deal fell through, he established his own label, Reprise Records. Under Sinatra’s leadership, Reprise was founded on the principle of granting artists complete creative control and eventual ownership and publishing rights of their work. The label attracted many acts of the time, such as Bing Crosby, Dean Martin, Sammy Davis Jr., Jimi Hendrix, Duke Ellington, and the Kinks. Although Reprise faced financial struggles, it was acquired by Warner Bros. in 1963, with Sinatra retaining a one-third stake. Today, Reprise remains a prominent Warner Records label. As one of the first major artists to launch his own label, Sinatra set a precedent that may have inspired others, such as Ray Charles, Herb Alpert, and the Beatles, who went on to found labels in the 1960s.

4. Frank Sinatra was an avid collector of model trains

Frank Sinatra developed a love for collecting toy trains in the early 1940s, a hobby he picked up from Tommy Dorsey, the bandleader of the group Sinatra sang with at the time. He had a particular fondness for Lionel model trains, which made up the majority of his collection. At his home in Rancho Mirage, California, Sinatra dedicated an entire building to this passion, housing a collection reportedly valued at over a million dollars. The highlight of the space is an impressive railroad layout, measuring 12 feet (3.66 meters) by 24 feet (7.32 meters), featuring a detailed city scene complete with tunnels, stations, houses, greenery, hills, and mountains.

5. Frank Sinatra has writing credits on only seven songs

Frank Sinatra is a legendary performer known for his extensive catalog of iconic songs. However, many may not realize that most of his recordings were either covers of existing songs or pieces written specifically for him by other songwriters. Sinatra has songwriting credits on only seven tracks, all co-written. These songs are This Love of Mine, Peachtree Street, Take My Love, I’m a Fool to Want You, Sheila, Mistletoe and Holly, and Mr. Success. While none became significant hits for Sinatra, many of the songs achieved moderate success.

6. Sinatra’s ‘Fly Me to the Moon’ was played on the Apollo 11 Moon landing mission

Unsurprisingly, given its lyrics and popularity during the 1960s, Frank Sinatra’s rendition of Fly Me to the Moon became closely associated with NASA’s Apollo space program, serving as an unofficial anthem for the Moon landings. Buzz Aldrin, an Apollo 11 astronaut and the second person to walk on the Moon, shared with Quincy Jones, who arranged Sinatra’s version of Fly Me to the Moon, that during the first manned mission to land on the moon, he listened to the song on a cassette just before stepping out of the spacecraft.

7. Frank Sinatra’s son was kidnapped and held for ransom

On December 8th, 1963, the 19-year-old son of Frank Sinatra, Frank Sinatra Jr., was kidnapped and held for ransom. Amateur criminals Barry Keenan and Joe Amsler abducted the singer from Harrah’s Club Lodge in Lake Tahoe, Nevada, and demanded $240,000 in ransom from his father. Despite the plan’s initial success, Frank Sinatra Jr. was freed unharmed three days later after co-conspirator John Irwin released him out of fear while Keenan and Amsler were picking up the ransom money. The FBI tracked the kidnappers through fingerprints, recovered most of the ransom, and convicted the three men.

8. Sinatra was also a film director

Another interesting fact about Frank Sinatra’s movie career is that he directed a major feature film. In 1965, he directed the World War II drama None But the Brave. The film, in which Sinatra also stars in, follows American and Japanese soldiers stranded on a Pacific island together. The film initially received negative reviews but has since been praised by critics for showing the Second World War from both the US and Japanese sides. As well as being Sinatra’s first (and only) directed film, it also holds the title of being the first major feature film produced jointly by Japan and the United States.

9. Frank Sinatra’s career almost ended in the 1950s

In the early 1950s, Frank Sinatra’s career hit a dramatic low, teetering on the brink of collapse. His 1949 album Frankly Sentimental was poorly received by critics, and his music struggled to gain traction, with ‘The Hucklebuck’ marking his last top-ten hit for years. Adding to his woes, Sinatra faced personal setbacks, including the death of his publicist George Evans, a key figure in his early success, and an affair with Ava Gardner that tarnished his public image. Health issues further derailed his career, forcing him to cancel performances, while financial difficulties led to both Columbia Records and his agent, MCA, dropping him in 1952. Even in Las Vegas, where Sinatra pioneered the concept of residency entertainment, he often performed in half-empty rooms at the Desert Inn. Had it not been for his Oscar-winning performance in the 1953 film From Here to Eternity, which reignited his career, Sinatra may never have had the chance to create many of the iconic hits he is celebrated for today.

10. Frank Sinatra believed “Something” by The Beatles was the greatest love song of the last 100 years

When the Beatles burst onto the American music scene, taking the country by storm, Frank Sinatra was unimpressed. A staunch critic of rock and roll, he viewed the Beatles as the epitome of a genre he never embraced. While promoting his album A Man and His Music, Sinatra said, “If you happen to be tired of kid singers wearing mops of hair thick enough to hide a crate of melons…it should be refreshing.” However, his opinion softened when he encountered George Harrison’s ‘Something,’ featured on the Beatles’ Abbey Road album. The song impressed Sinatra so deeply that he called it “one of the best love songs to be written in 50 or 100 years, and it never says ‘I love you’ in the song.” In October 1970, he recorded his own rendition of the song as a single and made it a staple in his concert performances.

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