You know that Frank Sinatra was as talented a singer as he was an actor. That he had a collection of nicknames, from The Voice to Ol’ Blue Eyes. And that he liked to do things “My Way.” Here are 35 things you might not have known about the legendary crooner.
1. Frank Sinatra’s birth was a traumatic one.
Born on December 12, 1915, in an apartment in Hoboken, New Jersey, Francis Albert Sinatra was blue and not breathing when he was yanked out of his mother with forceps. Thought to be dead, the infant was laid on the kitchen counter while the doctor attended to his mother. His grandmother picked up the newborn, stuck him under some cold water, and little Frank wailed out his first song.
2. Those forceps caused some damage.
Those forceps left their mark on the left side of Sinatra’s face, in the shape of a scar that ran from the corner of his mouth to his jaw line and a cauliflower ear. As a teenager, he was nicknamed “Scarface.” He also suffered a bad case of adolescent acne, which left his cheeks pitted. Self-conscious about his looks as an adult, Sinatra often applied makeup to hide the scars. Even with that, he hated to be photographed on his left side. The physical insecurities didn’t end there: Sinatra also wore elevator shoes to boost his five-foot-seven stature.
3. Frank Sinatra was a rather large baby.
The future crooner weighed a whopping 13.5 pounds.
4. Frank Sinatra carried his own P.A. system.
When Sinatra was just starting out as a singer, he came prepared: he carried his own P.A. system to the dives in which he typically performed.
5. Frank Sinatra’s bad boy image was real.
Sinatra’s bad boy image began with his infamous 1938 mug shot. The charge? The most Frank reason possible: “seduction.” The charge was reduced to “adultery,” then later dropped.
6. Frank Sinatra was one of America’s first teen idols.
In the 1940s, Frank—or Frankie, as he was then known—became one of America’s first teen idols. “The sound that greeted me was absolutely deafening,” Sinatra later recalled of a series of shows he performed in 1942 at New York City’s Paramount Theater. “I was scared stiff. I couldn’t move a muscle.”
7. Some of Frank Sinatra’s screaming fans were paid to be screaming fans.
Not to take anything away from his amazing voice and his ability to excite the female throngs, but the bobbysoxer craze Sinatra incited (so called because the coed fans wore Catholic school-style bobby socks, rolled down to their ankles) had a little help. George Evans, Sinatra’s publicist, auditioned girls for how loud they could scream, then paid them five bucks and placed them strategically in the audience to help whip up excitement.
8. A short film got Frank Sinatra tagged as a Communist sympathizer.
In 1945, Sinatra made a short film, The House I Live In, that spoke out against anti-Semitism and racial intolerance. Ironically, a decade later, its liberal slant got him tagged as a Communist sympathizer during the McCarthy trials. (Sinatra never testified.)
9. The FBI had a file on Frank Sinatra.
Sinatra’s FBI file had been started by J. Edgar Hoover after a radio listener wrote to the Bureau, saying, “The other day I turned on a Frank Sinatra program and I thought how easy it would be for certain-minded manufacturers to create another Hitler here in America through the influence of mass hysteria.” Sinatra had also been investigated by the FBI for reportedly paying doctors $40,000 to declare him unfit to serve in the armed services.
10. Frank Sinatra helped introduce the concept album and box set.
In 1946, Sinatra’s debut release, The Voice of Frank Sinatra, helped introduce both the concept album and the box set. At a time when long-playing records were still novel, Sinatra issued a set of 78 rpm records with eight songs, all with a theme of lost love. It sold for a hefty $2.50 (the equivalent of about $30 today). But the price didn’t prevent it from topping the charts for seven weeks. Two years later, it became one of the first-ever pop music vinyl 10″ LPs.
11. Frank Sinatra attempted suicide several times.
Sinatra’s star fell hard in the early 1950s. He was so low that he even attempted suicide. Walking through Times Square, he saw mobs of girls waiting to get into a concert by new singing sensation Eddie Fisher. Feeling washed up, Sinatra went back to his apartment, put his head on the stove, and turned on the gas. Luckily, his manager found him in time, lying on the floor, sobbing. Sinatra made three other suicide attempts, all of them in the throes of his volatile relationship with actress Ava Gardner.
12. The Rat Pack didn’t call themselves that.
With his pals Dean Martin, Sammy Davis, Jr., Joey Bishop, and Peter Lawford, Sinatra led the Vegas clique known as the Rat Pack. The name was coined by actress Lauren Bacall years earlier, to describe a Hollywood drinking circle that included her then-husband Humphrey Bogart and Sinatra. The guys in the Rat Pack actually referred to themselves by a different name—The Summit—playing on a 1960 summit meeting in Paris between top world leaders.
13. Frank Sinatra reunited Jerry Lewis and Dean Martin.
In 1976, Sinatra appeared on Jerry Lewis’ annual Muscular Dystrophy Association telethon and surprised the host when he brought out Dean Martin, Lewis’s former comedy partner, from whom he’d been estranged for 20 years.
14. In Hollywood, Frank Sinatra was known as “one-take Charlie.”
Sinatra’s preference for approaching film roles in a spontaneous, rather than over-rehearsed, way earned him the nickname of “One-Take Charlie” in Hollywood.
15. Frank Sinatra threatened to have Woody Allen’s legs broken.
Sinatra was married to Mia Farrow from 1966 to 1968, and the two remained close friends. In Farrow’s autobiography, What Falls Away, she shared that when Sinatra learned of Woody Allen’s affair with Soon-Yi Previn, he offered to have the filmmaker’s legs broken.
16. A magazine claimed that Frank Sinatra got his stamina from Wheaties.
In 1956, Confidential magazine disclosed how Sinatra managed to satisfy so many Hollywood starlets—Wheaties! The article stated, “Where other Casanovas wilt under the pressure of a torrid romance, Frankie boy just pours himself a big bowl of crispy, crackly Wheaties and comes back rarin’ to go.” General Mills kept quiet as the tabloids talked up Wheaties’ power to fuel Sinatra’s exploits, and it wasn’t long before teenage boys were stampeding the cereal aisles.
17. Frank Sinatra had two hits called “New York, New York.”
Sinatra actually had two hits called “New York, New York.” The first was in 1949, from the film On the Town, and was written by Leonard Bernstein, Adolph Green, and Betty Comden. Thirty years later, Sinatra cut “(Theme From) New York, New York,” by John Kander and Fred Ebb. Originally from Martin Scorsese’s 1977 bomb New York, New York, Sinatra turned it into his signature song and onstage closer. He also angered the lyricist, Ebb, by customizing the words (Sinatra had done this to a few songwriters, most famously Cole Porter), adding the climactic phrase “A-number-one.” In 1993, Sinatra recorded the song again, this time as a duet with Tony Bennett.
18. Frank Sinatra hated being called “Chairman Of The Board.”
It’s a nickname he acquired while president at Reprise Records. According to his fourth (and final) wife, Barbara, Sinatra hated it.
19. Frank Sinatra wasn’t a fan of “My Way” or “Strangers In The Night.”
Barbara also maintains “My Way,” one of Frank’s most loved songs, did absolutely nothing for him. But that was a kind assessment compared to “Strangers in the Night,” which Frank called “a piece of sh*t” and “the worst f**king song I’ve ever heard.”
20. “My Way” has been covered by more than 60 people.
Sinatra may not have loved it, but “My Way” has been covered by more than 60 artists, including Elvis Presley, Aretha Franklin, and Sid Vicious. It has also been recorded in various languages.
21. Several people have died after performing “My Way.”
Since 2000, at least half a dozen people have been murdered after (or while) performing the Sinatra classic. Dubbed the “‘My Way’ Killings,” the strange phenomenon has gotten so bad that some bar owners have removed it from the selection list entirely.
22. Frank Sinatra inadvertently helped name Scooby-Doo.
At least according to former CBS exec Fred Silverman, who found inspiration in Frank’s signature “Scoo-Be-Do-Be-Do.”
23. Frank Sinatra directed the first Japanese/American co-production.
In 1965, Sinatra stepped behind the camera to make his directorial debut with None But the Brave, which was produced with Toho Studios. It was the first Japanese/American co-production filmed in the United States.
24. Frank Sinatra has a special place in New York Yankees history.
“New York, New York” has closed out every one of the Yankees’ home games since 1980.
25. Frank Sinatra had his own pasta sauces.
The year 1990 was a post-Paul Newman, pre-Marky Ramone time in celebrity spaghetti sauce, and leave it to Frank to fill the zesty void. But despite being inspired by his mother’s very own recipe, the sauce flopped. Thankfully, you can now find Mama Sinatra’s recipe online.
26. Frank Sinatra got first dibs on playing John McClane in Die Hard.
Think some action-loving Hollywood scribe came up with the concept for Die Hard? Think again. The movie is based on Roderick Thorp’s 1979 crime novel Nothing Lasts Forever, which is a sequel to his 1966 novel, The Detective. Because Sinatra had starred in the big-screen adaptation of The Detective, he had to be offered the role in its sequel. At the age of 73, he smartly turned it down.
27. Frank Sinatra didn’t like Marlon Brando, and Marlon Brando didn’t like Frank Sinatra.
Sinatra was always known as one of Hollywood’s most likeable stars, but Marlon Brando apparently didn’t agree. The two didn’t hit it off when they starred in 1955’s Guys and Dolls. Sinatra, who allegedly wanted Brando’s role in the film, referred to his co-star as “Mr. Mumbles,” while Brando nicknamed Sinatra “Mr. Baldy.”
28. Frank Sinatra briefly retired in 19671.
In 1971. Thankfully for you “Send in the Clowns” fans, his self-imposed exile from the entertainment industry lasted less than two years, before he returned for good with his comeback “Ol’ Blue Eyes is Back.”
29. There’s an asteroid named after Frank Sinatra.
The rock, called 7934 Sinatra, was discovered on September 26, 1989 by E. W. Elst at the European Southern Observatory.
30. Frank Sinatra sang one half of the only father-daughter tune to ever top the charts.
Sinatra has a unique distinction in Billboard history: He’s the “father” half of the only father-daughter duet to ever hit number one—thanks to “Something Stupid,” which he sang with Nancy.
31. Frank Sinatra was an honorary tribal chief.
Specifically, the “Order of the Leopard,” the highest honor in Bophuthatswana, a quasi-nation state in apartheid-era South Africa. The honor was a show of gratitude from president Lucas Mangope for Sinatra’s performances at the maligned—and later boycotted—Sun City casino.
32. The Beatles’s “Something” was one of Frank Sinatra’s favorite songs.
Frank may not have loved (okay, he hated) rock and roll, but he was a big fan of the George Harrison-penned “Something.” The song became a sample in Sinatra’s live set toward the end of his career.
33. The last song Frank Sinatra ever performed live is “The Best Is Yet To Come.”
On February 25, 1995, Sinatra sang the song for a group of 1200 people on the last night of a golf tournament named for him. The words “The Best is Yet to Come” are also on his tombstone.
34. Frank Sinatra reportedly took some Tootsie Rolls to the grave.
According to celebrity expert Alan Petrucelli, Ol’ Blue Eyes was buried with some Tootsie Rolls, along with a few other choice effects, including cigarettes, a lighter, and a bottle of Jack Daniels.
35. A provision in Frank Sinatra’s will helped to ensure it wouldn’t be contested.
In order to ensure that his passing wouldn’t lead to any legal battles, Sinatra’s will included a “no-contest” clause, which essentially says that anyone who contested it would be disinherited completely.
This story has been updated for 2020.