25 Wild Frank Sinatra Facts That Prove He Did It His Way

In honor of Sinatra’s 100th birthday, get a kick out of these fascinating facts about The Chairman of the Board.

It was a very good year for Frank Sinatra.

His upcoming 100th birthday on December 12th has been celebrated with an HBO documentary, a Grammy Museum exhibit, a Jack Daniel’s centennial whiskey, a Seth McFarlane-hosted tribute, and a televised concert featuring Tony Bennett, Alicia Keys, John Legend, Garth Brooks, Carrie Underwood and Usher performing live from—where else?—Las Vegas.

But amid all the gushing Sinatra salutes, it’s easy to overlook the fact that the “Chairman of Bad Attitude”, as Bono once called him, wasn’t always on his best behavior, even when he had the world on a string. Here are 25 wild Frank Sinatra facts that you really ought to know.  

1. He starred in a porn movie

Sinatra’s debut as an entertainer came in 1935 at the age of 19—in a porn loop, according to the 2011 biography Frank Sinatra: The Boudoir Singer. Sinatra was paid $100 to appear in The Masked Bandit, wearing a mask, of course. After he became famous, Sinatra was said to have “called his friends in the mob” to stop the blue movie from ever surfacing. 

2. He was arrested for sleeping with a married woman

In 1938, Sinatra was busted by the Bergen County, New Jersey sheriff and charged with carrying on with a married woman, which was actually a crime back then. The charge was later changed to adultery, and eventually dismissed.

3. He was notoriously well-endowed. 

Sinatra biographer James Kaplan recalls a memorable quote from the love of Sinatra’s life, actress Ava Gardner, in which she cracked that the young crooner was “only 110 pounds, but 10 pounds of it is cock!”

4.  He hosted  Rat Pack orgies in casino steam rooms

By the 1960s, Sinatra was bedding countless women, and even ran what amounted to a private brothel while in residence in Las Vegas. Sinatra hosted after-hours sex parties for the Rat Pack in a casino health club’s steam rooms, inviting star-struck showgirls or hiring hookers. His only rule, recalled pal Paul Anka in his 2013 memoir, My Way, was “no gang bangs.”

5.  He said that Angie Dickinson was the best sex he ever had

Out of all of his countless flings—not to mention his four marriages—Sinatra said the singer and actress Angie Dickinson reigned supreme. Casino owner Steve Wynn once asked Sinatra who was the best he ever had. Dean Martin was there, too, and, Anka writes in My Way, they both agreed: “Angie!”

6. He hated “Strangers in the Night”

Sinatra called it “a piece of shit” and “the worst fucking song I’ve ever heard.”

7. He inspired Scooby Doo

He inadvertently named the cartoon about a mush-mouthed, mystery-solving dog after CBS executive Fred Silverman heard “Strangers in the Night” ( “dooby, dooby doo…” ) on an airplane.

8.  He was monitored by the FBI  for decades

The FBI watched Sinatra, known for his mob ties and friendship with JFK, for almost 50 years, beginning when he was a teen idol in the 1940s, amassing 2,403 pages on him. In response to requests under the Freedom of Information Act, the hefty FBI file was finally released in 1998.

9.He was manic-depressive who attempted suicide four times

Frank described himself as an “18-carat manic depressive.” Despondent during a career lull in the 1950s, Sinatra tried to kill himself by sticking his head in an oven. He attempted suicide three other times during his tumultuous romance with Ava Gardner.

10. He loathed  his Chairman of the Board  nickname

His last wife, Barbara, said he couldn’t stand the moniker he acquired while president of Reprise Records.

11. He ordered underlings to hit people in the face

One night in the 1960s, Sinatra paid a waiter $50 to punch writer Dominick Dunne at a popular Hollywood restaurant. Another time, Sinatra ordered his valet to hit a woman in the face with a plate of barbecued spareribs after they argued about politics.  

12.He used his mob ties to help elect JFK

It was 1960, John F. Kennedy was stumping for the Democratic presidential primary in West Virginia, and his dad  Joseph Kennedy supposedly asked Sinatra to get mob boss Sam Giancana to deliver votes any way he could. The gangster came through with a mafia-fueled boost, but would live to regret it. After the Kennedys won the White House, Attorney General Robert Kennedy convicted 288 mobsters in 1963 alone.

13. He became a Republican after being dissed by JFK

Sinatra went ballistic when Kennedy  snubbed him for Bing Crosby on a visit to Palm Springs 1962. He had a helipad specially constructed on his roof in anticipation of the visit, and attacked it with a sledgehammer when he learned of JFK’s last-minute switch to Crosby’s place. Sinatra, a longtime Democrat who was the son of a Democratic ward boss, switched his allegiance to the Republican party soon after.

14. The Rat Pack called themselves  “The Summit”

With his swingin’ pals Dean Martin, Sammy Davis, Jr., Joey Bishop, and Peter Lawford, Sinatra led the hard-partying Vegas clique known as the Rat Pack. The name was coined by actress Lauren Bacall years earlier to describe the Hollywood drinking circle that included her then-husband Humphrey Bogart and future fling Sinatra. But the Rat Pack actually referred to themselves as “The Summit” after a 1960 summit meeting in Paris between top world leaders.

15. He turned down the title role of Dirty Harry  that went to Clint Eastwood

During a fight scene in his 1962 movie The Manchurian Candidate, Sinatra badly injured his hand, ruining his career as an action hero. Later offered the title role as a badass cop in Dirty Harry, he had to turn it down because of the injury’s lingering effects.

16. He considered having Woody Allen’s legs broken

When 50-year-old Sinatra married 21-year-old Mia Farrow in 1966, Dean Martin quipped,“I’ve got scotch older than her.” Sinatra later stunned Farrow when he served her with divorce papers in front of the cast and crew of Rosemary’s Baby, after she refused to quit the thriller to star in one of his movies. But in the early 1990s, after Farrow was publicly humiliated by Woody Allen’s relationship with her adopted daughter, Sinatra asked Farrow if he should hire someone to break the director’s legs.

17. He hated rock and roll

Sinatra called rock music “the most brutal, ugly, degenerate, vicious form of expression it has been my displeasure to hear.” He once said “Light My Fire” by The Doors was the worst record he ever heard.

18. But one of his favorite songs was by the Beatles

Sinatra loved the George Harrison-penned Beatles ballad “Something”. The song even became a sample in his live set toward the end of his career.

19.His epic Vegas binges put The Hangover to shame

One wild and boozy night at the Sands in 1967, Sinatra ran up a $500,000 gambling debt, then commandeered a golf cart and drove it straight into the glass entryway, smashing it to pieces. He later tried to set fire to some curtains with one of his trusty Zippo lighters but couldn’t get them to ignite.

20. He reportedly smuggled $3 million in cash for underworld pals

Beyond merely having ties to the mafia, Sinatra was said to have acted as a bagman for mob pals many times, and was once stopped at airport customs in New York with a briefcase containing $3 million in cash. However, federal agents decided to let him go after fans swarmed him, nearly causing a riot.

21. He had a longtime beef with Marlon Brando

Known for his many feuds over the years, one of the men Sinatra hated most was Brando. The Hollywood legend infuriated Sinatra when they co-starred in 1955’s Guys and Dolls. Sinatra hated his mumbling and method acting and thought Brando’s role in On the Waterfront should have been his.

22. He was a notorious neat freak and germaphobe

Sinatra showered several times a day and obsessively shaved, brushed his teeth and gargled with mouthwash. He also constantly doused himself with lavender water in to mask the familiar morning-after scent of cigarettes and whiskey.

23. He’s the subject of the most famous magazine profile of all time

Gay Talese’s groundbreaking profile, “Frank Sinatra has a Cold”, was reported in 1965 and published by Esquire in 1966. Taschen recently re-released the “New Journalism”-inspired essay as a coffee table book for its 50th anniversary.

24. He got sick of singing “My Way”

Sinatra’s signature anthem originated as a 1967 French pop song that was re-written for Sinatra by Paul Anka in 1969. It went on to be covered by such disparate artists as Sid Vicious (whose sneering version closes Goodfellas), the Three Tenors, Elvis Presley and The Pogues. Sinatra frequently trashed the song onstage, once telling a Los Angeles audience before singing it:  “And of course, the time comes now for the torturous moment not for you, but for me.”

25. But he never tired of “The Best is Yet to Come”

At Sinatra’s Palm Springs funeral in 1998, he was buried with a flask of Jack Daniel’s, a pack of Camels, his Zippo lighter, a roll of dimes, Tootsie Rolls, Life Savers and a gold Bulgari medallion, a birthday gift from Barbara, inscribed in Italian: “You still give me a thrill.” His tombstone reads “The Best Is Yet to Come.” The song was also the last he ever performed live, before 1,200 people at a golf tournament named for him.