Connery, Sean Connery. Known for his paradoxical mixture of rough-and-tumble Scotsman combined with graceful self-possession, Connery was highly esteemed in the film world before his recent passing—but his life was not without a handful of scandals and adventures. Get ready to take these suave facts about Sean Connery shaken, not stirred.
1. He Was A Man Of Many Names
Long before he was James Bond, he was Thomas Sean Connery. At first, friends called him “Tommy,” but he eventually chose to go by his middle name, Sean. More remarkable was his other nickname, “Big Tam,” which friends gave to him because of his size. At 12, Connery was already towering over his peers. By the time he was 18, he had reached his full height—a sturdy 6’2” tall.
2. He Started Young
Sean Connery was born to a working class family in Scotland—his father was a factory worker and truck driver and his mother was a cleaning woman. Young Sean also rolled up his sleeves and got to work and help the family. Before he was even 16 years old, he got his first job, as a milkman in his hometown of Edinburgh.
Connery never stopped working after that. However, it was a long and bumpy road before he found his calling…
3. …In More Ways Than One
Connery was definitely a ladies’ man—and he got started very early. The actor revealed that he lost his virginity when he was 14 years old to an older woman who was working for the ATS (Auxiliary Territory Service), a woman’s branch of the British Army that operated during WWII. She might have had an influence on him in other ways, too…
4. He Became A Sailor
Connery had been too young to enlist and serve his country during WWII, but that didn’t stop him from joining the Royal Navy the moment that he turned 16 years old. He jumped right into the culture, immediately getting two tattoos. One tattoo was a tribute to his family, while the other read “Scotland Forever”. Most people have an awkward teenage phase, but Connery was already a 6’2” tall tattooed lothario at 16…life isn’t fair.
5. It Was A Devastating Hardship
Connery threw himself into his new life as a Navy man, training at the gunnery school and working with an anti-aircraft crew. Three years in, and Connery was totally dedicated—until it was suddenly all ripped away from him. He began suffering from a painful duodenal ulcer, and the Royal Navy discharged him as a result. Still just a teen, he kept searching for his place in the world.
6. He Did A Bit Of Everything
After the Navy discharged him, Connery returned to Edinburgh, where he worked as a truck driver, lifeguard, coffin polisher, and as a model at the local art school. It made sense, as Connery spent most of his spare time working on his physique. He was a bodybuilder in those days, and even entered competitions. He never made it far, because one of his other passions got in the way…
7. His Physicality Won Him A Lot Of Attention
Most of the American bodybuilders that Connery faced in competition refused to participate in any other physical activity that would affect their muscle mass. However, like many Scots his age, Connery couldn’t be torn away the football field. He played with a couple of teams, and he must have been good, because one day, a life-changing offer arrived at his feet.
8. He Was Almost A Red Devil
When he was 23 years old, the manager of the Manchester United football team offered Sean Connery a spot on the legendary club—a dream come true for any young footballer in the UK. However, Connery’s elated reaction soon turned to doubt. It would be a lot of money for a poor kid from Edinburgh. However, Connery also knew that footballers tended to peak at 30.
He made the difficult decision to turn it down…but he did have a plan on the backburner.
9. He Found Another Passion
While he was still part of bodybuilding competitions, a friend told Connery that a production of South Pacific was holding open auditions nearby. He got a job as a chorus boy and as the production continued, he moved his way up through the ranks. Connery began to see it acting as a viable career, but his road to fame was not without its ups and downs.
10. He Fell In Love
Connery’s time appearing in South Pacific brought him some financial independence, access to other roles, and a slew of new friends…and it also brought him love. He began to date a beautiful dark-haired woman by the name of Carol Sopel—but their fairytale romance was doomed to a heartbreaking end. Sopel was Jewish, and her family didn’t approve of Connery.
They told him to stay away from her, and the relationship ended as quickly as it began—and his problems didn’t end there.
11. He Was A Target
Growing up poor in Edinburgh, Connery had seen his fair share of trouble—but that all amounted to nothing compared to the one terrifying encounter that made him a local legend. One night at a pool hall, some members of the infamous Valdor gang attempted to take his jacket. When he stopped them, their reaction was utterly chilling. Six of them followed Connery home in the dark—but they had no idea what they were in for.
12. He Fought Back
Connery realized what was happening. He made the quick decision to take the group on, even though he was all by himself. He took each gang member down one by one until he was the last man standing. It was enough to earn him the respect of the notoriously violent gang he’d taken on, and he gained a reputation among locals as a “hard man”.
13. He Dedicated Himself To His Craft
When Connery wasn’t singlehandedly fighting off a gang of attackers, he was ardently studying the works of Shakespeare, Ibsen, Tolstoy, and Proust, all in hopes of becoming a serious actor. He also took elocution lessons to shake off the working-class brogue. Despite all his hard work, Connery still struggled.
14. He Climbed The Ladder
In the 1950s, Sean Connery was hustling. He was appearing in stage plays, bit parts in movies, and small roles on TV, while also babysitting on the side to make ends meet. As time went on, filmmakers gave him larger roles that reflected his rough-and-tumble presence and working class background, playing truck drivers and boxers.
Finally, his big break came. Producers cast him opposite starlet Lana Turner in Another Time, Another Place—but behind the scenes, things weren’t always so smooth.
15. She Got Him Into Trouble
While making the film in England, Connery took it upon himself to show Turner, an American, around London. Turner’s boyfriend, gangster Johnny Stompanato, began to suspect that the pair were having an affair, so he flew from Los Angeles to London to check in on them—and things quickly got out of hand. An enraged Stompanato threatened Connery with a gun. Big mistake.
16. He Didn’t Know Who He Was Up Against
What happens to people who threaten Sean Connery? Well, historically, it hadn’t really gone well for them, and this time was no different. When Stompanato came at Connery, the Scotsman immediately disarmed him and knocked him down. Producers banned Stompanato from the set of the film, and soon after, Scotland Yard officers arrived to personally take him to the airport.
The UK authorities then deported Stompanato. The lesson? Don’t mess with Sean Connery.
17. He Knew How To Wear A Kilt
Compared to many of his fellow actors, Connery was quite rugged and rough. This often worked in his favor with the ladies, but when he met photographer Julie Hamilton, it had the complete opposite effect. She confessed that she thought he was appalling—until one moment, and piece of fabric, changed it all. Once Hamilton saw Connery in a kilt, she changed her tune, declaring him the most handsome man she’d ever seen.
Bet not a lot of other men get that reaction when they don the Highland regalia.
18. They Both Fell Hard
Connery had been in love with Hamilton for months. Finally, she opened her eyes and realized that she felt the same way. They moved into a small apartment in London together and met each other’s families. Hamilton supported Connery as he struggled to become a serious actor—but the relationship was far from one-sided.
19. He Made Huge Sacrifices
In 1960, Hamilton fell ill, and the diagnosis was dire—she had tuberculosis. At the same time, producers had approached Connery with an incredible offer. They wanted to give him a star-making role in the Charlton Heston film El Cid. Faced with a difficult decision, Connery made a heartbreaking choice. He turned down the part in order to care for Hamilton as she recovered.
Luckily, the studio decided to give him a second chance, and the decision didn’t derail his career.
20. There Was Someone Else
Everyone expected Sean Connery and Julie Hamilton to get married—until one day, when it all fell apart in an instant. As Hamilton later revealed, she was in bed with Connery when he offhandedly remarked, “What incredible eyes Diane has got”. At the time, he was working on a teleplay with (married) actress Diane Cilento.
Hamilton immediately knew something was wrong, and confronted the actor.
21. He Made Good On His Word
Connery confirmed Hamilton’s worst fears, admitting that his love for her had faded. She walked out. Their relationship ended then and there, much more quickly that it had begun—but their story wasn’t over yet. Years later, the exes ran into each other. By then, Hamilton was married and had a child, a son she named Jason.
In an off tribute to how Hamilton had supported him when he was a struggling actor, Connery made a vow to her. He said that he would one day name his own child Jason.
22. She Changed His Life
While falling for Diane Cilento presented its own problems—for one, she was married—it also had an unexpected side effect. Cilento was the one who introduced him to producer Harry Saltzman, who was hoping to bring the beloved character of James Bond to the screen for the very first time. However, it wasn’t as easy as simply meeting a producer and landing the role of a lifetime. Connery had to work for it.
23. It Wasn’t Easy
First off, Bond creator Ian Fleming was at odds with the film producers over who to cast. While they envisioned Cary Grant, he would only commit to one film, and they wanted to create a franchise. Then, the filmmakers created a “Find James Bond” contest, even going so far as to declare a winner, before realizing he didn’t have the acting chops for the role.
It was then that they began to consider Connery—and he came up with a plan to make a lasting impression.
24. He Pulled It Off
When we think of 007, we think of dark, well-tailored suits, coiffed hair, and debonair manner—but when it came time to audition for Bond, Sean Connery went rogue. He showed up in rumpled clothes and acted in his typical rough manner. Somehow, it worked. The producers cast him for the first-ever Bond film, Dr. No. The role would go on to change the entire course of his life.
25. It Made Him An Icon
Connery had already spent years refining his working-class accent, and when producers cast him as Bond, they gave him a crash course to round it all out, hoping to make him a “dapper, witty, and above all cool” gentleman. The UK already had Bond mania, but it was important to the filmmakers that they create an absolutely unforgettable introduction to the 007 character.
This was how they ended up coming up with the iconic scene where the character of Sylvia Trench asks the agent for his name and Connery answers: “Bond…James Bond”.
26. Everything Was Coming Together
When Dr. No became a huge hit, Sean Connery was flying high in more ways than one. Just before studios relased the movie, Cilento obtained a divorce from her first husband. Soon after, Cilento got pregnant, and Connery proposed to her. With so much fanfare over Bond in the UK, the pair organized a secret wedding in Gibraltar—but it didn’t exactly go as planned.
27. They Nearly Had To Cancel
At the time, political tensions were running high in Gibraltar—and it nearly led to disaster for the young couple. Connery and Cilento traveled there separately, and border officials detained Cilento when they found an error in her passport. By the time that they released her, she’d missed her ferry to Gibraltar—and it looked like she’d miss the wedding ceremony too.
Luckily, she finally made it over to Connery, and the pair got married…but it wasn’t necessarily happily ever after.
28. They Started A Family
After Connery and Cilento’s son was born, Connery made good on his promise to his ex-girlfriend Julie Hamilton. He named the boy Jason. With her husband cast in one of the biggest roles out there, Cilento chose to let her own acting career take a backseat in order to support Connery and raise Jason. Connery had them both on set with him for From Russia With Love, the next Bond film, which became a massive hit.
29. He Made An Impression
While Ian Fleming was initially unsure about Sean Connery—he wanted Roger Moore—Connery eventually won Fleming over. Before his passing in 1964, the author began to change the character slightly to reflect what Connery had brought to the role, most notably giving the spy more of a sense of humor.
30. He Didn’t Want To Be A Spy Forever
While the success of the Bond films made Sean Connery a superstar, it also stirred up anxiety and fear. Even before producers had given him the part, Connery had worried that taking on five films as Bond would cause him to become typecast. Cilento had convinced him to do it anyway. It was a decision she’d come to look back on with deep remorse.
31. It Blew Up
In 1965, Cilento announced that she was leaving Connery and taking their son and her daughter from her first marriage with her. Connery’s reaction was utterly cold-blooded. He packed his bags and left the family home before Cilento could. On the set of the fourth Bond film, Thunderball, they reunited—but things were never really the same again.
32. They Were At Each Other’s Throats
Many who worked on the film said that they heard the couple getting into loud fights on set. Things didn’t get better when they returned home. Connery was now a mega-star, and Cilento’s career was floundering. They were very competitive with each other, but they still stubbornly tried to keep the marriage going. It was only a matter of time.
33. He Wanted To Branch Out
The Bond films were such huge hits that they did give Sean Connery quite a bit of leverage in Hollywood. He first used this power to force his studio overlords to get him a part in the Alfred Hitchcock film Marnie. With just two Bond movies left in his contract, Connery began to breathe a sigh of relief that he might have a career beyond Bond.
But you know what they say—just when I thought I was out, they pull me back in again (different film franchise, but it still applies).
34. He Knew It Was A Bad Idea
Long before there was Tom Cruise, Sean Connery opted to do many of his own stunts for the Bond movies—but on the set of Thunderball, it nearly cost him his life. In one scene, Connery was supposed to swim through a pool of sharks. Connery immediately expressed his reservations.
35. It Was A Close Call
As a result, filmmakers constructed a specially-built plexiglass partition for the actor, so that he’d be separated from the sharks. There was just one problem. They didn’t have quite enough plexiglass. As a result, one of the sharks slipped through into the area where Connery was swimming. He quickly jumped out of the pool, narrowly escaping a bloody fate.
36. His World Was Not Enough
Connery had started out the 60s on top of the world, newly married and cast in a star-making role as Bond. But by the turn of the decade, he was frustrated and he wanted more out of life. Not only was his career unfulfilling, his marriage was also falling apart. Finally, it all came to a turning point.
37. He Broke Ties
Before Connery even arrived on the set of You Only Live Twice, he made it clear to the film studio that he was done with James Bond. They prepared themselves to find a replacement. It’s unknown if his wife Diane Cilento took it as well when she and Connery finally separated in February 1971. Either way, Connery wasted no time in moving on…
38. He Was In The Middle Of A Love Triangle
After his divorce from Cilento, Connery became quite the ladies’ man, dating actresses Lana Wood, Magda Konopka, and Jill St. John, among others—but the dating pool in Hollywood is surprisingly small, and he stirred up quite a bit of trouble. While making Diamonds Are Forever in 1971, Connery dated two of his co-stars simultaneously—the aforementioned Wood and St. John.
The two have had a well-publicized feud since the 80s. However, many trace their hatred back much longer, to their competition over Connery back in 1971. Whoops!
39. He Fell In Love Again
Connery dated around following his divorce, but for years, only one woman caught both his eye and his heart: painter Micheline Roquebrune. There was just one problem. When they met, they were both still married to other people. Their relationship stayed on the back burner until each got their respective divorces, and then they were off to the races. Or, more accurately, the altar.
40. He Tricked Them
The press was all over Connery and Roquebrune. They expected the couple to get married in early 1974. However, Connery was determined to throw them off, so he came up with an ingenious plan. In March 1975, he told the press that they were already married, and the ceremony had taken place four months earlier—a complete fabrication. Two months later, they finally wed…but there was a bizarre twist.
Connery chose to wed Roquebrune at the same place he’d married his first wife, Gibraltar. I guess he just really liked it there?
41. He Broke Ground
Connery has the unexpected distinction of being part of one of the first male-on-male kisses on television. In the 1960 TV movie Colombe, Connery’s character accuses his wife of having an affair with his brother. In a pivotal scene, he kisses his own brother to see what all the fuss was about. Even though the kiss was not romantic, it was still one of the first of its kind!
42. He Surprised Everyone
After Connery left the role of James Bond, producers signed up George Lazenby for a seven-film contract as the suave spy—but Lazenby immediately crashed and burned, and left the role after just one film. Connery had struggled incredibly hard to get away from the 007 character. It was a shock to fans, insiders, and perhaps even himself when he agreed to return to the role in 1971. But he had his reasons…
43. He Did It For A Good Cause
First off, Connery asked an exorbitant fee in order to come back to Bond. He also demanded that he get to do two films of his own choosing immediately following the completion of the seventh Bond film. When the studio agreed, Connery took the money and used it to establish a trust to support fellow Scottish artists.
44. He Had Pick Of The Litter
With Diamonds Are Forever out of the way, Connery was free to move on to whatever projects he desired. He helped director Sidney Lumet make one of his first films and appeared opposite his close friend Michael Caine in The Man Who Would Be King. He played Robin Hood and got to participate in an Agatha Christie adaptation with a star-studded cast. Connery was on top of the world—but that didn’t mean they were all hits.
45. He Nearly Bared It All
In 1974, Connery made his weirdest appearance yet, in the bizarre sci-fi thriller Zardoz—best known for Connery’s costume of a scarlet mankini, some 40 years before Borat hit the scene. According to writer and director John Boorman, Connery had actually had a hard time finding work after leaving the Bond franchise, which is why he did the film.
While critics panned it at the time, it’s become something of a cult classic. I blame the mankini.
46. He Went Back To Where It All Started
By the 80s, Connery’s star status was set in stone. The sour taste of being the first Bond must have left his mouth, because he agreed to take on the role again for 1983’s Never Say Never Again. Connery’s wife had suggested the very-appropriate title. The star had once stated that he would “never again” play Bond. He probably should’ve stuck to that vow…
47. They Barely Made It Out Alive
The making of Never Say Never Again was an utter disaster—and Connery was at the center of it all. He demanded rewrites of the script, hand-picking the screenwriters himself. During the production, it became clear that the film’s producer was in over his head. As a result, Connery took over many production duties. As if that wasn’t bad enough, the film’s fight trainer accidentally broke Connery’s wrist while training.
That fight trainer? None other than Steven Seagal.
48. He Made A Comeback
After that horrible on-set experience, Connery really did say “Never again,” but this time, he meant it—and not just about Bond. He actually took a two-year break from making films—but when he returned, it was with a vengeance. First, he appeared in The Untouchables, for which he won an Oscar for Best Supporting Actor, and then he took of the role of Indy’s father in Indiana Jones and the Last Crusade.
Once again, he was on top…but for how long?
49. His Private Life Became Public
In 1993, fans were shocked when the tabloid pages descended on Connery yet again. A singer-songwriter by the name of Lynsey de Paul had made a shocking revelation, claiming that she’d had an ongoing affair with the married movie star in 1989—and the details were chilling. She claimed that he’d first flirted with her and asked for her number as his wife sat right beside him.
According to de Paul, he left her high and dry after five months. She said that their romance was one of the biggest regrets of her life. Connery denied the affair, but the story didn’t end there.
50. It Happened More Than Once.
Another woman also came forward and claimed that she’d had an ongoing affair with Connery. Danish journalist Helle Byrne said that they’d met when she interviewed him for a magazine, and that their affair had lasted 11 months before it ended. Once again, Connery denied it, and his wife stood by his side, remaining silent on the subject ever since.
51. He Almost Didn’t Become Sir Sean Connery
In the late 90s, Connery was on the shortlist for contenders for knighthood—until a controversy derailed it all. Connery had been a fierce supporter of Scottish Independence from Britain. As a result, political opponents made sure that he was vetoed for knighthood in 1997 and 1998. However, he clawed his way back onto the list in the year 2000, and the Queen finally knighted him that year.
52. He Gave Up
Sean Connery appeared in all kinds of films throughout the late 90s and early 2000s, but one project was so disastrous that he left Hollywood completely afterward. Connery took a part in the long-awaited film adaptation of The League of Extraordinary Gentleman, but the production was a catastrophe from the very start.
Connery clashed with director Stephen Norrington in a big way, and they nearly came to blows on set—but their feud didn’t stop when the film was done.
53. He Had A Way With Words
When Norrington skipped a release party for the film, a journalist asked Connery where the director was. His reply was utterly savage. Connery told the writer to “Check the local asylum”. While he made no formal announcement at the time, Connery effectively retired from making movies after The League. He never appeared in another live-action movie again.
54. He Left Hollywood In Anger
Three years later, in 2006, Connery finally confirmed his official retirement from acting, and he didn’t hold back with what he thought, saying that “the […] idiots now making films in Hollywood” had caused him to never want to make a movie again.
55. He Wore A Piece
Sean Connery has topped many critics’ lists as their pick for the best Bond—but there’s one behind the scenes secret that few fans know. Connery began losing his hair at a very young age, and every time that he played 007, he actually wore a toupee.
56. Their Relationship Was Horrible
In 2006, Connery’s first wife Diane Cilento published her autobiography, and in the book, she made disturbing accusations about the star. Cilento claimed that Connery had both physically and mentally harmed her during their marriage. Connery denied the accusations, saying “I don’t believe that any level of abuse of women is ever justified under any circumstances”—but that wasn’t all.
57. He Said Some Very Questionable Things
To make matters worse, journalists unearthed quotes from an old interview with Connery. In 1965, the star had said: “I don’t think there is anything particularly wrong in hitting a woman, though I don’t recommend you do it the same way that you hit a man”. On top of that, Connery had told Vanity Fair in 1993: “There are women who take it to the wire. That’s what they are looking for, the ultimate confrontation. They want a smack”. Yikes.
58. They Suspected Him
Remember Connery’s disturbing confrontation with Johnny Stompanato on the set of one of his first films? Well, their story didn’t end when Stompanato returned to the US. Soon after, someone fatally stabbed Stompanato in his girlfriend Lana Turner’s home—and one of the people closest to him made a chilling accusation. While law enforcement detained Turner’s daughter for the attack, Stompanato’s boss, Micky Cohen, thought there was no way a teenaged girl could’ve done it.
Cohen suspected that Connery was the culprit…and he wanted revenge.
59. He Was In Grave Danger
When this was all occurring, Sean Connery was in the US working on a Disney film. Cohen actually went so far as to take out a hit on Connery—but as we know, messing with the original Bond is never a good idea. Connery moved hotels when he received a threatening call at the Roosevelt where he was staying, but other than that, he didn’t let the intimidation bother him.
Cohen eventually called off the hit after a judge found Lana Turner’s daughter guilty, and Connery went on with his life. The man was basically bulletproof!
60. The World Lost An Icon
On October 31, 2020, Connery’s family and the production company behind the James Bond films jointly announced that the actor had passed on peacefully in his sleep at the age of 90. Later, Connery’s wife Micheline Roquebrune made a heartbreaking revelation about the star’s final years.
She shared that: “He had dementia and it took its toll on him. He got his final wish to slip away without any fuss. It was no life for him. He was not able to express himself”. RIP.
Sources: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38