Although Peter O’Toole was one of Hollywood’s most respected actors, behind the scenes, his debaucherous lifestyle was so wild—it became the stuff of legend. From wild onset antics to scandalous affairs, O’Toole toed a dangerous line. His excessive drinking only exacerbated his bad choices, and he was notoriously reckless with the hearts of those who cared for him most.
An unapologetic inebriate and proud carouser, O’Toole famously said, “The only exercise I take is walking behind the coffins of friends who took exercise.”
1. He Had A Crooked Father
Peter O’Toole was born in Leeds, Yorkshire, England on August 2, 1932, and his upbringing was interesting, to say the least. Overflowing with moral contradictions, O’Toole’s father was both a Catholic and a gambler. This exposed young O’Toole to a freewheeling lifestyle at a very young age. Like his father, he too, would one day become a notorious risk-taker.
2. He Followed A Gambler
When he was still a baby, O’Toole’s father packed up the family and took them on a five year tour of Northern England. Of course, this wasn’t some extended vacation…Instead, his dad bounced from one racecourse town to the next—in search of an income from gambling. As unstable as his home life seemed, O’Toole’s childhood was about to take an even darker turn.
3. He Had An Odd Fear
The beginnings of the 1940s were a scary time in Europe. With the dawn of WWII, Germany became a very real threat, and parents wanted to keep their children safe. For their own safety, both O’Toole and his sister were evacuated from Leeds and sent straight to Catholic school. But instead of feeling a sense of security, he developed an intense fear of the nuns in charge.
He later said, “I used to be scared stiff of the nuns: their whole denial of womanhood—the black dresses and the shaving of the hair—was so horrible, so terrifying.”
4. He Turned His Back On Religion
O’Toole may have been afraid of nuns, but it certainly didn’t turn him off all women. In fact, he completely turned his back on notions of chastity and ran in the opposite direction…straight into the arms of an older woman with a scandalous occupation. Fed up with religion and its constant strictness, he decided to embrace “sin” for all its worth.
Peter O’Toole might just be the wildest hellraiser of his time—but his good-time lifestyle came at a tragic cost. Endless affairs. Excessive drinking. Shameless extravagance.
5. He Met An Unforgettable Stripper
O’Toole lost his virginity at a very young age, and in a very surprising way. He was only 13 years old when he met a willing stripper name Bubble LaRue. When it came to intimate expertise, Bubble was O’Toole’s first mentor, and she taught him everything. His willingness to try new things—his libertine attitude—prepped O’Toole for his infamous career in Hollywood.
6. He Tried Everything
O’Toole wasn’t afraid of work, and attempted many different professions. He tried being a warehouseman, a copy boy, a messenger, and finally a reporter—but not a very good one. His frustrated editor at the Yorkshire Evening Post fired him with these words: “Try something else, be an actor, do anything.” So, O’Toole did just that.
7. He Was A Natural
O’Toole set his mind to acting and eventually secured a scholarship to The Royal Academy of Dramatic Art which catapulted his career and set him on a path toward true love. When it came to acting, he was a sure-fire natural, and so, it came as no surprise when O’Toole cemented his reputation as a fine Shakespearean actor. Before long, he was flourishing, and the good news was—his luck had only just begun.
8. He Found His Silver Lining
O’Toole met his future wife, Sian Phillips, on the set of an uninspiring production called The Holiday. While the project was an overall dud, she became O’Toole’s silver lining and before long, they started going steady. However, Phillips soon realized that her boyfriend was quite the eccentric. Even so, she was oddly drawn to his volatile personality. She just couldn’t get enough.
9. He Was A Weird One
O’Toole’s temperamental behavior surfaced in all kinds of weird ways, and his infatuated girlfriend was usually on the receiving end of it. On one shocking occasion, he decided that he hated her clothes—specifically that she wore too much purple and black. To drive his point home, he proceeded to throw all her clothes out the window and onto the street. But Phillips’ reaction wasn’t what you might expect…
10. He Dressed Her Up
Instead of flying into a rage, Phillips turned to her crazed beau and asked him, “What will I wear now?” O’Toole was ready with his answer: She should wear his clothes. Instead of telling him to get lost, Phillips took him up on his offer, and started wearing his trousers, plaid shirts, fisherman’s sweaters. But when it came to his control issues, O’Toole was just getting started.
11. He Had A Dangerous Vice
Early in his career, O’Toole became hooked on one particular vice—drinking his face off. His habit became so extreme that he often drank a full bottle of brandy before bed. There was no doubt about it—indulgence was his number one hobby. However, there was one distinct problem. His lovely girlfriend wasn’t a drinker at all. In fact, she was his exact opposite, always prim and proper…but not for long.
12. He Was A Bad Influence
O’Toole had Phillips completely under his spell. With his magnetic sense of humor and piercing blue eyes, she was a total goner. She soon realized that if she didn’t partake in at least a little Guinness, she’d miss out on all the fun. But even though she adopted his bad habit, O’Toole moved to the beat of his own drum. Poor Phillips just couldn’t keep up.
13. He Went Missing In Action
Even though he’d roped his girlfriend into excessive drink, O’Toole still went on benders without her. After having disappeared for days on end, he’d reappear in the wee hours of the morning—inebriated and in search of a hot breakfast. Phillips would have no idea what he’d been up to, and with who. Occasionally, however, he’d invite her along for the ride.
14. He Whisked Her Away
One morning, O’Toole showed up at their home in a sports car that he hadn’t had when he left. It was brand new, and O’Toole was shouting at Phillips to get her passport. Apparently, they were off to Europe. With barely time to pack, O’Toole and Phillips went on a grand mystery tour that included Switzerland, Holland, Germany, and Austria. And it when it came to surprises, he had another one tucked into his back pocket.
15. He Popped the Question
While a marriage proposal is usually considered a grand gesture, O’Toole managed to imbue the occasion with absolutely zero romance. There was no proclamation of love: He simply asked her to bear his children. Unsurprisingly, Phillips’ friends were against it, saying that she would get lost in his over-the top-personality. But their warnings fell on deaf ears, and Phillips wed O’Toole in 1959.
16. He Made It A Night To Remember
By 1960, Phillips decided to put her acting career on hold, and play wife to O’Toole. She soon gave birth to daughter Kate—and the occasion was definitely one to remember. O’Toole, in typical form, arrived at the hospital—completely wasted—followed by a troupe of rowdy actors. Together, they sang a drunken song to welcome the newborn baby. But that wasn’t all.
Next, O’Toole picked up his father, and drank even more. Later, these two partiers were found passed out cold. Unfortunately, as his drinking became more and more of a problem, it even started to sabotage his performances…
17. He Rewrote Shakespeare
Drinking before a stage appearance wasn’t out of the realm of possibilities for O’Toole—but usually he got away with it. One time, however, while appearing in a Shakespearean play, he messed up big time. He was acting in The Merchant of Venice, but his inebriated mouth started spouting lines from King Lear. Oops. I guess the Bard was rolling in his grave that night.
In terms of onset antics, however, this definitely wasn’t O’Toole’s first time at the rodeo…
18. He Was A Prankster
In one stage play O’Toole was in, he had to stand offstage while his onstage co-star, Wendy Williams, gazed thoughtfully at his silhouette. One night, as Williams was staring at him, O’Toole pulled a banana out of his pants, took a pair of scissors, cut the top part off, and ate it. Williams only saw this in silhouette, and assumed the worst. She fainted right on the set.
Although his pranks often garnered laughter at work, his wife found it harder and harder to reconcile his many other shortcomings.
19. He Exposed Her
Unfortunately, O’Toole’s “happily ever after” didn’t come without its struggles. Notably, he obsessed over his wife’s relationship history. Remember, Phillips was quite refined when she met O’Toole, and wasn’t comfortable talking about it—especially in front of his friends. Never one to play by the rules of decorum, O’Toole shamelessly spoke about Phillip’s past without her consent. Not cool O’Toole, not cool.
20. He Was Dangerously Magnetic
After O’Toole aired his wife’s dirty laundry in public, her embarrassment got the best of her, and she finally decided to leave him. Of course her resolution lasted about a second before she changed her mind. Like a love-addled boomerang, Phillips always came back. No matter his mistakes, O’Toole always found a way to keep her hooked.
21. He Said Yes To Insta-Fame
Marlon Brando said no, and so did Albert Finney. So, in 1960, they offered the role to O’Toole—who happily gave it a big yes. The film was Lawrence of Arabia, and the role was T.E. Lawrence himself. Of course O’Toole didn’t know it then, but this sand and camel epic would be a career defining role for him. O’Toole must’ve had a good feeling about the part, because after accepting it, he bought his wife a very expensive gift.
22. He Took It Back
Nothing says “Merry Christmas, and I got a lead role in an epic film” like a brand new car—complete with a pretty bow. This luxury gift blew Phillips away, but she was in for a nasty surprise. She took the car for a short spin…and then never saw it again. O’Toole took the car from her, visited some friends in Bristol, and then, after some heavy drinking, rear-ended a squad car.
To Phillips dismay, he ended up behind bars. But if O’Toole didn’t take his private life seriously, at least he took his acting seriously…Right? Well…sort of.
23. He Became Lawrence
Preparing to play the real Lawrence of Arabia was a massive undertaking. O’Toole couldn’t do anything about their differences in height—he was eight inches taller than Lawrence—but he did do an extensive amount of research. He learned how to ride a camel, taught himself basic Arabic, lived in a Bedouin tent, and read everything he could find about the writer, archeologist, and officer. O’Toole was ready to perform, but was the cast ready for him?
24. He Renamed A Legend
The time had finally come to start filming Lawrence of Arabia. O’Toole’s co-star was Egyptian actor Omar Sharif, who would later go on to break audiences’ hearts in Doctor Zhivago. When O’Toole met Sharif, he refused to believe that that was his real name. O’Toole said that no man could be named Omar Sharif, so he rudely called him Fred instead. But that’s not all.
Later, O’Toole extended the nickname to Cairo Fred. Sadly, his bad behavior in the desert didn’t stop there.
25. He Had A Sitter
The director of Lawrence of Arabia was well aware of O’Toole’s terrible reputation, so he did something drastic: He hired a babysitter. The film shoot was going to last two years, and someone had to keep O’Toole fit for work—and that meant sober. Something tells me that the babysitting job was a bit like herding kittens. Well, sitter or no sitter, it seemed that nothing could keep O’Toole away from the bottle.
26. What Happens in Beirut…
O’Toole did have days off during the two year shoot in Jordan, and even then, he managed to get into trouble. He and Sharif were an extremely dangerous pair, and they often spent their down time together. Once, they flew in Sharif’s private jet to the Las Vegas of the Middle East—Beirut. Rumor has it that the two of them spent an outrageous amount of money…
In a single night of partying, they spent nine months’ wages. This fact, however, pales in comparison to one of their even greater blunders.
27. He Tried To Pick Up A Nun
On one of O’Toole and Sharif’s escapades, the pair was searching for some companionship—of the female variety—and visited a bordello. O’Toole and Sharif, handsome as they were, couldn’t get any of the girls there to even notice them. And that was when they realized their mistake: It wasn’t a bordello they were in—it was a nunnery.
But this was just another day in the company of O’Toole. To anyone that knew him, his bad behavior was pure legend.
28. He Was Out Of Control
O’Toole’s penchant for debauchery certainly had a a wow factor. His Lawrence of Arabia costar and friend, Alec Guinness, watched O’Toole distastefully handle himself at a cast dinner: He fondled women’s behinds, started fights, and sprayed champagne everywhere. Later, Guinness said, “O’Toole could have been killed–shot, strapped or strangled–and I’m beginning to think it’s a pity he wasn’t.”
29. He Was Number One
O’Toole didn’t have a global audience until he appeared in Lawrence of Arabia. It was a huge break for him, and resulted in an Academy Award nomination, a BAFTA award, and the number one spot in Premiere magazine’s top 100 Greatest Performances of All Time. But awards aside, O’Toole also won something else: Riches beyond his wildest dreams.
30. He Went Extravagant
Once Lawrence of Arabia had defined him as a big star, O’Toole’s life took a turn for the extravagant. He and Phillips now had a full staff of secretaries, au pairs, cleaners, chauffeurs, and gardeners. They collected art by Picasso, and had four cars. With money in the bank, O’Toole’s taste became more and more expensive, while his unpredictable antics became more and more reckless.
31. He Had TV Tantrums
Phillips wisely placed a basket of ping pong balls next to their TV—so O’Toole would have something to throw at it when he didn’t like what he was watching. Sound ridiculous? Yes. Was it necessary? Absolutely. Turns out, the first time O’Toole threw something at the TV, it was something a lot more expensive than ping pong balls: It was another TV. He threw their small portable through the main set.
But wait. There’s more.
32. He Had A Secret Hiding Place
During the filming of Lawrence of Arabia, O’Toole picked up a habit of collecting antiques. One time he was bringing a pair of earrings from Greece that he knew he should hide from the border authorities. He needed an unusual place to hide them—but where? To put it bluntly, he hid the earrings in his underwear—and in a hiding place that circumcised men don’t have.
Still, his dangerous exploits didn’t exploits didn’t end there.
33. He Threatened A Star
Being a film star was fine, but O’Toole still wanted to do live theater. His drinking, however, was making that difficult and, in this particular situation, even dangerous. The play was Hamlet, and O’Toole had a sword fight at the end of the play with actor Derek Jacobi. To avoid onstage injuries, the fight was carefully choreographed.
But to nobody’s surprise, O’Toole was often intoxicated, and didn’t follow the choreography. Jacobi said that every night he was literally fighting against O’Toole—for his life.
34. He Made A Dirty Wager
O’Toole had quickly become famous overnight, and his reaction to all the female attention put him into a kid-in-a-candy-store sort of mentality. A friend of his, impressed by O’Toole’s luck with the ladies, made him an outrageous bet. He put money against O’Toole being able to bed three of the day’s most famous blondes. O’Toole loved these kind of wagers, and he took it very seriously.
35. The Odd Were In His Favor
The three best known blondes of that time were Anita Ekberg, Jayne Mansfield, and Diana Dors—all celebrities and all gorgeous. Darwin Porter and Danforth Prince, authors of an O’Toole biography, say that O’Toole methodically set out to win the bet and, according to the authors, he walked away with the winnings. O’Toole was a regular Casanova, but was he enough of one to arouse a Princess?
36. He Lived A Fairy Tale
O’Toole met Queen Elizabeth’s sister, Princess Margaret, in 1965. It took a while, but eventually the two lovebirds canoodled in the same bedroom where Winston Churchill slept when he was meeting with president Roosevelt. I’m surprised that fact alone wasn’t a buzzkill. Apparently, the affair continued on for eight long years. And all this, while he was still married to Phillips.
But his infidelity definitely didn’t end there.
37. He Played A Dangerous Game
O’Toole also had a long affair with Elizabeth Taylor—and was also a drinking buddy to her husband Richard Burton. In 1964, O’Toole and Burton were on a film shoot together, and O’Toole wanted to rub his affair in Burton’s face. To do this, O’Toole snuck an undressed Taylor onto the set and hid her under a blanket until the cameras rolled. The gag was meant to surprise Burton, but ended up infuriating him instead.
38. He Received Some Corporal Punishment
O’Toole also ruffled Katharine Hepburn‘s feathers. She called him “Pigs” because of his behavior, and he called her “Nags” because she complained about it. On the set for 1968’s The Lion in Winter, Hepburn berated O’Toole for keeping her waiting on set. When that didn’t work she went one step further: She punched him in the face. Sadly, O’Toole’s behavior didn’t improve on his next film.
39. He Wasn’t Supportive
O’Toole’s behavior with his wife on 1969’s Good-bye, Mr. Chips set was deplorable. He flatly refused to rehearse with his wife, and weirdly kept his distance from her. But the insults didn’t end there. Once, when a reporter asked Phillips how she combined private life and career, O’Toole chimed in with a rude interjection: “She doesn’t have a career—she just has jobs.”
40. He Was Too Dramatic
Even though O’Toole criticized his wife’s career, his own career hit a considerable rough patch. He seemed to be appearing in flop after flop. The poor guy couldn’t get a break, and some critics thought it might be because his melodramatic acting style was going out of fashion. Certainly his constant drinking wasn’t helping either.
41. He Lost His Buddy
Even though O’Toole had a decades long ongoing fling with Elizabeth Taylor, it didn’t stop him from going drinking with her husband Richard Burton. But the two boozers’ antics went too far when Taylor found them inebriated, and singing Happy Birthday to each other while sharing a rather long hug. At her wit’s end, she forbade Burton from drinking with O’Toole. Surprisingly, Burton obeyed. Their fun had officially come to an end. It was time for O’Toole to find his next next plaything.
42. He Started A Battle
In 1975, O’Toole was on location in Mexico filming Man Friday—yet another movie that failed to excite critics. Although audiences didn’t love it, O’Toole himself had quite a romp while filming it. His stunning Mexican costar, Malinche Verdugo certainly captured his attention, and soon, their spark of attraction turned into a full-blown affair.
However, it wasn’t long before O’Toole’s wife caught wind of his infidelity, and this time, she refused to turn a blind eye.
43. He Got A Taste Of His Own Medicine
Caught red-handed once again, O’Toole broke Phillips’ heart. Increasingly unhappy with her marriage, she threw caution to the wind and devised a plan for revenge. While appearing in a West End play, she grabbed the nearest warm body, and used it to betray her husband. The warm body was costar Robin Sachs, who was 17 years younger than her.
But unlike O’Toole’s meaningless flings, Phillips later married Sachs for a second shot at the “happily ever after” O’Toole never gave her.
44. He Lived A Lie
O’Toole and Philips continued to live as husband and wife, and both of them conducted affairs on the side. But Phillips was new to the game of adultery, and eventually spilled the beans to O’Toole. At first nothing happened, but then the arguments started. By 1979, Phillips had had enough of their heated marriage and moved out. She did, however, forget one or two important things.
45. He Kept The Kids
When Phillips left O’Toole, it’s likely she thought it was a temporary separation. She decided to leave the kids with her husband. Phillips’ mother, Mamgu, was living there at the time, and they were used to having her as a caregiver. Phillips was just trying to keep some normalcy to the kids’ lives. But what happened next was anything but normal.
46. He Replaced Their Mother
After his wife’s departure, it wasn’t long before O’Toole invited his mistress, Malinche Verdugo, into the family home. He then went to work on Phillips’ mother. Mamgu had grown quite fond of O’Toole (even though he’d once called her an“old Welsh cow”), and O’Toole wanted Mamgu to live with him and his new partner; he wanted her to help raise the kids. It was a difficult decision for Mamgu—or at least, it should’ve been.
47. His Charms Knew No Bounds
When it came down to it, Phillips’ mother adored O’Toole, and she completely took his side. But it was even worse than that. Over lunch one day, Mamgu told her daughter that she’d decided to look after Verdugo like she was her own daughter. But as mind-boggling as her mother’s betrayal was, Phillips had another thing coming when it came to her ex-husband.
O’Toole didn’t take kindly to being left, and he never let her forget it.
48. He Erased His Wife
O’Toole wasted no time in removing Phillips from his life. He closed their joint bank account, he stopped her allowance, and ended her medical insurance. As far as the house went, he bought her out—which was the only money Phillips got from the deal. He made it his mission to erase her from his life; the cut was mercilessly clean and utterly final. And O’Toole? He was ready to move on.
49. He Took A Pay Cut
O’Toole had already made a fortune in films, and yet there was something on his bucket list that money couldn’t buy. He wanted to appear on stage as MacBeth. He eventually fulfilled his dream in 1980, and got paid only $500 a week to do it—that’s the equivalent of $1,600 a week in today’s money. O’Toole put his heart and soul into playing Macbeth, but, sadly, the critics didn’t seem to care. To his dismay, O’Toole received some of the worst reviews in his lifetime.
50. He Found A Model Wife
After briefly dating Trudie Styler—who went on to marry Sting—O’Toole started dating model Karen Brown, who was 15 years younger than him. In 1983, they had a son, Lorcan. Eventually O’Toole and Brown parted ways and, in true O’Toole fashion, he somehow managed to take Lorcan with him. Lorcan, O’Toole’s only son, would later turn to acting, and appear in TV’s Sons of Anarchy.
51. He Had His Eye On The Prize
In his lifetime, O’Toole received eight Academy Award nominations, and never won a single one. He’d received all kinds of other honors including BAFTAs, Golden Globes, and Emmys, but never the elusive Oscar. In 2003, the Academy offered him a lifetime Achievement Oscar. Finally, O’Toole was going to get what he’d always wanted. So, why was his reaction so bizarre?
52. He Won The Award Of A Lifetime
O’Toole told the Academy to “get lost.” He regarded the Lifetime Achievement Award as second place, and didn’t want it. He eventually came around, and ended up accepting it from Meryl Streep. Before the ceremony, O’Toole almost stormed out because there was a no drinking policy. They made an exception, and he shared a sip or two backstage with Streep before accepting his award.
53. He Battled Many Illnesses
Over the years, O’Toole had faced many health crises. He’d had his pancreas and some of his stomach removed because of cancer, and as a result, he developed diabetes. He spent the final years of his life somewhat reclusively, sometimes spouting Shakespeare’s sonnets—he’d memorized all 154 of them. When his stomach cancer returned in 2013, it was the end for him.
54. He Kept A Promise
Back when O’Toole was 18 years old, he was already planning his career as an actor. He had a notebook, as many young artists do, and in it he wrote himself a promise: “I will not be a common man. I will stir the smooth sands of monotony. I do not crave security. I wish to hazard my soul to opportunity.” I would venture a guess that O’Toole remembered this promise every day of his life.