Sir Laurence Olivier was a figure like no other. People often refer to him as the greatest actor of his generation—if not of all time—but behind the scenes, he struggled desperately with painful secrets that followed him throughout his life, all the way to his tragic end.
1. He Eschewed The Family Tradition
While Laurence Olivier grew up to be a dazzling stage presence, he came from a long line of clergyman—but he wasn’t as much of an odd duck in his family as you might think. His father Gerard always had a flair for the dramatic and considered a career as a stage actor before trying his hand at teaching and then, eventually, becoming a priest in the Anglican church.
The church was a huge part of Laurence’s life as a child as well—but not for the reasons you’d expect.
2. He Saw What He Wanted To Do
Each week as his father lead his congregation in church, Laurence sat there, quietly absorbing it all…but he wasn’t interested in the substance of the worship. What interested him was the style—his father’s performance. Gerard would go from quiet reverence to booming admonition, even slipping in a joke in between, with the greatest of ease.
Laurence wanted to do the same thing, albeit in a different venue. But that doesn’t mean that he necessarily got along with his father.
3. They Had An Icy Relationship
Laurence’s father Gerard was a bit unconventional in his beliefs, and as a result, he had trouble finding a permanent posting that would provide a steady home and routine for his family. While he was close with his mother, Laurence felt that there was a cold distance between him and his father—and the reason why was heartbreaking.
Laurence believed that since he already had an older brother and sister, his father thought of him as needless—nothing but an extra mouth to feed. On top of that, Gerard had a fiery temper that terrified Laurence and his siblings.
Laurence began to look for a way out, and before long, he found one.
4. His Whole Life Changed
Laurence wasn’t a star pupil, but he did gain admission to the All Saints choir school, where he began to find his own voice and perform in productions of Shakespeare plays. Students at the school went home one weekend a month, and on one of Laurence’s trips home in 1920, he got devastating news. After a period of ill health, doctors had discovered that his mother Agnes was suffering from a brain tumor.
That March, during Laurence’s visit home, Agnes pulled him close and whispered “Goodbye, my darling”. He returned to school—not knowing that it would be the last time he ever saw her.
5. He Lost His Biggest Ally
For years, Agnes had made up for her husband’s cruel attitude to his youngest son by doting on Laurence and making him the clear favorite of the family in her eyes. Sadly, just two weeks after she’d said her sweet words of farewell to her son, Agnes died. Laurence was only 12 years old, and the loss was earth-shattering.
He found some comfort spending time with less dysfunctional branches of the family—but at school, where he spent most of his time, there was little reprieve.
6. His School Was A Hotbed For Debauchery
Laurence graduated from All Saints and began attending St.
Edward’s School, where he focused on school plays to the detriment of pretty much everything else, including his classes. But there were also other, much more scandalous sources of distraction. Laurence was underweight, delicate, and often took on the female parts in plays, which meant that he was very popular with the other boys.
These types of inappropriate shenanigans weren’t uncommon in boys’ schools at the time and Olivier freely admitted to them later in life—but, as we’ll see, that didn’t mean he was always so open with his private life…
7. His Father Told Him Exactly What To Do
Despite his stage successes at school, Laurence Olivier still had no idea what he was going to do for money when he graduated—and he had to think quick. His older brother had gone to India to strike out on his own, and Laurence considered following him.
Yet when he told his father about it, he was in for a surprise. Gerard Olivier told his son he wouldn’t be going to India, and that he was instead destined for the stage.
And that wasn’t all—Gerard had a plan, too.
8. He Followed In His Sister’s Footsteps
Laurence’s older sister Sybille was already a student at the Central School of Speech Training and Dramatic Art. That was where Gerard wanted Laurence to go…but there was one caveat.
He was cutting his son off, and expected him to get by on a scholarship. Luckily for Laurence, the school was desperate for male students, and everything went according to plan.
When school wasn’t in session, he acted with touring companies—and it was on one of these sojourns that his life changed completely.
9. He Fell In Love
Laurence Olivier had barely a penny to his name and, according to basically everyone he met back then, he definitely looked the part of the starving artist. Unfortunately, this all worked against him in the romantic department.
Still, when he met actress Jill Esmond, the daughter of two famous actors, he was determined to get her to see past his bedraggled façade.
While she liked him, she didn’t exactly make it easy for him…
10. He Made A Drastic Decision
Olivier fell for Esmond when they appeared in a play together.
In the third week of the production, he proposed. Her reaction was brutal. Not only did she say no, but he found out that she was also taking off for a part on Broadway. Still, Olivier wasn’t going to let a little thing like the Atlantic Ocean get between them. He followed her to New York.
Olivier was there to build his career—but he also had other motives.
11. She Had Reservations
At this point, Laurence Olivier was 21 years old and his only experience in the bedroom had been with other boys at school.
He was absolutely desperate to get married and see what the fairer sex had to offer, so his campaign to convince Esmond to be his wife continued in New York. While she accepted a ring from him, she continued to say how unsure she was about the whole “marriage” thing.
Was this a terrible omen?
12. He Had To Take Care Of His Sister
When Olivier returned to England to wait for Esmond to finish her run in the States, he made a disturbing discovery. His sister Sybille was both a newlywed and a new mother—and it appeared she was losing her mind. She’d have frequent screaming fits and had even tried to give the baby to a group of nuns. Olivier helped to have her committed.
The experience was horrible—and his “fiancee’s” reaction was even worse.
13. She Changed Her Mind
When Esmond wrote back to Olivier after he broke the news about his sister, she told him that it was his problem, not hers.
Ouch. Still, she wasn’t entirely without compassion. After a lonely December in the US, she tearfully told Olivier over a long-distance call in the wee hours of the New Year that she was coming back to him.
Did she get totally sidetracked by a sunny vacation on the way home? Yes. But she also, eventually, kept her promise to him.
14. Their Honeymoon Period Was Short
Finally, in June of 1930, Laurence Olivier and Jill Esmond tied the knot.
After the struggle that preceded it—nearly two years apart, family and money troubles—it seemed like a fairy tale. In reality, it was more of a nightmare. It took mere weeks for them to realize they’d made a terrible mistake, but by then, it was too late.
Following the tradition of many men before and after him, Olivier hid from the sad reality of his broken relationship by throwing himself into work.
15. He Met His Mentor
At the time, Noel Coward was one of the hottest playwrights—and social figures—in London. When he caught Laurence Olivier on stage, he was blown away by the actor’s talent and cast him in his play Private Lives. It was a smashing success, and became Olivier’s big break. On top of that, Coward became both a close friend and a mentor to Olivier.
When the time came to take the play to New York, they needed to find a new leading lady, so they made the convenient choice to take Esmond with them. However, it wasn’t all smooth sailing for the three.
16. The Tables Turned On Him
In London, critics had lauded Olivier as the next big thing.
Well, in the US, they only had eyes for his wife. While they were both doing screen tests, Esmond was the one with the big offers from film studios, and these were offers she couldn’t refuse. In England she was making £8 a week, but Fox Studios in Hollywood wanted to pay her $875 a week for a year.
She didn’t want to go, but when Olivier finally netted a similar offer, she made the decision for both of them. A year in Hollywood to make bank, and then they could move on with their lives.
But you know what they say about the best-laid plans…
17. They Became Instant A-Listers
When they arrived in Los Angeles, Laurence Olivier and Jill Esmond immediately found themselves at the center of the Hollywood scene. They hob-knobbed with stars like Joan Crawford and Douglas Fairbanks Jr. But their social successes didn’t translate into film success, and with a few flops under his belt, Olivier headed back to the comfort of the London stage.
However, Olivier was nothing if not tenacious, and the failure stung.
He wasn’t ready to entirely give up yet.
18. He Got Brutally Rejected
Hollywood came calling again with one of the most desirable parts going. They needed a male lead to star opposite Greta Garbo, one of their biggest stars, in Queen Christina. Olivier seemed perfect for the part, and he dutifully showed up to set to face Garbo—only to make an upsetting discovery. For all their talent, Olivier and Garbo had no spark.
Within weeks, it became clear that the lack of chemistry would ruin the film, and Garbo insisted on replacing Olivier with her ex, John Gilbert. It was the right decision for the movie, but Olivier returned to the UK once more with his tail between his legs and a new plan.
19. He Was A Busy Man
Laurence Olivier went back to what he knew best—Shakespeare performances on the London stage. And it was good timing too, as Esmond got pregnant in late 1935. Despite his busy schedule and the looming prospect of fatherhood, Olivier still found time to keep a dirty little secret from Esmond.
He had a brief affair with actress Ann Todd.
This relationship ended as quickly as it began—but he wasn’t the only one with a wandering eye.
20. She Cheated On Him
Garbo’s rejection of Olivier for Queen Christina had been soul-crushing—but when he went back to his wife, he experienced a much more bitter rejection. Not only had Esmond lost her interest in him, but she’d also begun to sleep with other women behind his back. Olivier, again, threw himself into his career.
When Esmond got pregnant, he hoped they could turn it around.
But even after she gave birth to their son, it was clear that perhaps too much damage had been done for them to fix things.
21. He Fell In Love
Olivier worked at breakneck speed, appearing in countless Shakespeare productions and learning over 12,000 of the Bard’s lines over the course of a year or so. One day after a production of Romeo & Juliet, he got a hard lesson on the meaning of the term “star-crossed”. Actress Vivien Leigh, then still a fledgling star, approached him at a restaurant and congratulated him on his performance.
Her beauty and poise enchanted him—and now, much as it had nearly a decade before when he met Esmond, his obsessive side came out.
22. They Had A Behind-The-Scenes Romance
Olivier said that when it came to Leigh, he couldn’t help himself, and he immediately pursued her. But there was just one problem. She was also married.
But Leigh was no stranger to infidelity either, and she soon began a passionate affair with Olivier. The fact that they’d been cast opposite each other in a film called Fire Over England gave them further pretense to continue the tryst.
When the filming ended, they expected to part ways.
Only, Olivier couldn’t let go.
23. He Got Cold Feet
In 1937, Olivier received an invite to play Hamlet at Elsinore, the Danish castle where the play is set—quite the distinct honor. He slyly suggested that the producers cast Leigh as Ophelia.
Before they’d even left for Denmark, Olivier had made a drastic decision. He wanted to tell his wife that it was over and that he was leaving her for Leigh. But then, he choked.
24. She Scared Him
One day during rehearsals for Hamlet in Elsinore, Leigh began to exhibit strange behavior. She started screaming at Olivier before going silent. The show went on as planned, and the next day, when Olivier asked her about it, she couldn’t remember a thing. It was jarring—and sadly, as we’ll see, a dark omen of what was to come for the couple.
25. They Finally Pulled The Trigger
Olivier and Leigh set off for their blockbuster performance in Denmark…with Jill Esmond in tow. They were in their element, and Esmond had no choice but the watch from the sidelines.
By the time the performance concluded, the truth of the matter was clear. When they returned home, both Olivier and Leigh respectively told their spouses that they were leaving them—but their plan didn’t exactly go off without a hitch.
26. They Got A No
Despite Esmond’s own issues within the marriage, when Olivier asked her for a divorce, she refused. Leigh faced the same problem, but despite all that, they forged ahead and began to live together—a move that the film studios had to work overtime to cover up. When Olivier went back to Hollywood to star as Heathcliff in Wuthering Heights, Leigh had her eyes on another great romance.
27. They Each Got Parts In Two Iconic Romances
The casting of Gone With the Wind was one of the hottest topics in Hollywood, and many people thought that Olivier had a chance to get the role of Rhett Butler—but they were in for a surprise. While Olivier toiled on the set of Wuthering Heights, Leigh campaigned so that she would get cast in Gone With the Wind. Her gambit worked—but Olivier had his own trials and tribulations to battle.
28. He Lost His Dad
As happy for Leigh as he was, Olivier had no interest in hanging around Hollywood and waiting for another part after finishing Wuthering Heights. He went back to the stage while his paramour made Gone With the Wind. While they were separated, he received heartbreaking news. His father had died suddenly of a stroke.
Even worse, Olivier was stuck in Indianapolis and there was no way he’d make it home for the funeral. He was bereft—but soon after the loss came a touching gesture.
29. She Came Through For Him
Olivier’s stepmother wrote to him that his estranged wife, Jill Esmond, had not only come to the funeral to stand in for him, but had also said that she’d finally begin divorce proceedings. It soothed his mind and his guilt over missing the funeral—but only for a little while. Sadly, trouble was on the horizon.
30. He Nearly Lost Her
While they were separated, Olivier and Leigh frequently called and wrote to each other. Yet while his letters were fervent (and occasionally explicit) declarations of his desire, her phone calls were occasions for her to express her jealousy.
They couldn’t always work it out over the course of one call. One night, she gave him the scare of a lifetime.
After hanging up, Leigh accidentally overdosed on sleeping pills. Her maid was able to revive her after a lot of panic, including a 4 am phone call to Olivier.
Leigh later apologized, but she was fragile, and both the distance and her long days on Gone With the Wind were making that seriously apparent.
31. He Wanted To Work With Her
The separation was wearing thin on both Olivier and Leigh, and his idea of a solution could’ve actually ruined his career if he’d had his way. He was due to star in Rebecca and Pride and Prejudice in quick succession, and in each case, he pushed to have Leigh cast opposite him. The studios outright rejected the idea.
After all, they were both still married to other people, and it was a bad look.
While he might not have gotten that wish, he at least had another come true soon after…
32. They Made It Official
Finally, in 1940, both Jill Esmond and Vivien Leigh’s first husband agreed to divorces, leaving Olivier and Leigh free to tie the knot. That August, they exchanged rings at San Ysidro Ranch in Santa Barbara, finally making their nearly three-year-long affair legit.
With their newfound freedom, they jumped into acting projects together—but things didn’t always go according to plan.
33. He Wanted To Help His Country
As WWII escalated and things got bad back home, Laurence Olivier felt called to help in some way.
The men in charge were encouraging English actors to stay in Hollywood and make pictures that would portray Britain positively, so Olivier and Leigh got together with director Alexander Korda to make That Hamilton Woman.
It was their first film together since their marriage.
It didn’t go well.
34. They Were Sick Of Each Other
The film’s tagline was “The Year’s Most Exciting Team Of Screen Lovers”—but behind the scenes, the cracks were starting to show. Their mutual obsession with each other had been fine when it took place in passion-filled letters, but in real life, Olivier soon grew tired of it.
To cope, Leigh began to drink heavily on set.
Their own personal war effort had led to quite a few battles between them, but regardless, they planned to go home and see what else they could do to boost national morale.
35. He Was A Fly Boy
Olivier and Leigh always had big ideas, but the follow-through didn’t always work out in their favor. Olivier planned to join the Royal Air Force while Leigh wanted to work as a nurse in Egypt.
Were either equipped for these respective jobs? Absolutely not. Still, while in the US, Olivier had worked hard to accumulate the 250 flying hours that would qualify him to be a pilot.
In the end, he joined the Fleet Air Arm with his friend Ralph Richardson…where they quickly gained quite a reputation.
36. He Wasn’t Talented As A Pilot
Richardson had already crashed his fair share of planes by the time Olivier joined him in the Fleet. Not one to be outdone, Olivier raced to catch up. Quickly realizing that Olivier’s service could best be used in a sector where he wasn’t destroying expensive aircraft, the powers that be encouraged him to make speeches and appear in propaganda films instead.
It was a responsibility that he, thankfully, took to very quickly.
37. They Didn’t Want Him
Olivier’s friend Ralph Richardson wanted to keep the Old Vic theater going during WWII as a means to boost morale and promote English culture, and he suggested Olivier as a co-director. When the theater’s governors asked the Royal Navy to release the two actors from duty, they were all too happy to let them go. Olivier even called their enthusiasm “positively hurtful”.
But, all in all, that sting didn’t last too long.
38. They Knighted Him
Olivier may have been unceremoniously dumped by the Navy, but in his fourth year at the Old Vic, he got an honor that made up for everything that had come before it.
In 1947, King George VI knighted Olivier for his contributions to stage and screen—making him the youngest actor to receive the honor. On top of that, Olivier directed and starred in a film adaptation of Hamlet, which went on to win the Best Picture and Best Actor Oscars.
The year was definitely a career highlight—but the highest highs can sadly sometimes precede the lowest lows.
39. She Cheated On Him
Olivier took Leigh and the Old Vic company on a six-month tour of Australia and New Zealand in 1948.
The grueling tour strained their marriage, and as Olivier later put it, he “lost Vivien” in Australia. And there was a more scandalous reason behind their divide. While they were there, Leigh began an affair with actor Peter Finch, and it wasn’t just a simple fling.
Olivier seemed to be none the wiser—but was he digging his own grave?
40. He Fooled Around With Her Co-Star
To add insult to injury, Olivier actually hired Finch for his production company and gave him a generous contract—all the while Finch was sleeping with his wife behind his back. With that said, the betrayal wasn’t one-sided. During the filming of A Streetcar Named Desire, which starred Leigh and Marlon Brando, one of Olivier’s friends remembered coming out to the pool and catching him in an embrace…with Brando.
It wasn’t the first time Olivier had an affair with another man—and it definitely wouldn’t be the last.
41. She Was Suffering
Both Olivier and Leigh’s careers flourished, but behind the scenes, each was fighting a private battle. Leigh’s seemed to be with herself, while Olivier struggled to know what to do as she got into more and more agitated states. Finally, they saw a doctor who helped them solve the mystery of what was happening to Leigh.
She was suffering from manic depression (now called bipolar disorder).
While it was comforting to know the root of Leigh’s extreme mood swings, it didn’t help fix them—and as time wore on, everything got worse.
42. She Wanted Out
Leigh did her best to hide her problems while making films—meaning that Olivier was really the only one who saw her at her worst. In 1953, she made a movie abroad with Peter Finch, and when she came back, she made a stunning declaration. Leigh told Olivier that she was in love with Finch and wanted a divorce.
This revelation was just part of a larger breakdown.
As Leigh’s mental health declined, the affair with Finch fizzled out. Sadly, even that couldn’t fix her marriage with Olivier.
43. He Put Her Away
By this point, Leigh was completely out of her mind.
She would scream for hours in her dressing room until doctors had to eventually sedate her. Olivier felt that he only had one option left. Like with his sister, he placed Leigh in an asylum for three months, where she endured multiple painful sessions of electroshock therapy.
44. They Fought Publicly
Leigh and Olivier’s marriage had been through the ringer at this point. They managed to weather Leigh’s affair with Finch, but their time was coming to an end. Audience members could hear the actors cruelly taunting each other during performances.
Off stage, Leigh made matters worse by fixating on scathing reviews that accused Olivier of underplaying his roles so that he wouldn’t outshine his less talented wife.
Olivier tried to convince Leigh that it wasn’t true, but the damage was done.
Still, even after all they’d been through, they still had one glimmer of hope.
45. They Had One Final Heartbreak
In 1956, 44-year-old Vivien Leigh miraculously became pregnant with Olivier’s child. The unlikely mother hoped that the baby could give her and Olivier a fresh start, but fate had other plans in store for the couple.
Leigh had a miscarriage and fell into a horrible depressive spiral and a breakdown filled with public outbursts.
When Leigh wasn’t stripping naked in a public park, she was trying to beat Olivier with a towel. Things were out of control, and there was nothing Olivier could do to make them better.
46. He Couldn’t Take It Anymore
Often, affairs are passionate, turbulent things—but Olivier’s marriage was already filled with instability, so when he strayed from Leigh, he sought out a relationship that was much more solid and easy. He found it with actress Joan Plowright—but there was a sick twist to their union. Not only was she 22 years younger, but they had also met while she was playing his daughter on stage.
Despite her fragile state, Leigh wasn’t about to take it sitting down.
47. Their End Was Dramatic
As their marriage went through its final death throes, Leigh threatened to take her own life if Olivier left her. Still, he was determined to get out while he could.
When the news broke about the impending divorce, Leigh went one step further to punish him and told the press about the other woman. It wasn’t a completely cold split, though, and Olivier continued to write Leigh letters after their divorce.
48. He Became A Father And Husband Again
With the paperwork filed, Olivier was free to tie the knot with Plowright—and they dove right into married life with the speed and skill of Olympians. Nine months after their wedding, Plowright gave birth to a son, and then two daughters in quick succession.
It looked like Olivier was finally having the kind of stable family life he’d never been able to achieve before.
49. His Health Declined
With personal success came even more professional triumphs, as Olivier helped develop the National Theatre and ran the Chichester Festival, where he directed icons like Peter O’Toole, Maggie Smith, and Anthony Hopkins. But then, right as he was in the middle of a run of stage successes, disaster struck. Doctors diagnosed Olivier with prostate cancer.
While they were able to treat him for it, it was the first of many in a long line of illnesses that he began to suffer toward the end of the 60s.
50. He Saw Her One Last Time
Olivier’s pains weren’t just physical, either. In July of 1967, Leigh died after a battle with tuberculosis.
Her partner John Merivale discovered her body—and the first person he called was Laurence Olivier. Even though they’d broken up seven years earlier, the acclaimed actor rushed to see her one last time. He insisted on staying with her body until the authorities removed it.
After that, Olivier helped Merivale organize Leigh’s funeral and arranged for Leigh to be cremated, with her ashes spread near her beloved home in East Sussex.
51. They Dumped Him
Try as he might, Olivier couldn’t leave the stage, and he stayed on as director of the National Theatre longer than he intended to—only to be met with a brutal blow. After years of service, the board unceremoniously ousted him.
Olivier was already a legend at this point, but with a growing number of ailments and three young children to support, he still had a lot to worry about when it came to the future.
52. He Struggled—But Made A Comeback
In his final years, Olivier took on roles that he might have scoffed at in the decades before, including a series of Polaroid ads and some cameos in lesser-quality films. Still, very little could keep Laurence Olivier down, and when his health allowed it, he could still lock down Oscar nominations even after he hit the age of 70.
53. The World Lost An Icon
Olivier fought through 22 long years of illness, acting as much as he could when his health allowed him. Finally, in 1989, Olivier died of kidney failure at the age of 82. Many of his contemporaries and critics agree that he was the greatest actor of his generation—if not all time. But when you’re that much of a legend, the story rarely ends at death…
54. They Thought They Were Lovers
For years, friends, fans, and biographers alike speculated about Olivier’s sexuality. After all, he was always quite open about his experiences with men.
In his biography, Olivier wrote a passage about being tempted by another man, and many believed he was talking about his old friend, Noel Coward—but Olivier’s own letters later revealed the truth.
55. He Had An Affair With Another Man
A series of letters between Olivier and fellow Shakespearean actor Henry Ainley seem to strongly hint that the pair had a passionate, if brief, affair in the mid-1930s, before Olivier took up with Vivien Leigh. They’re quite explicit, and Ainley mentions making Olivier’s first wife jealous in them. However, Ainley wasn’t the only one that Olivier had a fling with…
56. No One Knows What To Believe
One biographer believes that Olivier had a decade-long affair with comedian and actor Danny Kaye.
Friends like Noel Coward and Princess Marina seemed to confirm their romance…but other biographers deny that such an affair ever happened. Of course, when it comes to Olivier’s secrets, who better to ask than his third and final wife?
57. She Accepted Him
After Olivier’s passing, his official biographer finally asked Plowright, flat out, if he’d had affairs with men. Her reply?
“If he did, so what”? Sadly, she was alone in her acceptance of her late husband’s sexuality. Olivier’s son from his first marriage, Tarquin, did everything in his power to suppress any stories of same-sex dalliances.
Still, there was clearly one romance that haunted Olivier more than any other in his life…
58. They Always Remembered Each Other
In the weeks before Olivier’s own demise, he reportedly watched a movie that starred Leigh.
As he began to weep, Olivier simply said, “This, this was love”. Even though their relationship didn’t last forever, Leigh felt the same way about Olivier. The actress once said, “I would rather have lived a short life with Larry [Olivier] than face a long one without him”.