Long-haired and beautiful, singer-songwriter Carly Simon had a series of affairs that caught the attention of many. But behind the image of her laughing with the era’s heartthrobs was non-stop struggle and heartbreak.
1. She Was The It Girl Of The 70s
Carly Simon was raised by rich and musical, but dysfunctional, parents. They set her up well for her long music career, but also for a tendency to fall in love with the wrong kind of guy. Her list of lovers is a who's-who of the era's most captivating men, but also fodder for her musical hits, like “You’re So Vain”.
2. Her Parents Were Totally Dysfunctional
Simon’s parents were terrible role models. Her father was the co-founder of the book empire Simon & Schuster, but also depressed and distant, passing when she was just 16. Her mother had a history of scandalous relationships and carried on an open affair with the kids’ male nanny that their father turned a blind eye to. But that was just the tip of the iceberg.
3. She Had A Terrible Stutter
Simon’s home life was so stressful that when she was eight she developed a stutter. It worsened until she couldn’t even say “pass the butter” at the dinner table. However, her mother and speech therapist made a life-changing suggestion. They encouraged her to sing her words. It became a habit that would serve her well in the decades to come.
4. Sean Connery Wooed Her Aboard A Ship
Simon’s first liaison with a world-famous man was aboard a ship from England to New York in 1965. She and her sister and singing partner Lucy laid eyes on Sean Connery—and sent him a note inviting him to their cabin for tea or a cocktail. This daring act set off an evening to remember.
5. She Danced With Bond In The Presidential Suite
The handsome actor jumped at the chance to entertain the beautiful Simon sisters in the ship’s presidential suite, calling them within minutes of receiving their note. Champagne and dinner followed and Connery entertained the girls with his colorful stories. But, as it turned out, he had much more than just dinner on his mind.
6. She Turned Down 007
Connery’s real motivations for entertaining them in his lavish suite soon came to light. At a certain point, he decided it was time to all get up and dance. He gradually got close to them. He lavished them with compliments of their beauty and wit. He began to make comments about how they needed to make the most of their time together.
7. She Was Almost In A “Simon Sisters Sandwich”
Connery made it clear that although he was married, he was interested in sleeping with both of the sisters, or what Carly Simon called later a "Simon Sisters Sandwich". Simon did not take him up on the offer, and did not see him again after that night. Her sister, on the other hand, had a differing opinion—and the next day she made her move.
8. Her Sister Betrayed Her
Carly Simon took Lucy’s next actions as a betrayal.The night after they met Connery, Lucy did not return to their shared cabin at the end of the day. It became obvious that Lucy had taken up Connery on his offer and was spending the night. Simon slept alone in their room until Lucy made her way to her own bed well after 5 am.
But this wouldn't be her last scandalous interlude with a famous man.
9. She Was Part Of A Powerful Duo
They didn’t always agree, but Simon’s relationship with Lucy proved to be pivotal in both a professional and personal sense. Their folk music duo The Simon Sisters played regularly in Greenwich Village and brought them to the attention of the music industry. Simon could undoubtedly turn heads—and her conquests were legendary.
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10. She Had A Lot Of Famous Boyfriends
Carly Simon had her pick of men, and didn’t really have a type beyond that they were all creative. Many ended up being famous in their own right, like Michael Crichton, who wrote Jurassic Park, and film directors Bob Rafelson and Terrence Malick. But Simon had a soft spot for musicians and they formed her most lasting relationships.
Of course, she did have a brief and passionate fling with one of Hollywood's most infamous leading men.
11. She Did Like Actors Too, Though
Another man who won Carly Simon over was charismatic actor Jack Nicholson. Catching his eye at a party he’d attended with another girl, Simon brought him back to her place. At first, they just lounged together on her couch, sipping coffee. But it wasn't long before Nicholson made his move—and boy was it smooth.
12. She Drank Coffee In Bed
Carly Simon had a night of passion in store for her. Nicholson didn't waste much time before cheekily asking her, "Do you ever drink coffee in your bedroom?" Unfortunately, this short affair wasn't made to go the distance. Simon and Nicholson had only shared a few nights together before the actor began seeing someone new.
No matter, romance was definitely in the cards for Simon.
13. She Charmed Cat Stevens
Simon’s early lovers in the music industry included Cat Stevens, the famous singer-songwriter now known as Yusuf Islam. Simon was the opening act for Stevens when her debut album was just coming out. Despite being very nervous before the gig, Simon charmed him so much that they set up their first date. But it ended in disaster.
14. Cat Stevens Kept Her In “Anticipation”
On the night of their date, Stevens was very late. Simon’s frustration inspired her to write “Anticipation," one of her most popular and critically-acclaimed songs. She had cooked him “chicken with cherries in a cream sauce” and watched it go cold when the song came into her head almost fully formed. It was finished in minutes—but Simon didn't stop there.
15. Her Love Inspired Songs
During their seven-month relationship, Carly Simon wrote two songs for and about Stevens: “Anticipation” and “Legend in Your Time”. Stevens, for his part, immortalized their relationship with the song “Sweet Scarlet” after they broke up. They were excellent muses for one another, but for Simon, there was one muse that totally swept her off her feet.
16. He Was Brazen
One day, while Carly Simon was touring with Cat Stevens, a man entered her dressing room after only a quick knock. It was the infamous lothario Warren Beatty. Seeing her alone, and before even making introductions, he closed the door and came close—brazenly ogling her chest and asked, "Can I see you?" But his brazenness worked. As he knew it would.
17. She Appreciated His Moves
With his looks and charm, Warren Beatty won her over right away. He was, to Simon, a “glorious specimen of man” who knew how to woo any woman he wanted. One of his moves was to take out his list of women he called “the main loves” of his life that included Marie Curie and Catherine the Great and add his new lady to the top of it.
Beatty seeming like Prince Charming—but this romance would end with one unforgettable song.
18. She Saw Right Through Him
Carly Simon knew their time together was not going to last but she was still going to enjoy herself. What she might not have expected, though, was that she was still underestimating the man’s libido. Their time together would partly inspire Simon’s greatest hit, “You’re So Vain”. Though that confirmation would come decades later.
19. She Enjoyed Their Nights Together
Beatty was already well known as a ladies’ man, and it seems by the time he was with Simon he was able to rival the best movie love scenes. Simon would go on to say that it seemed he had “created a brand new manual on how to make love”. Unfortunately, she would soon find out she was not the only one enjoying his attention.
20. She Didn’t Know About The Other Woman
We know it occurred at least once that Beatty was with two women on the same night. The story goes that Beatty called Simon to say he would be in town soon and needed to see her, arriving at her place just after midnight but leaving by 5:30 am for a film shoot. Sometime either before or after, he made another stop.
21. Her Therapist Busted Beatty
In the end, Carly Simon found out about the other woman from the most unlikely source. The morning after her whirlwind night with Beatty, she was in an appointment with her therapist and told him what had happened when he suddenly looked pale. He was unable to keep to himself that he had already had a patient that morning with the same story.
Beatty's two-timing way had been exposed. Sadly, there was even more heartache in store for Simon.
22. She Dealt With Gross Stuff, Too
It might be tempting to believe Simon’s life at this time was a kaleidoscope of free love frivolities, but that wouldn't be the truth. Her looks and fame brought a fair amount of negative attention from men as well. Some, like Albert Grossman, propositioned her disrespectfully, others crossed the line in a more serious way.
23. She Won’t Keep Their Secrets
Carly Simon has been outspoken about men’s problematic behavior to her, like the time comedian Redd Foxx revealed himself to her in his dressing room, or the time Marvin Gaye forcibly kissed her. Like her previous experiences, Simon channeled her reactions to arrogant and entitled men into her songs. All this would come out in her biggest hit.
24. She Married Jamie From The Vineyard
Despite the whirlwind of romances she often found herself in, Carly Simon fell in love with someone she’d known since childhood. She and James Taylor had both spent summers with their families in Martha’s Vineyard. In 1971, Simon saw Taylor on the cover of Time magazine and declared to her sister that she intended to marry him.
She did, but it was far from the perfect picture.
25. She Called James Taylor Her Muse
It took Carly Simon a few months to track him down, but when he performed at Carnegie Hall, she approached him afterward. She was as smitten with him in person as she’d expected. Maybe more so. He became her muse, or "darling," and soon moved into her apartment. Everything felt right to her, but Taylor had more than his share of demons.
26. Her New Man Had A Secret
Carly Simon was head-over-heels for Taylor, but he was in the grips of a terrible addiction. In a desperate attempt to fight it, he brought it all out in the open to Simon before flushing it all down the toilet. Unfortunately, that was not the end of it. On top of this, there were other aspects of Taylor's behavior that were red flags.
27. She And Taylor Were Volatile
Taylors moods were unpredictable and when they turned sour he could become mean and biting. At such times, he would berate and yell at Simon and others, including their mutual friends like Joni Mitchell. But their relationship would withstand all this, as well as one of Simon’s most talked-about liaisons, with Mick Jagger.
28. She Turned Mick Jagger’s Head
Six months into living with Taylor, Simon met Mick Jagger, front man of The Rolling Stones, at an Atlantic Records party. The energy between them was palpable and the attraction was mutual. But since Simon was in a newly-committed relationship and Jagger was married at the time, nothing happened. At least not that night.
29. She Took All The Vain Men To Task
Soon after meeting Jagger, Simon wrote and recorded the song that would become her most enduring legacy: “You’re So Vain”. For decades after its release, fans tried to guess just who this blistering song was about. Possibilities included any man Simon had been linked to in the past and whole books were written about the puzzle.
30. She Milked The Mystery For Years
For her part, Simon enjoyed dropping little hints whenever it suited her, usually when she was promoting a new album. In 2003, the lucky bidder of a charity auction won the answer for £35,000, but was sworn to strict secrecy. It would be over a decade more before she would provide a more definitive answer.
31. She Teased Us With Hints
A year later, Simon dropped the most tantalizing clue, a few of the letters from the man’s name: E, A, and R. Fans were excited until they realized that still conveniently left what many considered to be the three top contenders, Mick Jagger, James Taylor, and Warren Beatty. Those with money on Beatty were on the right track.
32. She Finally Gives A Partial Answer
Finally, in 2015, Simon revealed that the second verse is indeed about Beatty, but not the rest. For his part, Beatty had assumed he was the inspiration, reportedly calling her up after its release to say, “Thanks for the song". Simon’s reaction is to paraphrase the song’s famous refrain: “Warren thinks the whole thing is about him!”
33. Recording “You’re So Vain” Was Electric
The recording of the song had become an event in itself when Simon’s producer invited Mick Jagger to join her. The 45-minute session was electric and they began spending more time together while he was recording his own songs as well as at the Portobello Hotel. Simon was still determined to marry Taylor, until they got a call from Jagger’s wife.
34. Bianca Jagger Was Jealous Of Her
Bianca Jagger called Taylor the night before their wedding to tell him about Simon’s and Jagger’s supposed affair. The connection was bad and Taylor couldn’t quite make out what she was saying, but he understood enough to counter that he trusted Simon and didn’t believe she’d been unfaithful. So the wedding went on as planned.
35. She Was In A Tumultuous Marriage For Years
Simon might have saved herself some heartache if she hadn't married Taylor. It wasn’t long before it became obvious that her husband still struggled with his addictions. He drank heavily every day. However, the pair stuck it out for years and even had a daughter together. Then, just as Simon was beginning to suspect she was pregnant again, Taylor made a shocking confession.
36. She Tried To Smash A Guitar On His Head
One day, Taylor cruelly revealed he’d had an affair by suggesting he need to get checked for an STI. It took a while for her to process that. Later that evening she suddenly got out of bed and tried to break a guitar over his head. The guitar was saved but her anger had not subsided. Yet even this didn’t break them up.
37. Her Marriage Got Messier And Messier
They stayed together, but their relationship became more and more strained. Years later, after learning about another affair, Simon decided to give him a taste of his own medicine—and began one of her own. When she told Taylor, it turned out it was worse than she thought. He wasn’t just seeing one woman, he was seeing several.
38. She Confronted His Mistress
One of these women was a dancer living in the apartment Taylor rehearsed in. Simon decided to take the bull by the horns. She went to the apartment and confronted her—but the mistress went on the offensive, insulting Simon’s appearance and declaring that Taylor no longer loved her. Simon ended up simply leaving, and both affairs continued.
39. She Had A Panic Attack On Stage
Just like when she was a child, the stress in Simon’s life took a physical toll on her. During the first song at a show one night Simon was struck by a massive panic attack. Her heart was hammering, and she had to stop singing and explain to the audience what was going on. The audience responded in a surprising and loving way.
40. Her Fans Came To Her Rescue
About 50 people ended up coming onto the stage to help Simon, but her palpitations kept getting worse and other physical symptoms began to appear. Somehow she was able to pull herself together enough to finish the show, though at the cost of a month’s stay in the hospital. After that month, Simon’s life would be forever changed.
41. She Went Home To An Empty House
During her month recovering in hospital, she was visited by both her husband and her boyfriend. But Taylor had already decided their marriage was over and had become seriously involved with another woman. By the time she left the hospital, her house was empty. Taylor would go on to remarry shortly after he and Simon divorced.
42. Her Career Rebounded In Her 40s
Despite the tumultuous years in her personal life, Simon’s career was about to rebound. Her next album had a number of hits and included the score for the film Working Girl, "Let the River Run". That song actually made Simon the first to win a Grammy, Oscar, and Golden Globe for a song composed, written, and performed by one artist.
43. She Turned Tragedy Into Music
Professional success was great, but tragedy came for Simon in an unexpected way. In 1994, she lost both her mother and her friend Jackie Onassis to cancer in the same year. As always, Simon turned to music to express her emotions and process her grief, writing “Like A River” for her mother and “Touched by the Sun” for Onassis.
44. She Survived Cancer
Just a couple of years later, Simon fought cancer herself, undergoing surgery and chemotherapy. Just as this was occurring though, she lost another famous friend, Linda McCartney, to the same condition. And that was not the last time cancer would take someone Simon loved. Next time, it hit even closer to home.
45. She Was Still Making Good Music
In the meantime, Simon’s career was back on track. She worked on different TV and movie scores and released critically and commercially successful albums. She even began touring with her two children. As well, she published her highly-anticipated memoir, detailing her personal life and early relationships, including the most scandalous ones.
46. She Used Her Songs For Social Change
In 2016, Simon went public with her political views for the very first time—and they truly rocked the boat. She allowed "You're So Vain" to be used in an attack ad against then-candidate Donald Trump who she had previously met and found "repulsive". The Access Hollywood tape had just been released and Simon had her own history of experiencing unwanted advances.
47. She Lost All Her Siblings
Simon has outlived all of her siblings. Her younger brother lost his battle with cancer in 2018. And then in 2022, Simon suffered the devastating loss of both her sisters to cancer one day apart. Of four siblings, she was the only one who survived the terrible condition. One can only imagine the strength needed to go on after losses like that.
48. She Missed Her Hall Of Fame Ceremony
Due to these devastating losses, Simon was unable to attend her own induction to the Rock and Roll Hall of Fame a month later. Fellow singer-songwriter Sara Bareilles read a note from her about how humbled and shocked she was, despite being "under-qualified". She is, to this day, one of only a small number of women to have been given the honor.
49. She Continues To Inspire
In addition to her countless fans and many awards, the strength and vulnerability in Simon’s songwriting has inspired countless musicians. Her songs have been covered by everyone from Marilyn Manson to the Foo Fighters, Celine Dion, and Radiohead. Many of today’s top stars credit Simon’s music for inspiring and shaping theirs.
50. She’s A Beacon For Female Artists
Her most enduring impact was in paving the way for female singer-songwriters. Taylor Swift, who brought Simon on stage to duet “You're So Vain” on the Red tour, has said she admires Simon’s honesty and strength. She's even gone so far as to say that "You're So Vain" is "the best song that's ever been written".