Scandalous Facts About Carly Simon, Pop’s Most Passionate Woman

December 8, 2023 | Erica Ball

Scandalous Facts About Carly Simon, Pop’s Most Passionate Woman

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”.

Singer-songwriter Carly Simon photographed in June 1971Jack Mitchell, Getty Images

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.

Musician Carly Simon and mother Andrea SimonRon Galella, Ltd. , Getty Images

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.

Publicity photo of Carly Simon published by her record labelElektra, Wikimedia Commons

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. 

Daniel CraigEON, From Russia with Love(1963)

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. 

Carly Simon in 1974 press photoElektra Records, Wikimedia Commons

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. 

Carly Simon publicity headshot from Elektra RecordsElektra/Pam Frank, Wikimedia Commons

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.

Gina Lollobrigida  Sean ConneryUnited Artists, Woman of Straw (1964)

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.

Press photo of Carly Simon, 1972Unknown Author, Wikimedia Commons

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.

Photo of Lucy Simon (left) and Carly Simon of The Simon Sisters posed circa 1965GAB Archive, Getty Images

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.

Carly Simon (1971)Unknown Author, Wikimedia Commons

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.

Jack Nicholson factsHerbert Dorfman, Getty Images

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.

Carly SimonMichael Putland, Getty Images

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.

Photo of Cat Stevens on stageMichael Ochs Archives, Getty Images

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.

Photo of Carly SIMONRB, Getty Images

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.

Singer Carly Simon sitting at homeWWD, Getty Images

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.

Warren BeattyUnknown Author, Wikimedia Commons

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.

Warren Beatty and Natalie WoodFilm Star Vintage, Flickr

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.

Photo of Carly SIMONGems, Getty Images

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. 

Jack Nicholson And Warren Beatty During Filming Of The Motion Picture  The Fortune,  In Los Angeles, Calif., 1974Larry Bessel, CC BY 4.0 ,Wikimedia Commons

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. 

Warren BeattyJohn Irving, Flickr

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.

Carly Simon in whiteRon Galella, Getty Images

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.

Carly Simon, portrait, London, 1972.Michael Putland, Getty Images

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.

Marvin GayeJim Britt, Wikimedia Commons

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. 

James Taylor and Carly Simon, 1975Kathleen Ballard, Wikimedia Commons

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. 

Singer James Taylor poses with wife singer Carly Simon at the Waldorf Astoria Hotel.Bettmann, Getty Images

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. 

Carly Simon and James Taylor Arriving at PartyBettmann, Getty Images

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.

Mick Jagger performingBert Verhoeff, CC0, Wikimedia Commons

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.

Torino, 1982, Mick Jagger performingGorup de Besanez, CC BY-SA 3.0 , Wikimedia Commons

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.

Carly Simon On StageMichael Putland, Getty Images

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. 

Carly SimonKathy Hutchins, Shutterstock

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.

Mick Jagger and Marianne FaithfullBen Merk, CC0, Wikimedia Commons

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!” 

American actor Warren Beatty poses in the 1960's.Archive Photos, Getty Images

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. 

Mick Jagger and Keith Richards performing as The Rolling StonesFairchild Archive, Getty Images

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. 

Singers Carly Simon and James Taylor and Senator Ted KennedyRon Galella, Getty Images

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.

Carly Simon and James Taylor singingArthur D'Amario III, Shutterstock

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.

Carly Simon performs on stageMichael Putland, Getty Images

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. 

Carly Simon Performs at GardenState Arts Center 1995L. Busacca, Getty Images

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. 

Carly Simon recordPiano Piano, Flickr

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. 

Carly SimonLynn Goldsmith, Getty Images

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. 

Carly SimonL. Busacca, Getty Images

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. 

Carly Simon Performs In Grand Central StationGene Shaw, Getty Images

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.

Carly Simon in stripped topAlan Light, CC BY 2.0, Wikimedia Commons

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. 

John F. Kennedy, Jr. FactsEvening Standard, Getty Images

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. 

Carly SimonDebra L Rothenberg, Getty Images

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.

Carly Simon, James Taylor, Ben Taylor, and Sally Taylor Walking Outside 135 Central Park West, Carly Simon's ApartmentRon Galella, Gety Images

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. 

Donald Trump wearing a suit is pointing at front.Gage Skidmore, Flickr

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. 

Musician Carly Simon and sisters Lucy Simon and Joanna SimonRon Galella, Getty Images

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.

Carly Simon and Ben Taylor attend Glamour Magazine celebratesPatrick McMullan, Getty Images

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.

Carly Simon and Ben Taylor attend Glamour Magazine celebratesPatrick McMullan, Getty Images

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".

Taylor Swift attends the InStyle And Warner Bros. Golden Globes After Party at The Beverly Hilton Hotel in Beverly HillsRich Fury, Getty Images

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