1. In 1991, about a year after Pretty Woman came out and made Julia Roberts just about the biggest movie star in the world, she was engaged to her Flatliners co-star Kiefer Sutherland. The two were planning a lavish Hollywood wedding, with hundreds of guests expected to attend. But then, just three days before the ceremony, Julia called the whole thing off. It was some serious, pre-internet-era drama that had people calling friends on the phone and going, “Did you see Entertainment Tonight?!” The drama was only starting, though, because on the day she was supposed to marry Kiefer, Julia was spotted spending time with Jason Patric, one of Kiefer’s friends and his costar in the 1987 vampire movie The Lost Boys. And then — rather than quietly going home to recover from the breakup — Julia and Jason traveled to Ireland together!
Naturally, the tabloids went absolutely nuts. British newspapers claimed Julia and Jason were kissing and holding hands at a hotel, and reported that Kiefer sent Julia a letter asking for forgiveness. Didn’t happen. Julia and Jason were beginning a relationship that would last for roughly a year.
So did Jason steal Julia from his pal Kiefer? We can’t say for sure, but according to People’s 1991 reporting, an eyewitness at a Tucson spa said they saw Julia and Jason there five days before the planned wedding. That seems pretty innocent to me, right? RIGHT?
In a later interview, Kiefer said he’d been surprised that Jason hadn’t contacted him directly about his romantic feelings for Julia. The two men went decades without seeing one another (reuniting for the first time in 2010). Then, in 2021, they appeared together on Michael Rosenbaum’s Inside of You podcast. Kiefer forgave Jason, saying, “That was a difficult time for me … but look, honestly, the truth where I’m coming from, you fall in love, you fall in love. There’s nothing you can do about that.”
2. Before Daniel Craig became James Bond, he was an up-and-coming actor who was friends with Jude Law. The men had known each other for years and even co-starred in Road to Perdition. But in 2005, their friendship hit a serious rough patch. At the time, Jude was engaged to model-turned-actor Sienna Miller, but their romance was not in a good place (understandably!) because Jude had an affair with his children’s nanny. You might think that betrayal absolves Sienna from what happened next, but you’ll have a harder time finding an excuse for Jude’s buddy Daniel.
This was the unexpected development: Sienna became briefly romantically involved with Daniel Craig, which the British tabloid The News of the World reported in October 2005. Then, nearly a decade later, during the newspaper’s infamous phone-hacking trial, a reporter testified that he had intercepted a voicemail Sienna left on Daniel’s phone. In the message, Sienna said she couldn’t talk because she was at London’s Groucho Club with Jude before telling Daniel she loved him. Sienna herself acknowledged in court that she likely left the message, although she insisted that telling Daniel she loved him was simply how she spoke to close friends.
During the 2014 trial, Jude said that when he learned of the affair, he called Daniel and confronted him about it. When his barrister asked him to describe the conversation, Jude said, “We had known each other for many, many years, so the conversation took all sorts of turns.” According to News of the World reporting, Jude demanded to know how Craig could do this to a friend.
3. Simon Cowell is famous for being brutally honest on American Idol, but in his personal life, he wasn’t exactly Mr. Honesty. In 2004, Simon befriended New York real estate developer Andrew Silverman and his wife, Lauren, while vacationing in Barbados. The three became close, regularly taking luxurious vacations together, and the Silvermans even stayed at Simon’s guesthouse in Los Angeles. But somewhere along the way, Simon and Lauren locked eyes and cooed, “It’s a yes for me.” It’s unclear exactly when the affair exactly began, but some reports cite 2012 (and one even suggested it began as early as 2009).
Then, in Jan. 2012, Simon invited Andrew and Lauren on a yacht vacation in St. Barts, and photographers captured images of Lauren affectionately running her fingers through Simon’s hair. Remember, her husband was aboard the boat! Later that year, photos taken on another boat trip caught Simon and Lauren actually KISSING. According to TMZ, Andrew was shocked when those photographs surfaced the following year.
But the real bombshell came on July 31, 2013, when news broke that Lauren was pregnant with Simon’s baby. At the time, Lauren was still married to Andrew, with whom she already had a 7-year-old son. Andrew had filed for divorce just weeks earlier, citing adultery and actually NAMING SIMON in the divorce papers. Andrew told the New York Observer, “I am a regular person, not a tabloid thing. It was a fascinating experience, unexpected and shocking.” Simon eventually acknowledged that he’d handled the whole thing badly, saying, “It is not something I am proud of or wanted to happen in terms of hurting anyone. It just happened. You have to deal with it and man up to it… You have to accept the responsibility and the criticism.”
4. Long before Billy Joel hit it big, he was struggling to make it as a young musician on Long Island. He was also best friends with a drummer named Jon Small, and the two played together in a rock band called Attila. Billy was so close to Jon that he actually lived with him, his wife, Elizabeth Weber, and their young son. You can see where this is going…
Billy and Elizabeth started spending more and more time together, and before long, they were falling in love. Billy later said he was attracted to Elizabeth because she was smart, outspoken, and unlike other women he’d known.
Things came to a head one night after a sold-out Attila show at a club in Amityville, Long Island. Jon was backstage drying his hair when he looked out the window and saw Billy talking to Elizabeth. Then, to his astonishment, Billy GOT INTO HER CAR AND DROVE AWAY WITH HER!
Jon suspected something was going on, so he jumped into his car and followed them back to the house where all three lived. When he arrived, he found Billy sitting at the piano with Elizabeth and her younger sister. Jon lost it, shoving Elizabeth’s sister through a screen door and punching Billy in the face, leaving him with a bloody nose. The fallout was catastrophic. Attila broke up, Billy was forced out of Jon’s home, and Elizabeth temporarily disappeared from both men’s lives. Billy started drinking heavily, and things got so bad that he was sleeping in laundromats because he had nowhere else to go.
But even after surviving that ordeal, Billy was still in a terrible place. He attempted to take his life a second time, this time by drinking furniture polish. And here’s where the story takes an extraordinary turn: The person who found Billy and rushed him to the hospital was JON SMALL! Yes, the very friend whose marriage Billy had helped destroy. “Even though our friendship was blowing up, Jon saved my life,” Billy recalled.
Jon eventually forgave Billy, suggesting in the documentary that Billy had been so devastated because he genuinely loved Jon as a friend and couldn’t bear the pain he’d caused him.
Afterward, Billy checked himself into a psychiatric observation ward. He was there for several weeks and later said the experience helped him realize that he could channel his painful emotions into songwriting.
Billy and Elizabeth eventually reunited and married in 1973, although they divorced in 1982. And remarkably, Billy and Jon repaired their friendship, with Jon later involved in the production of many of Billy’s music videos, including “Tell Her About It.”
5. Prue Leith is a beloved judge on The Great British Bake Off, but for years she harbored a shocking secret — she was having a 13-year affair with the husband of her mother’s best friend! Hold on, you’re thinking. The wonderfully cheerful judge who wears colorful glasses and offers gentle encouragement to contestants? That Prue Leith? Yep. The one and only. In the early 1960s, Prue traveled from South Africa to spend the summer in England with actor Nan Munro, who was one of Prue’s mother’s closest friends and had treated Prue almost like a daughter. Also at the home? Nan’s husband Rayne Kruger. Rayne, who was 18 years older than Prue, became her mentor and eventually served as chairman of her business. But their relationship didn’t stay professional.
Prue later recalled that their attraction began when Rayne kissed her in the kitchen, and despite knowing he was married to her mother’s best friend — a woman she considered a second mother — she began an affair with him. And they somehow managed to keep it secret for THIRTEEN YEARS.
Eventually, however, Prue decided she wanted children and couldn’t continue waiting. She ended the affair and ran away with another man, traveling to Austria and Egypt. That breakup apparently made Rayne realize he couldn’t live without her. He left Nan and persuaded Prue to return. They married in 1974 and remained together until Rayne died in 2002.
6. In the early ’70s, former Beatle George Harrison (who was married to model Pattie Boyd) began an affair with his ex-bandmate Ringo Starr’s wife, Maureen. Pattie spilled all the English breakfast tea in her autobiography Wonderful Tonight: George Harrison, Eric Clapton, and Me. She recalled finding George and Maureen locked in a room together, and George giving the spectacularly unconvincing explanation that Maureen was tired and had gone in there to lie down. “She was the last person I would have expected to stab me in the back,” Boyd writes, “But she did.” The marriage was over.
Even wilder, Beatles insider Chris O’Dell says she was sitting at Ringo’s kitchen table when George told him, “I’m in love with your wife.” O’Dell says Ringo responded, “Better you than someone we don’t know,” but was nevertheless heartbroken by what happened. (Ringo got remarried in 1981 to Bond girl Barbara Bach, so he’s doing alright.)
Somehow, George and Ringo’s friendship survived, and they even reunited in the ’90s to work on the Beatles’ reunion tracks “Free as a Bird,” “Real Love,” and “Now and Then.” When George died in 2001, Ringo called him “a best friend of mine,” adding, “I loved him very much.”
7. If you’re feeling bad for Ringo, you should know that George’s close friend Eric Clapton did the same thing to him! Eric became obsessed with George’s wife, Pattie, whom George met while the Beatles were filming A Hard Day’s Night in 1964, and began visiting the couple’s home more and more. Soon he was urging Pattie to leave George and run away with him. In his longing, he wrote one of rock’s greatest love songs about her: “Layla.” Eric invited Pattie over to hear his new song, and when she realized it was about her, she was overwhelmed.
Things came to a head at a party when George discovered Eric and Pattie talking alone in the garden. According to Pattie, Eric announced to George, “I’m in love with your wife.” As you might imagine, George wasn’t thrilled. He angrily told Pattie she could leave with Eric if she wanted. She chose to go home with George, although that wasn’t the end of Eric’s pursuit. He continued writing letters and trying to persuade her to leave her marriage. Eventually, Pattie’s marriage to George fell apart, and she and Eric married in 1979. But, just as Ringo remained friends with George, George remained friends with Eric and attended their wedding reception!
