7 Shocking Star Breakups: Who Called It Quits?

Ben and Jen, Gwyneth and Brad, Johnny and Winona. Some Hollywood romances were so epic and high-profile, people are still talking about them decades later. However, other famous pairings managed to slip under the radar or happened so fast, we hardly remember they ever walked down a red carpet together. Here are 7 stars you probably forgot ever dated.

1. Brad Pitt and Christina Applegate

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Juliette Lewis, Gwyneth Paltrow, and Jennifer Aniston were some of Brad Pitt’s most high-profile romances. But his brief fling with Christina Applegate went under the radar. The two rendezvoused back in the late 1980s, during the peak of Applegate’s Married…With Children fame and prior to Pitt becoming a household name. According to the gorgeous blonde, Jason Priestly brought Pitt over to her house for a barbecue and she ended up taking the 26-year-old as her date to the 1989 MTV Video Music Awards. However, their relationship didn’t even make it to the after party. Halfway through the show, she ditched him for another guy.

2. Tom Cruise and Cher

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This May to December romance between Tom Cruise and Cher occurred at the start of Tom’s insanely huge acting career. Tom was 23 and Cher, 38, when the duo reportedly met at – get this – Madonna and Sean Penn’s wedding. They next saw each other at a White House even. "We didn’t go out till way later, but there definitely was a connection there,” she told Event. Eventually, the two hooked up and engaged in a whirlwind romance, which she confirmed in a segment called "Truth or Cher" on Watch What Happens Live with Andy Cohen. When asked how Tom ranked in her list of lovers she said: “He was in the top five. It’s not a long list, just a good list.” According to Cher, she wished that things had worked out. "It could have been a great big romance, because I was crazy for him."

3. Ashton Kutcher and January Jones

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Brittany Murphy, Demi Moore, and now-wife Mila Kunis are Ashton Kutcher’s most high-profile lovers. But did you know that he once dated Mad Men star, January Jones? Jones told GQ in 2009 that her first boyfriend was Ashton Kutcher in 1998 to 2001, but he didn’t believe in her acting skills. "[He] was not supportive of my acting," she said. "He was like, I don't think you're going to be good at this. So—fuck you! He only has nice things to say now—if anything, I should thank him, because the minute you tell me I can't do something, that's when I'm most motivated."

4. Jenna Dewan and Justin Timberlake

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Shortly after Justin Timberlake’s high-profile split from Britney Spears, he started dancing (literally) with Jenna Dewan, who was a backup dancer at the time. "We dated, not that long. We were like friends...that dated," Dewan confirmed on Watch What Happens Live With Andy Cohen. "I was not the rebound! I was very clear not to be [that]."

5. Cindy Crawford and Richard Gere

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Cindy Crawford was at the start of her catwalk crawl at the age of 22 when she met Pretty Woman actor Richard Gere –17 years her senior – at a backyard BBQ hosted by famed photographer Herb Ritts. They wed in three years later in 1991 and were married four years before announcing their divorce in 1995. "I think I was more willing at 22 to be, like, 'Okay, I'll follow,' but then you start going, 'Well, I don't want to just follow—I want to lead sometimes and I want to walk side by side sometimes,'" she said about the split.

6. Edward Norton and Salma Hayek

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At the time, Edward Norton and Salma Hayek seemed to make sense as a couple, but now it’s hard to believe they ever dated. From 1999 to 2003 the duo walked the rep carpet together. While the romance didn’t pan out, years later she expressed gratitude for his role in her career, namely for helping out with Frida. "Thanks to a phalanx of angels who came to my rescue, including Edward Norton, who beautifully rewrote the script several times and appallingly never got credit," she wrote in a 2017 opinion piece for the New York Times.

7. Sarah Jessica Parker and Robert Downey Jr.

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Sarah Jessica Parker and Robert Downey Jr. were both 18 when they met on the set of the 1984 drama Firstborn. According to People, they moved in together just eight weeks after they began dating and stayed together for nearly seven years. According to RDJ, his drinking and drug use was responsible for their split. "I liked to drink, and I had a drug problem, and that didn't jibe with Sarah Jessica, because it is the furthest thing from what she is. She tried to help me. She was so miffed when I didn't get my act together," he told Parade.

In the unpredictable world of showbiz, celebrities often face career setbacks that can be challenging to overcome. However, some stars manage to rise above adversity and make impressive comebacks. In this article, we'll explore the inspiring journeys of ten legendary celebrities who overcame various obstacles to reclaim their fame and success. From Robert Downey Jr.'s triumphant return to the spotlight after battling addiction to Britney Spears' resurgence following personal and professional struggles, each story highlights the resilience and determination of these remarkable individuals. Read on to learn about them all.

1. Robert Downey Jr.

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Robert Downey Jr. is public about his struggles with addiction, which got him fired from the show Ally McBeal in 2001. Downey Jr. completed rehab and has been sober since 2003. In 2008, his acting career surged. He appeared in Tropic Thunder, earning an Academy Award nomination. That year, he also appeared as the title character in the Marvel film, Iron Man. Since then, Downey Jr. has played the role in several Marvel films and projects, including the Avengers franchise.

2. Britney Spears

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Britney Spears’ career has had many highs and lows. After starring in The Mickey Mouse Club as a child, she launched her singing career. In 2006, she unfortunately divorced her husband Kevin Federline, and suffered mental health issues that were mocked in the press, which included a rough performance of “Gimme More” at the 2007 MTV Video Music Awards. Spears’ career re-surged in 2008, with her chart-topping album Circus. She then followed it up with albums Femme Fatale, Britney Jean, and Glory, and appeared as a judge on The X Factor. In 2021, the #FreeBritney movement took over social media, and she was able to be legally released from her conservatorship that her family placed her in.

3. Brendan Fraser

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After starring in projects like The Mummy in the 90’s, actor Brendan Fraser took a step away from the limelight after being sexually assaulted. Fraser first came forward with his story in 2018. He told CBS Mornings, "I spoke up because I saw so many of my friends and colleagues who, at that time, were bravely emerging to speak their truth to power. And I had something to say, too." Since then, Fraser has returned to acting, notably starring in The Whale, which won him Best Actor at the Academy Awards.

4. Winona Ryder

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In the ‘80s and ‘90s, Winona Ryder was one of Hollywood’s brightest stars. She appeared in films like Heathers and Beetlejuice. Unfortunately, in 2001, she was arrested for shoplifting, which put her stardom on hold. Ryder came back into prominence in 2016, starring on Netflix’s mega-hit ‘80s horror series, Stranger Things.

5. Vanessa Williams

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Before making waves as an actress and singer, Vanessa Williams, was the first black woman to win the Miss America pageant in 1983. Unfortunately, she was forced to give up her crown after nude photos of her were published in Penthouse, without her consent. Williams decided to start her acting and singing career after that. She appeared in the film Bye Bye Birdie, on ABC’s Ugly Betty, and had hit singles like “The Right Stuff.”

6. Kate Bush

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Kate Bush was one of the most popular singers in the ‘80s. She released songs like, “This Woman’s Work” and “Wuthering Heights.” In 2022, Bush’s career had a massive resurgence. Her song “Running Up That Hill,” went viral on social media, after appearing in the fourth season of Netflix’s Stranger Things. The song then appeared on the fifteenth season of RuPaul’s Drag Race in 2023.

7. Ke Huy Kwan

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Ke Huy Kwan first came into prominence in the ‘80s, starring in the films, Indiana Jones and The Temple of Doom and The Goonies. In the ‘90s, he starred in films like Encino Man, before taking a break from acting, after struggling to find roles. However, in 2018 he decided to give acting another shot. Kwan starred in 2022’s Everything Everywhere All At Once, which earned him an Academy Award and a Screen Actors Guild Award.

8. Selma Blair

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Selma Blair was best known for her roles in Cruel Intentions, Legally Blonde, and American Crime Story: The People vs. OJ Simpson, where she starred as Kris Jenner. In 2018, Blair announced that her acting hiatus was due to her struggles with multiple-sclerosis. However, she returned to TV in 2022, appearing as a contestant on Dancing With The Stars. Despite high praise from the judges and fans, she had to drop out due to medical issues.

9. Justin Bieber

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Having been discovered on YouTube as a teen, Justin Bieber quickly became one of the most popular singers of the late 2000s and early 2010s. However, after his public breakup with Selena Gomez, Bieber was hit with a series of controversies. He had many run-ins with the law, including a DUI and a vandalism arrest. In 2015, Bieber began his comeback by hosting a Comedy Central roast of himself. He then appeared on the Jack U song “Where R U Now,” which earned acclaim. Bieber’s next album, Purpose, produced several hit singles.

10. D’Angelo

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D’Angelo was considered one of the hottest R&B singers, even getting the nickname “R&B Jesus.” However, he took a 14 year hiatus before releasing his third album in 2014. D’Angelo told GQ that he struggled with his personal life during this time, experiencing deaths in his family, dealing with substance abuse, and struggling with the pressure of fame.