#25. Gary Oldman & Uma Thurman
Gary Oldman and Uma Thurman are well-known and talented actors in Hollywood. Both of them have won many awards for their performances in movies and plays. Oldman and Thurman met on the set film of State Of Grace in 1990 and sparks flew around them. Let's see what happened to the couple!
Soon after, the couple got married but their love didn’t last long. Only two years after their marriage, the couple decided to divorce. Thurman moved on and in 1998 she got married to the actor Ethan Hawke and Oldman married the model Donya Fiorentino. In the end, both of them divorced again.
#24. Emma Watson & Chord Overstreet
Emma Watson rose to fame when she became part of the Harry Potter franchise films in the role of Hermione Granger. Watson also has been in movies like My Week With Marilyn and Little Women. On the other hand, Chord Overstreet became famous when he played the role of Sam Evans on the TV series Glee. Everybody went crazy when the actors started to date in February 2018.
But everything in Hollywood moves fast and the couple only managed to be together for only six months when they announced their separation. According to some tabloids, they were having a great time in their low-profile romance but things didn’t work out between them.
#23. Nicole Kidman & Lenny Kravitz
The Australian actress Nicole Kidman is well-known for her performances in movies like Days Of Thunder, Eyes Wide Shut and Lion. Kidman is one of the most famous actresses from the ‘90s, especially because of her high-profile romance with the American actor Tom Cruise. The couple divorced in the early 2000s and since then, many romances were awarded to the actress.
From singer Robbie Williams to actor Jude Law, it’s said that Kidman dated many famous men. But from 2003 to 2004, the Australian actress dated and also got engaged to the singer Lenny Kravitz. Although it seemed two opposites worlds and persons, both of them managed to have a one-year relationship. In addition, it’s said that Kravitz composed his catchy song “Lady” for Kidman.
#22. Robert Downey Jr. & Sarah Jessica Parker
Back in the early ‘80s, actors Robert Downey Jr. and Sarah Jessica Parker were starting their acting careers in Hollywood. Parker rose to fame when she got the role of Carrie Bradshaw on the HBO TV series Sex And The City in the late-90s. Downey Jr. is most known for his performances in movies like Iron Man and Sherlock Holmes.
Downey Jr. declared many times that when he was a teenager, his life was complicated and hard as he was surrounded by drugs and when he started to date Parker in 1984, things went worst. The couple first met on the film set of Firstborn and had a relationship from 1984 to 1991 when the actress decided to break up with him because of his drug addiction. Later, Parker declared that it was really hard for her as she was the only person that held him together.
#21. Liam Neeson & Helen Mirren
Helen Mirren is considered one of the most talented actresses in Hollywood. Her most memorable performances are in the film The Queen in the role of Queen Elizabeth II and in the film The Audience with the same role. On the other hand, Liam Neeson is one of the most loved actors and his performances in Schindler’s List and Star Wars are still remembered.
The pair met on the film set of Excalibur in the early 1980s. Both of them lived a brief romance that meant a lot to them, they even lived together for a while. In some interviews, Neeson declared that Mirren helped him in his incipient acting career. Both of them are nowadays very close friends.
#20. Brad Pitt & Alia Shawkat
Brad Pitt is considered one of the most talented actors from the film industry, especially for his recent roles in the films Once Upon A Time In Hollywood and Ad Astra. Sadly for the actor in the last few years, his personal life has been under the public eye more than his professional career. After his high-profile divorce from the actress Angelina Jolie, all the tabloids want to discover who is dating Pitt.
Although it’s not official, Pitt has been seen going out many times with the actress Alia Shawkat, who is very famous for his role as Maeby Fünke in the TV series Arrested Development. According to some rumors, they’re just very good friends. Besides that, many fans are waiting for the back of Pitt and actress Jennifer Aniston!
#19. Mila Kunis & Macaulay Culkin
This is probably one famous past relationship that you might forget, we mean the one of Mila Kunis and Macaulay Culkin. Believe it or not, the couple was together for almost 10 years! They first met in 2002 and ended their relationship in January 2011. According to both of them, the breakup was in very friendly terms.
During their longtime romance, both of them managed to be away from the flashes and media attention. In words of Kunis: “I keep my personal life as I physically, mentally, possibly can”. Nowadays, the actress is married to actor Ashton Kutcher and together they had two beautiful children and Macaulay is in a relationship with actress Brenda Song.
#18. Meg Ryan & Russel Crowe
Meg Ryan is definitely the actress from the 90s romantic comedies as she was in films like Sleepless In Seattle, French Kiss and You’ve Got Mail. Ryan married the actor Dennis Quaid in 1991 and had a son together. According to some tabloids, things were not working out for the couple when Ryan met her co-star, the actor Russel Crowe, in the set film of Proof Of Life in 2000.
If the actors ever had a secret romance that was something that couldn’t be public. At that time, Crowe was in an on-again, off-again relationship with the singer Danielle Spencer. According to some tabloids, the secret romance didn’t last long and Crowe continued his relationship with Spencer but Ryan filled the divorce to Quaid in 2001.
#17. Alanis Morrisette & Ryan Reynolds
Did you know that Canadian singer Alanis Morrisette and the Canadian actor Ryan Reynolds once shared more than citizenship? As you’re reading, Morrisette and Reynolds were together for almost 4 years! The pair first met at Drew Barrymore’s birthday party in 2002 and soon after, both of them started to date.
In June 2004, the couple announced their engagement but their love didn’t last forever and in 2007, they announced their breakup. According to the singer, the release of her album Flavors Of Entanglement was the catharsis she needed after the end of the relationship. Also, in the past, the actress dedicated her famous single “You Oughta Know” to her ex-boyfriend Dave Coulier.
#16. Chelsea Handler & 50 Cent
Believe it or not, in 2011 rumors about an incipient romance between the businesswoman and comedian Chelsea Handler and the rapper 50 Cent were in all the magazines. According to some tabloids, the two of them started to date but they never confirmed the romance.
At that time, Handler loved to show herself in the company of the rapper having a good time together. Their love demonstrations were tender and bizarre. Still these days, we don’t if the relationship was real or not but we’re sure they are no longer together.
#15. Lamar Odom & Taraji P. Henson
The basketball professional player had been many times under media attention not for the best reasons. In 2009, Lamar Odom married to Khloé Kardashian after only month dating. Together they were part of the reality TV show Khloé & Lamar in the company of Lamar’s two children. The marriage ended up in 2013 after many months of speculation. Later, Odom had many personal troubles.
What many people don’t know is that before started dating Khloé, Odom was already seeing someone, the incredible actress Taraji P. Henson, who is well-known for her role in The Curious Case Of Benjamin Button. Nowadays, both of them never talk about their brief romance.
#14. Yvette Nicole Brown & Zachary Levi
The American actress Yvette Nicole Brown is well-remembered for her role as Shirley Bennet in the TV comedy Community. Brown has also been in TV series like That ‘70s Show, The Office, Boston Legal and The Soul Man. On the other hand, Zachary Levi is well-known for his singing career.
The pair met on the set of Chuck where Levi was in the role of Chuck Bartowski. What most people don’t know is that the pair had a short romance off-screen. They went together to many events in 2011 and they looked adorable!
#13. Bradley Cooper & Renee Zellweger
Both of them are Hollywood stars and very talented actors. Renee Zellweger is well-known for her role as Bridget Jones and Bradley Cooper has managed his personal issues and nowadays he’s a talented actor and director. If you were young in the 2000s, probably you won’t remember that the pair once were in love.
Zellweger and Cooper met in 2009 on the film set of Case 39 and after many months of rumors about their “good friendship”, they admitted they were dating. The romance didn’t last long and the couple split up in 2011 and according to some tabloids, the reason behind it was Cooper’s famous career.
#12. Scarlett Johansson & Ryan Reynolds
Soon after Ryan Reynolds broke up with Alannis Morisette in 2007, he started to date the beautiful actress Scarlet Johansson. Both of them looked incredible together and they were considered one of the hottest couples in all Hollywood. Reynolds and Johansson got engaged in May 2008 and got married in 2008.
Their marriage didn’t last for long and both of them decided to divorce in 2010. Soon after, the actress declared that her marriage with Reynolds was a “competitive union”. Nowadays, Reynolds is married to the actress Blake Lively and together they have three daughters.
#11. Will Smith & Tyra Banks
Nowadays, Will Smith has a strong and longtime marriage with actress Jada Pinkett Smith, together they have a beautiful family with their children Jaden and Willow and Smith’s son, Willard. But back in the time when The Fresh Prince Of Bel-Air was on air int he early 1990s, Smith had a brief but intense romance with his co-star, the supermodel Tyra Banks.
The pair dated from a year between 1993 and 1994 when they first met on the set film. Smith later met his current wife and married in 1997. On the other hand, Banks is in a relationship with the Norwegian photographer Erik Asla and together they welcomed their first son in 2016.
#10. Hank Azaria & Helen Hunt
Helen Hunt is one of the beloved actresses in Hollywood and she is well-remembered for her roles in the films As Good As It Gets and What Women Want and in the sitcom Mad About You. In the late-90s she met the actor Hank Azaria on the set of Mad About You.
Azaria is well-known for play several The Simpsons’ characters, like Moe, Apu and Chief Wiggum and also for his famous role as Mike in the TV series Friends. The couple got married in 1999 and divorced only 17 months later. It didn’t last for long but fans adored their romance.
#9. Nicolas Cage & Patricia Arquette
Nicolas Cage is one of the most famous actors in Hollywood, he has been in many films in his life, including films like Raising Arizona, Honeymoon In Vegas, Leaving Las Vegas and Con Air. When the American actor first met the actress Patricia Arquette, he immediately fell in love with her.
It’s said that Cage was so dazzled by Arquette’s beauty that he proposed to her the same night they met. Surprisingly, the marriage last from 1995 to 2001. Keep on reading the unknown and low-profile breakup in Hollywood!
#8. Brooke Shields & Andre Agassi
The American actress Brooke Shields is one of the most famous actresses from the ‘80s and ‘90s. Shields is well-remembered for her performance in the films Pretty Baby and The Blue Lagoon. Shields’ first marriage was with the famous tennis player Andre Agassi, from 1997 to 1999.
The couple had a short marriage that it supposed that ended in good terms but in 2014, Shields released her memoirs and talked about her first marriage. The actress declared that she was all the time with the tennis player, even in his dark moments related to drug abuse. Also, Shields declared that she was the only one who knows that Agassi wore hairpieces!
#7. Angelina Jolie & Jonny Lee Miller
Before the phenomenon of “Brangelina”, the American actress Angelina Jolie dated and married a few times. Since she was a teenager, she had intense and long romances. When Jolie was part of the 1995 film Hackers, she met the actor Jonny Lee Miller. They fell in love immediately and got married in 1996.
On the day of the wedding, Jolie decided to go in black rubber pants and a white T-shirt with MIller’s name on it. What is most bizarre is that Miller’s name was written in her blood! We don’t if that was the reason behind the divorce but the marriage only lasted for one year.
#6. Geena Davis & Jeff Goldblum
Geena Davis has been in many famous films from the ‘90s, like The Fly, Beetlejuice and Thelma& Louise. On the other hand, Jeff Goldblum was part of highest-grossing films from the ‘90s, Jurassic Park and Independence Day. Both of them were consolidated actors and fans went crazy when they announced their marriage in 1987.
The couple was together in two films, The Fly and Earth Girls Are Easy. Sadly, the couple couldn’t make more films together because they split up in 1990 without any reason. Soon after, both of them continued with their lives.
#5. Richard Gere & Cindy Crawford
Richard Gere is considered one of the most good-looking actors of all time. We all remembered him from films like Pretty Woman, Runaway Bride and Chicago. Nowadays, Gere is married to the Spanish activist Alejandra Silva and together they have one son. But back in the ‘90s, Gere dated and then married American supermodel Cindy Crawford.
The couple looked great and adorable together and both of them were are the top of their careers. The marriage lasted from 1991 to 1995 when they divorced. In a 2014 interview, the supermodel declared that she never felt a real company of her husband as she was “very young” and he was “Richard Gere”.
#4. Laura Dern & Ben Harper
Laura Dern is most remembered for her performances in David Lynch’s productions, like the film Blue Velvet and Twin Peaks: The Return. Also, Dern has been in recent movies like Marriage Story and Little Women. In the early 2000s, Dern met the rock & soul musician Ben Harper after going to one of his concerts.
The pair got married in December 2005 in their home at Los Angeles and had two children together. In 2010, Harper filed for divorce but soon after, the couple reconciled. Three years later, Dern decided to divorce from Harper. Don't miss the last 3!
#3. Zooey Deschanel & Ben Gibbard
New Girl star, actress Zooey Deschanel is considered one of the new promises of Hollywood. She is well-known because of her acting skills and his big and beautiful blue eyes. In 2008, she started dating Death Cab For Cutie frontman, Ben Gibbard.
Soon after they met, the couple got engaged in 2008 and married in September 2009. Their marriage didn’t last long and the couple announced their breakup in November 2011. Nowadays, both of them are with new partners and have only good things to say about their former marriage.
#2. Whoopi Goldberg & Ted Danson
The American actress Whoopi Goldberg is the type of actress that is loved by many generations. Goldbergs is considered one of the best comedian actresses of all time. Back in the ‘90s, the actress was romantically linked to the actor Ted Danson, who is well-known because of his recent role as Michael in the Netflix series The Good Place.
Danson described Goldberg as a “sexy and funny woman” but everything ended in a scandal when Danson appeared in blackface at a Friars Club doing a monologue about black people. According to Goldberg, she helped Danson to create the monologue and the intention was to used irony and black humor but in the end, it didn’t work. The couple announced their breakup soon after.
#1. Elisabeth Moss & Fred Armisen
The Handmaid’s Tale star, actress Elisabeth Moss is nowadays at the top of her career. Also, Moss has been in films like Us and The Invisible Man. Moss went to a program of the classic Saturday Night Live starring Fred Armisen and sparkles flew around them. The couple got married in October 2009.
But only eight months later, Moss filed the divorce from Armisen in June 2010. Soon after, the actress declared that her marriage was a traumatic experience and that Armisen was a terrible husband. Surprisingly, the SNL star admitted that he was a bad husband and that he got freaked out after the couple married.