1. Mila Kunis and Macaulay Culkin
Kunis and Culkin began dating in 2002, when she was 18 and he 22, and were together for a whopping eight years. “We grew up together,” the actress told Women's Health. “You find a steady rock in your life and that’s all you need.”
In 2018 during an interview on Dax Shephard’s podcast, Kunis admitted her break-up from Culkin was "horrible" - and mostly her fault. “I was an a**hole in my 20s and I’ll be the first to admit it[...] “It’s f*cked up what I did and it’s f*cked up how I did it".
2. Ashton Kutcher January Jones
Kutcher and Jones began dating in the late ‘90s when she was best known as a model and he was at the start of his career, playing Michael Kelso on That '70s Show.
Though they dated for several years, Kutcher was evidently not the most supportive of boyfriends and didn't believe Jones could become an actress. “He was like, 'I don’t think you’re going to be good at this'", the Mad Men star told GQ. "So — f—k you![...] If anything, I should thank him. Because the minute you tell me I can’t do something, that’s when I’m most motivated.”
3. Chelsea Handler and 50 Cent
The surprising duo met when 50 Cent, aka Curtis Jackson, appeared on Handler's late-night talk show in 2009, and started a relationship that lasted several months.
Last August Handler posted a photo of herself with Jackson, and captioned it: "my favorite ex @50cent (and the only ex-boyfriend I am still asked about in every interview)".
4. Keira Knightley and Jamie Dornan
The two gorgeous actors dated for nearly two years after meeting in 2003 while shooting an ad for Asprey. By then, Knightley was already a famous actress, with movies like Bend it Like Beckham and Pirates of the Caribbean, and Dornan was 'just' a model.
"There is a big pressure when you go out with someone such as Keira," The Fifty Shades star told the Daily Mirror after their split. "The man is meant to be the alpha in the relationship on the money and power front, and clearly I was not. You feel like you have to be dominant in other areas and that causes problems."
5. Britney Spears and Colin Farrell
In 2003 Britney Spears was the princess of pop, and Colin Farrel was becoming a big name in Hollywood. That same year, they shocked fans when they attended the premiere of Farrel's movie The Recruit together, holding hands and kissing in public.
“She’s just a mate,” the handsome Irish man told Entertainment Tonight, “Seriously, we just met a week ago, [we’re] having a laugh;" while Spears told W Magazine “Yes, I kissed him. … He’s the cutest, hottest thing in the world — wooh! … But it was nothing serious.”
6. Topher Grace and Anne Hathaway
The Oscar winner and the That '70s Show alum dated for two years between 1999-2001, when they were both making their first steps in Hollywood, so this was a first public relationship for them both.
Though the couple broke up they remain friends, and even played a romantic couple in 2010's Valentine's Day.
7. Ryan Gosling and Sandra Bullock
The pair met on the set of the 2002 psychological thriller Murder By Numbers, which they co-starred in, and despite their 16-year age gap, started a two-year-long relationship.
"I had two of the greatest girlfriend of all time. I haven't met anybody who could top them," Gosling told The Times about Bullock and his other famous ex-girlfriend, Rachel McAdams.
8. Evan Rachel Wood and Marilyn Manson
The Westworld star began dating the controversial musician after she met him at a party at Hollywood’s Chateau Marmont in 2006, when she was just 18. At the time Manson was married to burlesque artist Dita Von Teese, who he divorced a year later.
Despite criticism over their 18-year age difference, Wood and Manson dated for 4 years and even got engaged in 2010 - only to break up a year later. "I was craving danger and excitement", the actress told Rolling Stone magazine, and said she does not regret anything.
9. Jennifer Aniston and Adam Duritz
The Counting Crows frontman, who was apparently quite the ladies man, had a brief relationship with Aniston in 1995 when she was just becoming a household name with Friends.
Interestingly, two years later Duritz went on to date Aniston's friend and colleague, Friends' Courtney Cox. "They were nice girls and I went out with them and that was that", he later told Men's Health magazine.
10. Emma Stone and Kieran Culkin
The Oscar winner and the Succession star became an item in 2009, after meeting on the set of Paper Man, and dated for about a year and a half.
As Stone was not yet a big star at the time, not much is known about their relationship. She went on to date her Amazing Spider-Man co-star, Andrew Garfield, a year after the breakup, while Culkin married Jazz Charton in 2013.
11. Madonna and Tupac Shakur
The pop star and the rapper were introduced by actress Rosie Perez at the 1993 Soul Train Awards, and began a romantic relationship that lasted a few months.
In a letter Shakur wrote to Madonna from prison in 1995, a year before his murder (and which was put for auction last year) he apologized to the singer for ending things between them. He explained that he was worried about publicly dating a white woman because he “would be letting down half of the people who made [him] what [he] thought [he] was.”
12. Natalie Portman and Jake Gyllenhaal
Gyllenhaal dated some successful and gorgeous leading ladies, with the Thor star being one of his first famous girlfriends.
The two actors dated for a few months in 2006. They remained close friends after the breakup and even co-starred in 2009's movie Brothers, with Portman calling Gyllenhaal "perfect" in an interview with OK magazine.
13. Tom Cruise and Cher
The actor and the pop icon first met in 1985 at Sean Penn and Madonna’s wedding, and then met again at the White House, of all places. "A bunch of people who were dyslexic were invited to the White House, and Tom and I are both dyslexic,” she told the Mail on Sunday. "We didn’t go out till way later, but there definitely was a connection there.”
Cruise was only 22 at the time, 16 years Cher's junior, but she has said that he was "in her top five" list of all-time lovers.
14. Avril Lavigne and Brody Jenner
The Canadian pop-punk star started dating the reality veteran (and Kim Kardashian's stepbrother) in 2009, shortly after her divorce from first husband, Sum 41 frontman Deryck Whibley.
The couple were together for more than two years, but reportedly ended things as Jenner wasn't ready to settle down.
15. Johnny Depp and Kate Moss
The actor and the British supermodel dated for four years between 1994 and 1997 and were one of the biggest 'It couples' of the '90s.
Moss herself told Vanity Fair she had a hard time after separating from Depp: "There’s nobody that’s ever really been able to take care of me. Johnny did for a bit. I believed what he said. Like if I said, ‘What do I do?,’ he’d tell me. And that’s what I missed when I left. I really lost that gauge of somebody I could trust. Nightmare. Years and years of crying. Oh, the tears!”
16. Christina Applegate and Brad Pitt
Pitt dated some of Hollywood's most gorgeous women, and in the late '80s he has briefly dated Applegate who was then the star of Married... with Children.
The two arrived at the 1989 MTV Movie Awards together, but Applegate famously ditched Pitt that night to meet with another man - later revealed to be Skid Row's frontman, Sebastian Bach.
17. Sheryl Crow and Owen Wilson
The musician and the actor met in 1999 on the set of the movie The Minus Man, in which Crow made her acting debut as one of Wilson's character's victims, and dated for two years.
Crow later admitted that her song "Safe and Sound" was inspired by her relationship with Wilson.
18. Uma Thurman and Gary Oldman
The Kill Bill actress told Vanity Fair that she first met the renowned English actor in the late '80s. Oldman then divorced his first wife, actress Lesley Manville, and he and Thurman wed in 1990 when she was just 20.
The pair divorced two years later, and Thurman later called their marriage a "mistake". “We met when I was 18,” she told Vanity Fair. “He was 12 years older. It was a crazy love affair that ended, as it needed to. He was my first love. I had no prior experience.”
19. Jennifer Aniston and Paul Rudd
This is Aniston's second appearance on our list, and no wonder, since she's dated some of Hollywood's most interesting bachelors. Paul Rudd does seem like a bit of a deviation from her usual type, but the two dated after co-starring in the movie The Object of My Affection (1998).
We don't know when or why they broke up, but they have collaborated in several projects together since, such as on Friends where Rudd was a guest stat.
20. Seth McFarlane Amanda Bynes
In 2008 the Family Guy creator and the former child star, then 34 and 22 respectively, were seen at a party together, where McFarlane cut short a conversation with a reporter saying his "date" was waiting.
The two met when Bynes voiced a character on McFarlane's show, but it's unclear whether their relationship lasted much longer than that night.
21. Lisa Kudrow and Conan O'Brien
The Friends alum and the late-night host met before either of them was famous, when they were attending the same improv class.
"He was really smart, really funny, and he thought I was funny," Kudrow told More magazine. Eventually, they "found we were better as friends" and have remained buddies to this day.
22. Ellen Barkin and Johnny Depp
The Fear and Loathing in Las Vegas co-stars became an item in the late '90s after having met on set, around the time of Barkin's divorce from her first husband, actor Gabriel Byrne.
Barkin later accused Depp of being violent to her during the relationship, and he in turn said that she was angry with him after he jilted her love.
23. Rachel McAdams and Michael Sheen
The two actors met in 2010 when they were both working on Woody Allen's critically acclaimed Midnight In Paris.
After being in a long-distance relationship for more than two years the pair broke up in 2013. "Michael and I never spend more than three weeks apart", McAdams told Stella magazine when the two were still together. "We rack up a lot of air miles - but you have to be quite adaptable in this business whether you are in a relationship or not."
24. Alanis Morissette and Ryan Reynolds
The Canadian cuties met at Drew Barrymore’s birthday party in 2002, and instantly became a couple. Morissette told People magazine Reynold was “like a soul brother to me... except that I want to jump his bones.”
In 2004 the two got engaged, but three years later ultimately called it quits. "I've been on a constant journey toward finally surrendering and hitting the rock bottom that I've been avoiding my whole life", the singer told LA Times of their break-up, "so this was a huge, critical juncture for me.”
25. Cameron Diaz and Justin Timberlake
The singer and the actress met at the 2003 Kids Choice Awards, when the Charlie’s Angels star presented JT with the interesting “Best Burp” prize.
The couple was together for four years, until breaking up in 2007, reportedly after Timberlake had started a flirtatious relationship with now-wife, actress Jessica Biel.
26. Courteney Cox and Michael Keaton
The Friends star started dating "Batman" Keaton in 1989 after she told a mutual friend how much she liked Keaton in the movie Clean and Sober.
The talented pair lived together for six years, until breaking up in 1995. "It’s the most important relationship I’ve ever had, and I think he’s the most wonderful person I’ve ever met,” Cox told People a few months after their split.
27. Cindy Crawford and Richard Gere
The supermodel and the Hollywood heartthrob met at a Hollywood party in the late '80s, when Crawford was just 22, and married in Vegas in 1991, four years into their relationship.
Four years later the couple decided to separate, mainly due to their 17-year age-gap and different mentalities. “I think part of the problem in our relationship was that we were a lot of other things but I don’t know if we were ever friends — like peers, because I was young, and he was Richard Gere," Crawford told Oprah.
28. Edward Norton and Courtney Love
The unlikely couple met while working on The People vs. Larry Flynt in 1995 and started a four-year-long relationship, which also included an engagement.
They separated in 1999. "I watched the VH1 special about me[...[ It was just like, ‘Why didn’t she marry Edward Norton and become a movie star?’[...] I wasn’t ready to, I didn’t want to, I didn’t know how to," she told Bust magazine.
29. Brooke Shields and Nicolas Cage
In 1987, Cage arrived at the premiere of his film Moonstruck with 'It girl' Brooke Shields. Fans were very excited, but the two have reportedly only ended up dating for about a month.
That same year, Shields started seeing actor (and "superman") Dean Cain while they were both attending Princeton, and they dated for two years.
30. Kim Kardashian and Nick Cannon
The reality star and the comedian dated for a few months in 2006 but, according to Cannon, broke up after she had denied the existence of her now-famous sex tape.
"If she might have been honest with me I might have tried to hold her down and be like 'that was before me' because she is a great girl," Cannon said on The Howard Stern Show. "But the fact that she lied and told me that there was no tape? ['This was my issue]".
31. Gwyneth Paltrow And Ben Affleck
Paltrow is another star who has dated some of Hollywood's most gorgeous men. She met Affleck in 1997, after her split from fiancé Brad Pitt, at a dinner party hosted by the now-notorious Harvey Weinstein. The two went on to star in two films together: Shakespeare In Love and Bounce, and were together for three years.
“I think there are certain boyfriends where you are trying to work stuff out, right?", the actress told Howard Stern of their relationship. "Like, you’re trying to heal certain stuff from your childhood and he was very much a lesson in that way."
32. Matt Damon And Winona Ryder
The two actors met in 1997 through Gwyneth Paltrow, who was good friends with Ryder and dated Damon's BFF, Ben Affleck, at the time.
They broke up in 2000 but remained friends. "Matt couldn't be a greater, nicer guy," the actress told Blackbook magazine. "I'm really lucky that I'm on good terms with him."
33. Alexis Bledel and Milo Ventimiglia
The Gilmore Girls stars first met on set of the show, where they played love interest, and in 2002 took their on-screen romance to real life and began a very private relationship.
Bledel has even admitted that the couple was contemplating marriage, and told People magazine: "I think everybody who has been dating for more than a couple of years probably talks about it at some point." But, unfortunately, just like Rory and Jess their romance did not survive, and they broke up in 2016.
34. Drew Barrymore And David Arquette
Though Arquette and Barrymore played siblings in Never Been Kissed (1999), a few years prior their relationship was a lot different.
"[Drew and I] used to date when we were very young kids. Well, not little kids!", he revealed on What Happens Live. "She's just a lovely, sweet person. We used to run around and just be silly."
35. Joaquin Phoenix And Liv Tyler
The Joker star's first highly-publicized relationship was with none other than the gorgeous Liv Tyler. The two dated for over three years between 1995-1998 and even collaborated on the coming-of-age movie Inventing the Abbotts during that time.
Interesting tidbit: when Tyler was dating Phoenix, a devout vegan, she also became a vegan. However, once the relationship ended, she went back to eating meat.
36. Jennifer Lawrence and Chris Martin
The Oscar winner started dating the Coldplay frontman in the summer of 2014, shortly after her split from X-Men co-star Nicholas Hoult and Martin's divorce from ex-wife Gwyneth Paltrow.
Lawrence and Martin broke up for the first time in October 2014, but were then seen together again at the beginning of 2015. However, by August 2015 they were broken up for good.
37. Whoopi Goldberg And Ted Danson
Danson met Goldberg while being a guest on The Arsenio Hall Show in 1988, and they became good friends. However, a few years later they became romantically involved while making the movie Made in America.
As Danson was married at the time, his affair with Goldberg caused a scandal, and his divorce from his then-wife Cassandra Coates is known as one of Hollywood's costliest divorces.
38. Justin Timberlake and Fergie
The two songbirds briefly dated in 1996 when Timberlake, who was just a teenager, had just joined NSYNC, and Fergie a 21-year-old aspiring musician.
"One of my good friends was dating J.C. Chasez, and so we'd all hang out with 'N Sync. Justin and I would go out together and have fun and make out," the Fergalicious singer told Cosmpolitan. "We went to Hawaii together, but we were never serious. He was Mr. Right Now."
39. Matthew Perry and Julia Roberts
In 1995 Roberts, who was already a successful actress, joined Friends as a guest star, and her on-screen relationship with Matthew Perry's Chandler Bing soon continued also in real life.
The two dated for several months, in what was Perry's first highly publicized relationship.
40. Miley Cyrus and Nick Jonas
The singers and fellow Disney stars first met in 2006 at a charity benefit, when they were just teenagers, and dated for a year and a half, being each other's first serious relationship.
The pair broke up in late 2007, with Cyrus describing the breakup as "[it] seemed like my life was over, but everyone was still living”. A year later she released the song 7 Things which lists 'reasons she hates an ex-boyfriend', and hasn't denied allegations the song was about Jonas.
41. Sarah Jessica Parker and Robert Downey Jr.
Parker and Downey met in 1984 on the set of the film Firstborn, when they were just 18, and instantly hit it off and moved in together.
They remained together for seven years, but unfortunately Downey Jr.'s drug addiction wreaked havoc on the relationship. “I was so selfish,” the Iron Man star told The Huffington Post. “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."
42. Jennifer Lopez and Diddy
The singer and the rapper appropriately met on the set of a music video, in 1999, and even though Diddy was in another relationship, they quickly became an item.
Lopez and Diddy dated for two years, making some unforgettable, stylish red carpet performances during that time, including Lopez's iconic green Versace dress. They ultimately broke up in 2001, with Lopez hinting to infidelity on Diddy's part.
43. Julia Roberts and Kiefer Sutherland
The two renowned actors met in 1990 when they were both up-and-coming stars, on the set of sci-fi film Flatliners.
A year later, the now-engaged couple was set to marry in a big event - but days before the wedding Roberts decided to call the whole thing off. “I feel like Kiefer, for whatever reasons, tried to make it seem like he was the victim of the situation,” she told Entertainment Weekly at the time. “I quite honestly believe that Kiefer knows that it’s the best thing for himself and for me that it didn’t happen."
44. Michelle Rodriguez and Cara Delevingne
The Fast and the Furious star and the English supermodel, both self-proclaimed bisexuals, dated for five months at the beginning of 2014.
They reportedly ultimately broke up because Rodriguez was unhappy with Delevingne's constant partying lifestyle, and her relationship with other female celebrities such as Suki Waterhouse.
45. Liev Schreiber and Kristin Davis
The Sex and the City alum and the Ray Donovan star dated between 2000-2003, but very very mum about their relationship so we don't have much information.
After their breakup, Schreiber started dating actress Naomi Watts, and Davis started seeing renowned screenwriter Aaron Sorkin.
46. Kaley Cuoco and Henry Cavill
The Big Bang Theory star and "Superman" dated briefly in 2013, and were followed by paparazzi on their every outing, a fact which perhaps contributed to the relationship dying down.
"I had no one following me until I met Superman," Cuoco told Cosmopolitan. "I've been in this business for 20 years, and my whole life I could go anywhere, do anything. There had not been one paparazzi photo of me until like several months ago. The recognition was crazy."
47. Dax Shepard and Kate Hudson
The actors first met in 2006 at a party at Tobey Maguire's house and immediately hit it off, but as they were both seeing other people nothing romantic happened between them. A year later, when they were both single, they reconnected and dated for several months.
Though both say they were very "compatible", according to Shepard his jealousy of Hudson's success put a strain on the relationship. “I felt very ‘less than’ around you quite often,” Shepard admitted on his podcast. “I think I was just in the point where I was not gonna get hired for movies anymore — I had a bunch that didn’t work — and I’m like, ‘I don’t f—ing know what’s next’ and you were at that time making the most you ever made and having the most opportunity.”
48. Eva Longoria and JC Chasez
The Desperate Housewives alum and the NSYNC singer dated for a few months at the beginning of 2004, after her divorce from first husband, Tyler Christopher. The couple was spotted on several red carpet events, displaying some PDA, and even attended the 2004 Emmy Awards together.
"I think every relationship is a path to where you are today," the actress told Hola magazine in 2016. "Every wrong turn led you to the spot where you are, so it wasn’t necessarily the wrong turn at the time. I wouldn’t change anything - never.”
49. Renée Zellweger and Jack White
The actress and the acclaimed musician met in 2003 while filming the movie Cold Mountain, where White, who contributed several songs to the film's soundtrack, also had a minor acting role.
The couple dated for a year and a half, and even attended the 2004 Oscars together, where Zellweger won Best Supporting Actress for the film.
50. Mandy Moore And Zach Braff
The Scrubs alum and the This is Us star dated for two years, between 2004-2006, during which Moore even guest-starred on Braff's show.
However, the relationship seemed to have ended on not such good terms, with Moore calling the split an icing on a “really bad cake. The burned cake", in an interview with Marie Claire.
51. Naomi Watts and Heath Ledger
The beautiful Australian duo met in 2002 while working on the western movie Ned Kelly and went on to date for two years.
"We had a beautiful relationship, only a couple of years, but he was a man who was completely full of joy, and there was a lot of laughing and affection. He was really a very special soul and made a great impact on my life," Watts told More magazine in 2011, after Ledger's unfortunate passing.
52. Jennifer Love Hewitt and John Cusack
The two actors went on a few dated in 2003, and during one of them were photographed lovingly gazing into each other's eyes.
The Ghost Whisperer alum went on to marry twice since their short courtship, while Cusack himself never got married, telling Elle magazine "Society doesn't tell me what to do."
53. Michael Jackson and Lisa Marie Presley
Jackson first met the daughter of the "king of pop" in 1975 when she attended his concert as a child. Less than two decades later they began a romantic relationship, and got married in 1994.
The unlikely couple was married for two years, with Presley defending claims about them faking the relationship by telling ABC: "How can you fake this 24 hours a day - sleeping with somebody, waking up with somebody? I'm not going to marry somebody for any reason other than the fact that I fall in love with them."