#30. Sofia Vergara & Enrique Iglesias
Nowadays, we know Sofia Vergara as the star of Modern Family and the wife of Joe Mangianello. We also know Enrique Iglesias as one of the most prominent pop stars in the music industry who has been dating tennis player Anna Kournikova for almost 20 years.
Back in the '90s, Vergara and Iglesias were one of the most attractive couples in Hollywood. Neither of them were huge stars yet, so their breakup kind of went under the radar.
#29. Pink & Joey Fatone
In the late '90s and early 2000s, 'N Sync was one of the top music groups around, and each and every one of its members was under a lot of scrutiny. This forced Joey Fatone to keep his relationship with fellow pop singer Pink private.
They had a brief romance and did very cute stuff like going out for ice cream together. According to Pink, Fatone was very in love, but she didn't reciprocate the feelings.
#28. Natalie Portman & Jake Gyllenhaal
Natalie Portman and Jake Gyllenhaal were a Hollywood dream together. The two had a short relationship in 2006 and formed a strong bond with each other, and even though it didn't work out, the two remained good friends.
Whenever the topic comes up they only have great things to say about each other. And if it had worked out, imagine what their babies would've looked like!
#27. Helen Hunt & Matthew Broderick
It is very hard to imagine Matthew Broderick without long-time love Sarah Jessica Parker, but there was a time when all his attention was devoted to Helen Hunt -1987 to be exact.
The two enjoyed a brief relationship that was a teenage love more than anything else. The two reunited when they starred in Then, She Found Me together in 2008 and remembered their time together fondly.
#26. Minka Kelly & Donald Faison
Although the two of them are kind of out of the spotlight nowadays, Minka Kelly and Donald Faison were a big couple in the 2000s. Kelly was the star of Friday Night Lights and Faison starred in Scrubs, two very popular shows at the tme.
The two were together in 2005 but it didn't last very long. Still, they attended their fair share of red carpets together.
#25. Salma Hayek & Edward Norton
Salma Hayek and Edward Norton didn't meet at a movie set or at a fancy event like the Oscars. In fact, they were set up on a date by their chiropractor! The man seemed to know what he was doing, because they really hit it off and were together for four years.
After their breakup, they stayed in good terms and even worked together on the script for Frida, the Frida Kahlo biopic that made Hayek a superstar.
#24. Ryan Reynolds & Alanis Morisette
Ryan Reynolds and Alanis Morisette were one of those couples that seemed like they would last forever. They met at Drew Barrymore's birthday party in 2002 and totally hit it off, and went on to date for 5 years.
They were set to get married but Reynolds allegedly broke it off before it could happen. Morisette famously wrote a whole album about their breakup, which didn't make Reynolds look good at all.
#23. Drew Barrymore & Luke Wilson
Drew Barrymore and Luke Wilson enjoyed a very low-key romance in 1997 after they co-starred in Home Fries together. Interestingly, they had been friends for a long time before, but sparks flew when they were on set together.
After the breakup, the two kept their friendship alive, something that was very important to Barrymore, according to Wilson himself.
#22. Tiffani Thiessen & Ryan Seacrest
Tiffani Thiessen was a big star back in the day thanks to her work on Saved by the Bell and Beverly Hills 90210.
At the same time, Ryan Seacrest was a rising star and the host of American Idol, so it only made sense for these two up-and-comers two hook up. It only lasted for a month, however.
#21. Scarlett Johansson & Josh Hartnett
Scarlett Johansson and Josh Hartnett got together in 2006 after co-starring in Black Dahlia. Although the movie wasn't a big hit, their relationship was very popular among fans.
They seemed to have potential as Hollywood's next power couple, but their crazy schedules tore them apart.
#20. David Spade & Julie Bowen
David Spade and Julie Bowen seem like an odd couple, but the two really hit it off when they met in 2002. Back then, Bowen was still trying to make a name for herself in the industry, while Spade was already a star.
The two were together for one year before they called it quits. Nowadays, Bowen is the bigger star, oh how times change!
#19. Penelope Cruz & Tom Cruise
Tom Cruise had a ton of high-profile relationships and was married a whopping three times. In between marriages, he dated Penelope Cruz, and the two seemed to be together for the long run.
They were together for three years and called it quits allegedly because their busy schedules kept them apart. He then went on to marry Katie Holmes in one of the most extravagant weddings in celebrity history just a year later.
#18. Hilary Duff & Joel Madden
Hilary Duff was the perfect Disney girl in the early 2000s, but when Lizzie McGuire was over, she began dating Good Charlotte frontman Joel Madden, who had a sort of bad boy image.
The two seemed like they came from two different worlds, but somehow, they were great together. Their young love only lasted two years though, and Madden moved on to his current wife, Nichole Richie.
#17. Cameron Diaz & Matt Dillon
Cameron Diaz and Matt Dillon were one of the cutest couples in the '90s. The two were showing up to red carpets together and couldn't keep their hands off each other, and even worked on a movie together, There's Something About Mary.
After three years the two went their separate ways, and Dillon went on to say that Diaz was his "muse".
#16. Drew Barrymore & Edward Norton
In true Hollywood fashion, Drew Barrymore and Edward Norton got together after meeting on the set of a movie. Just like their characters in Everyone Says I Love You, the young actors fell madly in love with each other.
Although they ended up together in the movie, life did not imitate art this time, and the two separated after just a few months. Back then, Norton was caught up in a scandal because he began dating Barrymore's close friend, Courtney Love, just a few weeks after their breakup.
#15. Sandra Bullock & Ryan Gosling
Sandra Bullock and Ryan Gosling met on the set of Murder by Numbers in 2002, but because of their 16-year age difference, they got a lot of press, some good and some bad.
The two however really hit it off and did many red carpets together. They called it quit after one year, but the relationship made a big impact on them, especially in Gosling, who called Bullock one of the "greatest girlfriends of all time".
#14. Natalie Portman & Gael Garcia Bernal
Natalie Portman had her fair share of celebrity relationships before she found her husband, Benjamin Millepied. All the way back in 2003, Portman dated Mexican actor Gael Garcia Bernal, and the two dated for one year in 2004.
Although it seemed that they were over, they got back together in 2006. They couldn't make it work, however, and in 2007, they broke up for good.
#13. Johnny Depp & Kate Moss
Remember when Johnny Depp and Kate Moss were a thing? The two were caught in an intense relationship that had very high highs and very low lows.
One moment, they were all over each other, and the next, they were destroying hotel rooms and doing all kinds of strange stuff together. Their trainwreck of a relationship ended in 1998 after four years.
#12. Chris Evans & Jessica Biel
Back when both were struggling actors trying to make a name for themselves, Chris Evans and Jessica Biel dated. The two met when they filmed Cellular. The movie got terrible reviews, but they got a relationship out of it at least!
They were together for five years and remained friends after their separation. Biel later met Justin Timberlake, her current husband. Evans on the other hand, is still looking for the one.
#11. Amy Poehler & John Stamos
Amy Poehler was married to Will Arnet for many years and the two had a painful divorce. When she got back in the dating game, she went out with John Stamos, but their fling was nothing but awkward.
According to Stamos, he was really into her, but she only saw him as a friend. The worst part is that he heard this from a friend rather than from Poehler. If John Stamos is getting friendzoned, what is left for the rest of us?
#10. Nicole Kidman & Tom Cruise
Nicole Kidman and Tom Cruise had a very intense relationship for a whole decade. They got married shortly after they began dating and later adopted two children. The two starred in several movies together and were the hottest Hollywood couple for many years.
Then, they went through a harrowing divorce, which left Cruise with custody of their children. Because Kidman left the Church of Scientology after that, her children refused to speak to her ever again. She recently revealed that she is trying to reconnect with them but with no success.
#9. Jared Leto & Scarlett Johansson
The fact that Jared Leto and Scarlett Johansson dated seems to have escaped society's collective mind altogether, but it was a very real thing. The two had a very low profile relationship in 2004, before Johansson left him for her now ex-husband Ryan Reynolds.
The two did stay on good terms and there were even rumors that the two had a few encounters here and there over the years.
#8. Denise Richards & Charlie Sheen
Denise Richards and Charlie Sheen were an adorable couple in the early 2000s. They got married after eight months of dating and had two girls together, but then, Sheen's addiction problems began.
His erratic behavior became too much to handle and Richards had no choice but to file for divorce. She got custody of the girls and Sheen...well, we all know what he got himself into in later years.
#7. Courteney Cox & David Arquette
Courteney Cox and David Arquette got together at the height of her Friends fame. This made them a very high profile couple and they were all over the news.
They had a huge wedding and Cox famously added "Arquette" to her name, which can be seen on the credits of a few seasons of the show. Unfortunately, it only lasted for a few years, and they went through a very public divorce.
#6. Justin Timberlake & Cameron Diaz
The fact that Cameron Diaz and Justin Timberlake dated was a huge deal in 2003, but everyone kind of forgot about it. The two were together for three years and tried their best to keep their relationship private, but because they were both such huge stars, it was impossible.
The pressure of fame and the fact that Diaz wasn't ready to get married eventually broke them apart.
#5. Madonna & Sean Penn
How is it possible that we all forgot that Madonna and Sean Penn were married once? And for four years at that! The two were all over the place in the '80s and their divorce made headlines.
They still tried to remain friends after it was all over, and Madonna even testified in his favor when he was accused of domestic abuse.
#4. Jennifer Aniston & Tate Donovan
If you are an avid Friends rewatcher, you may recognize this couple from the show. But did you know that Jennifer Aniston and Tate Donovan actually dated in real life? Not only that, but their relationship was very serious.
They dated for three years from 1995 to 1998, which means that they had just broken up when Donovan guest starred in the show. it was after this breakup that she began dating Brad Pitt, and we all know how that went!
#3. Robert Downey Jr. & Sarah Jessica Parker
Robert Downey Jr. and Sarah Jessica Parker were meant to be. The two were rising stars in the film industry and had annoyingly long names. They were in a committed relationship for seven years, but Downey's addiction problems got in the way of their relationship.
The two reunited several years after to get some closure and have nothing but lovely words to say about each other.
#2. Joaquin Phoenix & Liv Tyler
Joaquin Phoenix and Liv Tyler were the perfect teenage couple in the '90s. People were so obsessed with them that they even did whole photoshoots for magazines.
They were each other's first love and enjoyed a very intense relationship for three years before going their separate ways. They are still friends and can be seen hanging out together from time to time and only have sweet things to say about each other.
#1. Winona Ryder & Johnny Depp
Winona Ryder and Johnny Depp were one of the most intense couples Hollywood has ever seen. On the one hand, they seemed to be deeply in love, but on the other hand, they were terrible for each other.
They began dating when Ryder was 16 and Depp was 24, and the age gap played a huge part in their breakup. He got her named tattooed on his arm and they were engaged for three years before calling it quits in 1994 with a scandalous breakup.