Remembering the Oddest Odd Couples of the '90s
(Photos: Getty Images)
Looking back, the '90s was a strange and wondrous time of juxtaposition. What other decade started out with grunge, wallet chains, and mumblecore and ended with boy bands, puka shells, and the Star Wars reboot? So maybe it makes sense some of the most OMG, WTF romantic pairings in pop culture also happened in the '90s.
Now that we're more than a full decade removed and most of these stars have moved on — some for better, some for worse — it's time we pay tribute to their random love connections.
Brad Pitt & Christina Applegate
Just two kids addicted to hairspray and ear piercings.
Robert De Niro & Naomi Campbell
This one's totally weird on the surface, but it makes sense that the guy who won an Oscar forRaging Bull could handle someone as volatile as Naomi Campbell.
Madonna & Vanilla Ice
The Material Girl needed some Ice, Ice baby before his 15 minutes of fame melted away.
Madonna & Dennis Rodman
The pair must have bonded over each having one of the most memorable wedding dress moments in pop culture history.
Danielle Fishel & Lance Bass
Nostalgia overload! Boy band meets Boy Meets World. Of course, we later learned Lance Bass was more a boy meets boy kind of guy.
Robert Downey Jr. & Sarah Jessica Parker
SJP put the "stand by your man" theory to the test, sticking with RDJ for seven years while he battled with drug and alcohol addiction. It must have been tough go, since Parker went the other direction marrying squeaky clean Mathew Broderick.
Edward Norton & Courtney Love
Something sparked on the set of The People vs. Larry Flynt, and brought these two together (even though Courtney Love seems way more like a Woody Harrelson kind of gal than theEd Norton type).
Michael Bolton & Ashley Judd
The guy everyone's mom had a crush on dating the only Judd guys ever had a crush on.
Kathy Griffin & Jack Black
Just two stand-up comics trying to make it in Hollywood. At least one of them got off the D-list.
Luke Wilson & Drew Barrymore
Luke Wilson aimed for leading man status but instead settled for dating his co-star after Best Men and Home Fries.
Julia Roberts & Matthew Perry
Matthew Perry was Julia Roberts' awkward bridge between Lyle Lovett and Benjamin Bratt, which seems about right. Right?
Sheryl Crow & Owen Wilson
Fun fact: Crow wrote the song "Safe and Sound" for Wilson, which, considering the lyrics, was eerily foreboding seeing as how he'd attempt suicide five years later. But everyone's okay now! Both are happy parents — PHEW!
Fiona Apple & David Blaine
Back when David Blaine did actual magic, he managed to trick Fiona Apple into being his girlfriend.
Sandra Bullock & Matthew McConaughey
All right, all right, all right — looks like there was a time to date after filming A Time to Kill.
Sean Penn & Jewel
During one of his many breaks from then-wife Robin Wright Penn, Sean got together withJewel and even directed the music video for "You Were Meant for Me," which turned out wasn't a good omen.
Neil Patrick Harris & Christine Taylor
In the days Doogie Howser and Hey Dude, the future Mrs. Ben Stiller probably had no idea NPH would eventually play for the other team.
Danny Wood & Halle Berry
This New Kid had the right stuff (at least until Halle Berry grew out of her boy band phase).
Johnny Depp & Ellen Barkin
Demi Moore must have learned her best moves from Ellen Barkin.
Courteney Cox & Michael Keaton
For a time, Courteney Cox was Batman's best Friend.
Ryan Reynolds & Kristen Johnston
Ryan Reynolds relationship trajectory: The 3rd Rock from the Sun star to Alanis Morissette to Scarlett Johansson to Blake Lively. Make of that what you will.
Ashton Kutcher & January Jones
Nope, this wasn't an elaborate Punk-ing. Before Kutcher had Kunis and Jones had Mad Men, they had each other.
Julie Bowen & David Spade
The eventual Modern Family mom may have starred opposite Adam Sandler in Happy Gilmore, but David Spade was the SNL alum who won her over.
Seal & Tyra Banks
Two Sports Illustrated swimsuit covergirls?! Seal is really good at life.
Just two kids addicted to hairspray and ear piercings.
Robert De Niro & Naomi Campbell
This one's totally weird on the surface, but it makes sense that the guy who won an Oscar forRaging Bull could handle someone as volatile as Naomi Campbell.
Madonna & Vanilla Ice
The Material Girl needed some Ice, Ice baby before his 15 minutes of fame melted away.
Madonna & Dennis Rodman
The pair must have bonded over each having one of the most memorable wedding dress moments in pop culture history.
Danielle Fishel & Lance Bass
Nostalgia overload! Boy band meets Boy Meets World. Of course, we later learned Lance Bass was more a boy meets boy kind of guy.
Robert Downey Jr. & Sarah Jessica Parker
SJP put the "stand by your man" theory to the test, sticking with RDJ for seven years while he battled with drug and alcohol addiction. It must have been tough go, since Parker went the other direction marrying squeaky clean Mathew Broderick.
Edward Norton & Courtney Love
Something sparked on the set of The People vs. Larry Flynt, and brought these two together (even though Courtney Love seems way more like a Woody Harrelson kind of gal than theEd Norton type).
Michael Bolton & Ashley Judd
The guy everyone's mom had a crush on dating the only Judd guys ever had a crush on.
Kathy Griffin & Jack Black
Just two stand-up comics trying to make it in Hollywood. At least one of them got off the D-list.
Luke Wilson & Drew Barrymore
Luke Wilson aimed for leading man status but instead settled for dating his co-star after Best Men and Home Fries.
Julia Roberts & Matthew Perry
Matthew Perry was Julia Roberts' awkward bridge between Lyle Lovett and Benjamin Bratt, which seems about right. Right?
Sheryl Crow & Owen Wilson
Fun fact: Crow wrote the song "Safe and Sound" for Wilson, which, considering the lyrics, was eerily foreboding seeing as how he'd attempt suicide five years later. But everyone's okay now! Both are happy parents — PHEW!
Fiona Apple & David Blaine
Back when David Blaine did actual magic, he managed to trick Fiona Apple into being his girlfriend.
Sandra Bullock & Matthew McConaughey
All right, all right, all right — looks like there was a time to date after filming A Time to Kill.
Sean Penn & Jewel
During one of his many breaks from then-wife Robin Wright Penn, Sean got together withJewel and even directed the music video for "You Were Meant for Me," which turned out wasn't a good omen.
Neil Patrick Harris & Christine Taylor
In the days Doogie Howser and Hey Dude, the future Mrs. Ben Stiller probably had no idea NPH would eventually play for the other team.
Danny Wood & Halle Berry
This New Kid had the right stuff (at least until Halle Berry grew out of her boy band phase).
Johnny Depp & Ellen Barkin
Demi Moore must have learned her best moves from Ellen Barkin.
Courteney Cox & Michael Keaton
For a time, Courteney Cox was Batman's best Friend.
Ryan Reynolds & Kristen Johnston
Ryan Reynolds relationship trajectory: The 3rd Rock from the Sun star to Alanis Morissette to Scarlett Johansson to Blake Lively. Make of that what you will.
Ashton Kutcher & January Jones
Nope, this wasn't an elaborate Punk-ing. Before Kutcher had Kunis and Jones had Mad Men, they had each other.
Julie Bowen & David Spade
The eventual Modern Family mom may have starred opposite Adam Sandler in Happy Gilmore, but David Spade was the SNL alum who won her over.
Seal & Tyra Banks
Two Sports Illustrated swimsuit covergirls?! Seal is really good at life.
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