Iconic celeb couples of past MTV Video Music Awards ceremonies09/08/2021
In honor of the 2021 MTV Video Music Awards on Sept. 12, Wonderwall.com is taking a look back at some of the most iconic celeb couples of past VMAs — from Bey and Jay to Kurt and Courtney and everyone in between! Keep reading to take a look back at the power couples we seriously shipped back in the day, starting with these pop stars… Justin Timberlake and then-girlfriend Britney Spears looked cozy while cuddled up together in the audience during the 2000 MTV VMAs. The *NSYNC singer and the Princess of Pop, who were childhood friends and colleagues, took their relationship to the next level in 1999. They called it quits in 2002 amid rumors she was unfaithful.
Now keep reading for more of the most unforgettable couples of MTV VMAs past…
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Long before triple-threat Jennifer Lopez made a name for herself as one of the biggest stars in Hollywood, she was known predominantly for her relationship with Diddy. The two music stars coordinated in white ensembles during the 2000 MTV VMAs. They were an item from 1999 to 2001.
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Less than a year before his tragic death in April 1994, Kurt Cobain joined wife Courtney Love and their toddler daughter, Frances Bean Cobain, at the 1993 MTV VMAs. The Nirvana rocker and the Hole frontwoman tied the knot in 1992 and welcomed their little girl later that year.
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Then-newlyweds Michael Jackson and Lisa Marie Presley made waves with the way they opened the 1994 MTV VMAs: The duo took the stage hand-in-hand to thunderous applause from the live studio audience. “Just think, nobody thought this would last,” said the King of Pop. He and his wife of four months then shared a big, awkward kiss. But it turns out the critics were right: A year and a half later, she filed for divorce.
JAY-Z joined then-girlfriend Beyonce on stage during the 2003 MTV VMAs for a rendition of their hit single “Crazy in Love.” They didn’t publicly reveal they were a couple until the following year — although, if we’re being totally honest, we all knew they were secretly an item!
It’s one of the most iconic moments in red carpet history: Marilyn Manson sported a colorful animal-print suit while posing with then-girlfriend Rose McGowan — who donned a completely see-through, open-back beaded LBD that barely qualified as a dress — during the 1998 MTV VMAs. They got engaged not long after that but split in 2001.
Aw, young love! Taylor Swift and Joe Jonas sat together in the audience during the 2008 MTV VMAs, which landed smack in the middle of their highly publicized three-month courtship. Mere weeks after this photo was taken, the Jonas Brothers singer infamously dumped the country-pop cutie in a 27-second phone call.
What could’ve been! Brad Pitt and Christina Applegate became pals and briefly dated in the late ’80s — he even joined her at the 1989 MTV VMAs as her date. But the “Married… With Children” star infamously ditched the handsome young actor to hang out with another man during the award show. During a 2015 appearance on “Watch What Happens Live,” Christina confirmed that she did, in fact, bail on Brad at the VMAs, though she declined to name the man for whom she left him, saying simply that he’s well known but isn’t an actor.
The same month “Newlyweds” debuted, a super-glam Jessica Simpson joined husband Nick Lachey on the red carpet at the 2003 MTV VMAs. They’d been married for less than a year when the MTV reality show hit the small screen, catapulting the pop stars to an extreme level of fame that ultimately took a toll on their relationship. They separated in late 2005 — the same year “Newlyweds” came to an end.
All eyes were on Tommy Lee and third wife Pamela Anderson thanks to their wild ensembles — a trench coat, sneakers and a bucket hat for him and a corset top with intricately beaded pants and an oversized furry hat for her — during the 1999 MTV VMAs. The Mötley Crüe rocker and the “Baywatch” beauty were married from 1995 to 1998.
A few months before fans started to suspect that Justin Bieber and Selena Gomez were secretly dating, the young stars posed together at the 2010 MTV VMAs. They went on to date off and on for more than seven years. Their turbulent romance finally came to an end for good in early 2018 … mere months before he proposed to now-wife Hailey Bieber.
Carson Daly — who hosted MTV’s “Total Request Live” from 1998 to 2002 — dated teen idol Jennifer Love Hewitt for about a year in 1997 and 1998. They packed on the PDA while positing together during the 1998 MTV VMAs before calling it quits later that year.
Then-newlyweds Katy Perry and Russell Brand — who tied the knot in India in 2010 — shared the look of love while posing together on the red carpet at the 2011 MTV VMAs. Just four months later, however, the controversial English comedian filed for divorce.
Whitney Houston was literally all over then-husband Bobby Brown during the 1998 MTV VMAs. (Even the award show’s Moonman mascot looked a little jealous!) The music stars, who were married from 1992 to 2007, matched in gray suits that they both wore with black shirts and shoes.
It was the hiney-grab seen ’round the world: A booze-toting Kanye West gave then-girlfriend Amber Rose a squeeze on the red carpet at the 2009 MTV VMAs. The rapper and the model dated from 2008 to 2010.
Tommy Lee and Heather Locklear practically ruled the late ’80s! The Mötley Crüe rocker and the “Melrose Place” actress — who married in 1986 and divorced in 1993 — held hands at the 1989 MTV VMAs during the height of their run as a Hollywood power couple.
Pete Davidson and Ariana Grande brought their whirlwind romance to the 2018 MTV VMAs. At the time, they were just a few months into their relationship and subsequent engagement. But just two months after they were snapped packing on the PDA at the MTV award show, they’d gone their separate ways.
Make way for rock ‘n’ roll royalty! The late, great David Bowie attended the 1999 MTV VMAs with some very special arm candy: his supermodel wife, Iman. They wed in 1992 and were still going strong when he died from cancer in 2016.
Pop-punk power couple Ashlee Simpson and Pete Wentz presented an award together during the 2008 MTV VMAs while the singer-actress was pregnant with their son, Bronx Mowgli, who arrived less than three months later. (The pair tied the knot earlier that year in May 2008 and split in 2011.)
Rising stars and then-couple Sarah Jessica Parker and Robert Downey Jr. — who first connected when they co-starred in 1984’s “Firstborn” — attended the 1990 MTV VMAs together. They were an item from 1984 to 1991.
Before she was one-half of the power couple known as Robsten, Kristen Stewart dated “This Is Us” actor Michael Angarano. She brought him as her date to the 2008 MTV VMAs, which went down just two months before the first “Twilight” movie debuted, launching her to international superstardom. She and Michael dated from 2005 to 2009.
These two have been going strong for more than two decades! The same month Pink and Carey Hart celebrated their first anniversary of dating, they made one of their earliest public appearances as a couple at the 2002 MTV VMAs. They got engaged in 2005 and tied the knot in 2006.
We totally forgot they dated! Richie Sambora and Cher posed together backstage during the 1989 MTV VMAs. The Oscar-winning actress romanced many famous men over the years — from Tom Cruise and Val Kilmer to Gene Simmons, Gregg Allman and, yes, the Bon Jovi guitarist, from whom she reportedly split in 1990.
Kid Rock seemed very proud to have a scantily clad Pamela Anderson — his future ex-wife — on his arm at the 2001 MTV VMAs. They duo married in mid-2006 but split just a few months later.
Vivica A. Fox raised temperatures while posing with then-boyfriend 50 Cent at the 2003 MTV VMAs. Though they dated for only a brief period of time in the early 2000s, their relationship was incredibly serious. In 2018, the actress revealed that they nearly got engaged.
Yup, Joel Madden and Hilary Duff dated for quite some time before he met and married Nicole Richie and she wed now-ex Mike Comrie. The singer-actress was all smiles while posing with the Good Charlotte rocker at the 2005 MTV VMAs. They called it quits in late 2006 following two and a half years of coupledom.
Meanwhile, Benji Madden dated Paris Hilton for about nine months in 2008. They attended the 2008 MTV VMAs together but split just two months later.
Carmen Electra and Dave Navarro both managed to show some skin during the 2003 MTV VMAs: She donned a minidress with an unnecessary slit in the front, while he flashed his stomach in a tight-fitting tank. They married just three months later but separated in mid-2006.
Early in their relationship of more than two decades, Jada Pinkett Smith and Will Smith made it a date night at the 1997 MTV VMAs. Less than four months later, they became husband and wife.
Teen stars Ashlee Simpson and Ryan Cabrera briefly dated in 2004 — just long enough to attend the 2004 MTV VMAs together!
Yep, they dated! Fiona Apple brought then-boyfriend David Blaine as her plus-one to the 1997 MTV VMAs. The famed magician was on hand when the singer-songwriter picked up the award for best new artist and shared her gratitude by lecturing “everybody out there that’s watching” about how “this world is bulls***.” They split later that year.
Before his whirlwind romance with Ariana Grande, Pete Davidson dated writer Cazzie David — the daughter of comedy star Larry David — for about two years. The twosome even attended the 2017 MTV VMAs together! They split in May 2018 … the same month Pete and Ariana went public with their whirlwind romance.
Ice-T and wife Coco Austin, who tied the knot in 2002, donned matching cobalt blue ensembles during the 2006 MTV VMAs.
If Paula Patton had known about the controversy that would ensue following Robin Thicke’s scandalous performance with Miley Cyrus during the 2013 MTV VMAs, she might not have looked so happy while posing with her then-hubby before the show. She filed for divorce the following year after nearly a decade of marriage and more than two decades of coupledom.
Riff Raff and Katy Perry sparked romance rumors when they showed up to the 2014 MTV VMAs in coordinating denim ensembles — a tribute to the iconic denim-on-denim looks that Britney Spears and Justin Timberlake wore to the 2001 American Music Awards. It’s unclear if the rapper and the “Teenage Dream” chart-topper, who collaborated on the remix of her song “This Is How We Do,” ever actually dated, though they certainly leaned into the buzz surrounding the nature of their relationship.
The late, great Kobe Bryant took a break from tearing up the court to have a date night with wife Vanessa Bryant at the 2008 MTV VMAs. They tied the knot in 2001 and were still going strong when he died in a helicopter crash in early 2020.
Controversial “Teen Mom 2” couple David Eason and Jenelle Evans attended the 2016 MTV VMAs together while she was pregnant with their daughter, Ensley, whom she delivered five months later in January 2017.
Long before he dated Amber Rose or married Kim Kardashian, Kanye West attended the 2007 MTV VMAs with his first great love: designer Alexis Phifer. The duo dated for six years and were even engaged for about a year and a half before they called it quits in early 2008.
How’s this for a random duo? Eva Longoria and Nelly posed together during the 2005 MTV VMAs and, in the process, sparked rumors they were dating. Although they arrived to the show together, it was never totally clear whether or not things between them were romantic.
Although they managed to avoid being photographed together during the 2019 MTV VMAs, Miley Cyrus and then-girlfriend Kaitlynn Carter made headlines when they were snapped holding hands while hitting up afterparties together following the award show, during which the former child star performed her hit ballad “Slide Away.” Multiple media outlets reported that the two women — who called off their whirlwind romance of just two months in September 2019 — were spied kissing and cuddling backstage during the VMAs.
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