The VMAs may look a little different tonight with a global pandemic unfolding around us, but if all goes well, in 20-plus years we should be able to look back on those pictures and think, “What the heck were we all thinking?” And for more on the VMAs, check out these 20 Shocking Facts About the MTV VMAs You Definitely Never Knew.
1 Nothing could make Eminem happy.
Eminem won Best New Artist at the 1999 VMAs, but still made this face. And for more on ’90s hits, check out 20 Hit Songs You Won’t Believe Are Turning 20 This Year.
2 Pamela Anderson wore exclusively statement pieces…
Pamela Anderson’s outfit did not disappoint. From her sequin, asymmetrical pants to her Victorian corset to her fluffy pink hat and electric blue eyeshadow, this has to be one of the all-time best award show outfits.
3 …Leaving none for Natalie Portman.
And because the VMAs are nothing if not a study in extremes, here’s Natalie Portman, looking like she’s attending the opera. The 18-year-old actress was just beginning her freshman year at Harvard after starring in Star Wars: Episode I. And for more on Portman, check out 50 Celebrities Whose Real Names You Never Knew.
4 Britney Spears wore a very shiny outfit.
Before performing her debut mega-hit “Baby One More Time,” Britney Spears served us this classic ’90s ensemble, with metallic snakeskin pants, a long sleeve metallic crop top, and an over the top choker.
5 Aaliyah looked timelessly fashionable.
The iconic, late R&B singer Aaliyah looked stunning as always in a black mesh top and mini sunglasses while heading into the VMAs. There’s a reason this exact look is still being emulated today. And for more on Aaliyah, check out 15 Celebrities Who Got Their Start on “Star Search.”
6 Wyclef Jean went to prom.
Sometime between the breakup of The Fugees and attempting to become the president of Haiti, Wyclef Jean came to the VMAs dressed for the prom. If you look closely, his matching vest and tie featured metallic dragons. Classic 1999!
7 Lauryn Hill was at the top of her game.
The Miseducation of Lauryn Hill came out just one year earlier, and L Boogie was on top of the world. She took home four moonmen, yet Paul McCartney inexplicably introduced her as “some guy called Lawrence Hill.” And for more on the ’90s, check out these 30 Facts That Will Overwhelm You With 1990s Nostalgia.
8 Rene Zellweger rolled out of bed to present awards.
Looking like a true 1990s icon, Rene Zellweger crimped half of her hair and turned up to the VMAs in a nightgown. Obviously, she had us at “hello.”
9 Sugar Ray shaved selectively.
The band Sugar Ray was a “what not to wear” of facial hair at the VMAs in 1999: their signature goatees, chin straps and soul patches were on proud display. And for more on ’90s music, check out 50 Things Only People Who Lived in the ’90s Will Remember.
10 Limp Bizkit was there, but unsure about it.
Limp Bizkit also brought their facial hair A-game, and of course Fred Durst wore his signature uniform of a t-shirt and backwards baseball hat to The Metropolitan Opera House. Wes Borland looked terrified to be there.
11 Tyrese wore a costume.
Model and singer Tyrese came to the 1999 VMAs ready for battle, but stayed for the festivities. His special ops-inspired outfit included some fingerless gloves and a walkie talkie. And for more on ’90s fashion, check out the 25 Things Cool People Wore in the 1990s.
12 Diana Ross stole the show.
Diva Diana Ross had a notorious moment with a very scantily clad Lil’ Kim while presenting at the 1999 awards show. Luckily, Kim was unfazed, later saying in an interview that she took it as a “friendly” thing.
13 Steven Tyler and Run-D.M.C. struck a power pose.
Aerosmith and Run-D.M.C. had just remade “Walk This Way” and the world was their oyster, so Steven Tyler dressed as a mermaid, naturally. And for more ’90s nostalgia, check out these 30 Gifts That Prove the ’90s Were the Best.
14 Will and Jada wore an entire cow.
Forever power couple Will Smith and Jada Pinkett Smith, who literally never age a day, showed up looking exactly the way they do now in 2020, except with more cow hide. Will won Best Video for “Welcome to Miami,” which is still a bop.
15 Heather Locklear wore a scarf, but forgot where to put it.
Heather Locklear came to the 1999 VMAs wearing a scarf as a shirt, as people used to do back then. She looks very happy with her then-husband Richie Sambora, the guitarist from Bon Jovi. And for more on former A-list couples, check out 15 Celebrity Couple Breakups You’re Probably Still Mourning.ae0fcc31ae342fd3a1346ebb1f342fcb
16 Christina Aguilera was very Christina Aguilera.
Christina Aguilera encapsulated a whole era in a single outfit: so much cheetah print, such very square-toed shoes, such absolutely bonkers eyeshadow. There is nothing not to like about this photo.
17 J. Lo and Puff Daddy looked cute together.
It-couple of yesteryear Jennifer Lopez and Puff Daddy shared a sweet moment after the awards show. This feels like a lifetime ago, yet somehow J. Lo hasn’t aged a day. And for more on the complicated web of celebrity relationships, check out these 60 Celebrity Couples Who Share an Ex.
18 Jay-Z appeared solo, just before meeting Beyonce.
Baby-faced Jay-Z hadn’t yet met Beyonce when this photo was taken, which explains why he’s looking so cheerless, even after winning an award. Don’t worry, Jay, she’s coming!
19 Ricky Martin was Livin’ la Vida Loca.
Adorable Ricky Martin looked thrilled to have won two VMA awards in 1999. He wore a very sensible sweater and the pants of a bellhop. And for more ’90s celebrity news, This Is What Nicole Kidman and Tom Cruise’s Kids Together Look Like Now.
