The Most 1998 Celebrity Pics Ever
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That's So 1998

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Titanic stars Leonardo DiCaprio and Kate Winslet attend the Golden Globes

Photo: Hulton Archive

On the big screen, they were Jack and Rose. Offscreen they looked like a couple of pasty kids on prom night.

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Ben Affleck and Matt Damon brandish their Golden Globes

Photo: AFP

On the bromance front, it was a big year for Matt Damon and Ben Affleck. Even though Good Will Hunting won only a few of its dozen or so Academy Award and Golden Globe nominations, they really seemed to be winning at life. Obligatory "How do you like them apples?" reference here.

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Minnie Driver at the Golden Globe Awards (right) and at Vanity Fair’s Oscar party (left)

Photo: Hulton Archive, Ron Galella Collection

Just days before the photo on the right was taken, Driver, who got an Oscar nomination for her supporting role in Good Will Hunting, had been publicly dumped by her boyfriend and co-star Matt Damon — when he’d mentioned during an Oprah interview that he was single. She managed to pull off a polished (if slightly dull) appearance at the Golden Globes. But once she’d had time to plan, she turned up at the Oscars wearing the red Halston on the left, which her stylist called “the screw-you dress."

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Sarah Michelle Gellar hits the MTV Video Music Awards with Alyson Hannigan (left) and the Spice World movie premiere after-party with Seth Green (right)

Photo: WireImage, Hulton Archive

TV’s Willow and Buffy know that “up-dos” were the hairstyles of choice in the late-’90s, even though they made everyone look like truck stop waitresses. And TV’s Oz’s face says, "Remember the second season of Buffy the Vampire Slayer, when a hellmouth called Spice World opened up in movie theatres?"

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Mary-Kate and Ashley Olsen wave at the Spice World premiere

Photo: Ron Galella Collection

By 1998, the Olsen twins had their own successful production company, so it’s only natural that they looked and dressed like tiny talk-show hosts.

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Spice Girls dramatically gather at the premiere of Spice World

Photo: Ron Galella Collection

Sadly, they seem less like pop/movie stars in this photo and more like employees of a naughty-themed catering business.

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Harrison Ford and British Prime Minister Tony Blair with President Clinton at a state dinner at the White House

Photo: AFP/Getty Images

Bill was just ten days removed from having uttered the immortal line, "I did not have sex with that woman Miss Lewinsky." Tony was ten hours removed from having practiced that fake smile in the mirror. And Harrison was ten minutes removed from having tickled Buddy the dog while saying, "Laugh it up, fuzzball."

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Wyclef Jean and Celine Dion at the Grammys

Photo: WireImage

Even she is sick and tired of hearing “My Heart Will Go On,” and don’t think Wyclef doesn’t know it.

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Gavin Rossdale and Gwen Stefani at a Grammy Awards pre-party

Photo: Ron Galella Collection

Hey, here’s someone else we can blame for Miley Cyrus’s Grammy performance look! (Nice try, Gwen, but pointing at Gavin isn't going to work.)

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Bob Dylan performs at the Grammys alongside stage-crasher “Soy Bomb” (Michael Portnoy)

Photo: WireImage

Never mind Elton and Eminem or Paul McCartney and Linkin Park and Jay-Z: the best multi-artist mash-up performance ever to grace the Grammy telecast was that of Messrs. Dylan and Bomb.

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Demi Moore, Jack Nicholson and Bruce Willis at a fundraiser in New York

Photo: New York Daily News

The event was in February; in June, Demi and Bruce announced that they had split. Sad now ... Hey, look, it's Jack Nicholson!

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Matthew McConaughey, Carson Daly and Richard Linklater in New York.

Photo: Time & Life Pictures

The three movies gracing the marquee in the background just above Carson’s quasi-photobombing head: Hush, Dark City and U.S. Marshals.

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Bill Murray wears yellow goggle-shades at the Wild Things premiere

Photo: Ron Galella Collection

He was just one Wes Anderson film and six months away from being officially cool again.

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Uma Thurman, Claire Danes and Liam Neeson at the premiere of  Les Misérables

Photo: WireImage

Come to think of it, Carrie Mathison should wear more white turtlenecks.

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Tyra Banks arrives at Vanity Fair’s Oscar party

Photo: Hulton Archive

When “smiling with your eyes” was still more of a “thousand-mile stare.”

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Marilyn Manson performs at the MTV Video Music Awards

Photo: Hulton Archive

Is that a bicycle seat in your unitard, Marilyn, or are you just … glad to see us?

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Billie Joe Armstrong and Winona Ryder at the MTV Video Music Awards

Photo: FilmMagic, Inc

Was it really 1998? Maybe it was 1993? Or 2009? Or last week? You never know with these two.

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Lindsay Lohan at the premiere of The Parent Trap

Photo: Hulton Archive

But if you need proof that time has passed, here you go. Sigh.

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Matt Damon plays cards at the World Series of Poker

Photo: Hulton Archive

Worst poker face ever, Matt Damon. (Might explain why Rounders wasn’t exactly a hit.)

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Quentin Tarantino attends the Pecker premiere

Photo: Hulton Archive

Following the lukewarm response to 1997’s Jackie Brown, Tarantino ventures out sporting a rare “Indiana Jones slacker” look.

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Jerry Maguire star Jonathan Lipnicki at a black-tie event in Los Angeles

Photo: Ron Galella Collection

Jonathan Lipnicki, former endearing movie star turned terrifying muscle man gives a thumbs-up on the red carpet.

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Courtney Love and Drew Barrymore at the premiere of Home Fries

Photo: WireImage

Courtney in 1998: Celebrity Skin, celebrity friend.

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Gwyneth Paltrow, Kate Moss and Liv Tyler at a Beck concert in New York

Photo: WireImage

The winner of the "look at the camera and smile" contest is ... Kate Moss.

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Dweezil Zappa and Lisa Loeb attend The X-Files premiere

Photo: WireImage

Dweezil and Lisa looking totally ADORBS. And also exactly like two people just on a date, you know, to see The X-Files.

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Jennifer Lopez at the Grammys (left) and the VH1 Fashion Awards (right)

Photo: WireImage, Ron Galella Collection

Little-known fact about “Jenny from the Block”: Before she wore priceless Versace gowns, J.Lo had to knit her own dresses for the Grammys (left). And if all that gray combed-over hair (right) were on any other surface besides J. Lo it would look horrifying, but she pulls it off nicely.

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David Arquette and Courteney Cox at the Snake Eyes premiere

Photo: Ron Galella Collection

He became legitimately stylish later and even started his own clothing line, but don't you miss the days when David Arquette dressed like a jockey-bellhop-newsboy? Me, too.

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Shania Twain performs at the New York State Fair

Photo: Hulton Archive

The 1990s were the decade of the Canadian diva, and Shania, with her cheesily cheerful single “Man I Feel Like a Woman” was the one we most wanted to drink rum and Cokes with. Okay, we still do.

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Kate Winslet smiles on the red carpet at the Academy Awards

Photo: Ron Galella Collection

Titanic inspired a brief foray into Edwardian-inspired dresses and embellishments, which was a great look for Kate Winslet …

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Fran Drescher twirls at the Titanic premiere

Photo: Ron Galella Collection

… but maybe not so much for Fran Drescher, who apparently went nuts with the J. Peterman catalog.

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Sandra Bullock at the Golden Globes

Photo: Ron Galella Collection

As for Sandra Bullock, the Dowager Countess would have approved.

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Sean “Puffy” Combs at the Grammys

Photo: Ron Galella Collection

Even Diddy — then still good old Puff Daddy (or Puffy if you’re nasty) — got in on the retro action.

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“Academy Award–winning Robin Williams wears a clown nose as he places his hands in cement during his hand and footprint ceremony outside Mann's Chinese Theatre. Williams is currently starring in the critically acclaimed film Patch Adams, about a doctor who uses humor to help heal his patients.”

Photo: AFP

Sometimes, when you have no words, the stock photo caption is enough.

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Paula Cole at the Grammy Awards

Photo: WireImage

Paula Cole offers a salty salute to the future world that would remember her only as “that chick who sang the Dawson’s Creek theme.”

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Nas at an MTV Video Music Awards after-party

Photo: FilmMagic, Inc

Nas, discussing the work he’d done since Illmatic.

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Usher at the 1998 MTV Video Music Awards

Photo: Hulton Archive

Usher, who will always be our boo, gives us the finger the only way he knows how.

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Geena Davis and Susan Sarandon at the Academy Awards

Photo: FilmMagic, Inc

"Thelma and Louise came out seven years ago, but we’d just like to remind you that there still aren’t enough strong female protagonists in movies. I mean, Spice World? Jesus."

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Jeff Townes and Will Smith (aka DJ Jazzy Jeff and the Fresh Prince) at the Grammys

Photo: WireImage

When Smith’s contribution to the Men in Black soundtrack won the Grammy for Best Rap Solo Peformance, Will Smith and his producer pal Jazzy dedicated their awards to Tupac and Biggie.

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Kathy Griffin at the There's Something About Mary premiere

Photo: Ron Galella Collection

She’s clearly alluding to the Cameron Diaz “hair gel” joke from the film.

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Cameron Diaz at the GQ Men of the Year awards

Photo: WireImage

What’s in Cameron’s hair this time? Oh, just two sharp sticks to stab the next person who asks her about “hair gel.”

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Magic Johnson and Sean “Puffy” Combs at the Rush Hour premiere

Photo: Time & Life Pictures

”Puffy! Mr. Hit-maker! If I cling to you for dear life, will it bring my ill-fated and extremely terrible syndicated talk show The Magic Hour back from the dead?”

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Drew Barrymore poses at the Academy Awards

Photo: WireImage

So what if her look was more “rave” than “red carpet.” Drew was 23, had her own production company, and she hadn’t gotten together with Tom Green yet.

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Gwyneth Paltrow at the Shakespeare in Love premiere

Photo: Hulton Archive

A few months before her Oscar win for Shakespeare in Love, Paltrow test-drives all her signature looks — the demure smirk, the braless dress, the hair center-parted with terrifying precision.

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Mark Wahlberg and Jennifer Lopez at the MTV Video Music Awards

Photo: Ron Galella Collection

Who wanted to play “Bad Cop and Good Cowgirl,” hmm?

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Claire Danes and Leonardo DiCaprio at The Man in the Iron Mask premiere

Photo: WireImage

Is this a lost episode of My So-Called Life? Nope — it’s just that Leo looks like a tenth-grader here.

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Hanson arrives at the Grammy Awards

Photo: New York Daily News

Even they looked older than Leonardo DiCaprio.

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Trey Parker, Kato Kaelin, and Matt Stone at the BASEketball premiere

Photo: Getty Images

They’re laughing at the punchline to following joke: How many Kato Kaelins does it take to screw in a lightbulb? (Write your own!)

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Breckin Meyer gazes at the BASEketball premiere

Photo: Ron Galella Collection

No offense, Matt and Trey, but the stoner dude from Clueless ironically wearing a Debbie Gibson T-shirt was the best thing anyone saw that night.

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The Goo Goo Dolls pose at the 1998 MTV Video Music Awards

Photo: Ron Galella Collection

The cow-print fin that appeared to be coming out of Johnny Rzeznik’s head was just an illusion. His “playfully” tousled alterna-mullet, though, was all too real.

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Jenna Elfman and Tom Cruise at the premiere of Without Limits

Photo: WireImage

Apparently the secret Scientologist handshake is a two-handed vise grip paired with a potent stare that says, ”Two-handed vise grip and potent stare — go!”

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New York City mayor Rudy Giuliani and singer Mariah Carey at a New York City event promoting an adoption fair

Photo: New York Daily News

Random much?

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Lenny Kravitz and Gwen Stefani buddy up at an MTV Video Music Awards after-party

Photo: FilmMagic, Inc

This image and the above description are so ’98 it actually hurts.

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Will Ferrell and Chris Kattan at the A Night at the Roxbury premiere

Photo: Hulton Archive

“We can stop doing this creepy dance stuff soon, right? Come on, we made a whole movie of it. Can we stop soon? Please?”

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Bill Maher and a guest hit the premiere of Out of Sight

Photo: Ron Galella Collection

Politically Incorrect had been picked up by ABC the year before, providing a lively bipartisan forum for discussing current events. More importantly, it provided Bill Maher with a reason to wear something nicer than over-sized paisley silk shirts.

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Ozzy Osbourne and Jesse Camp meet and greet in August

Photo: Time & Life Pictures

The one-time MTV VJ/freakshow wears his mom’s pantsuit while Ozzy demonstrates the only appropriate response.

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Paul Rudd snaps a pic at a screening of The Object of My Affection

Photo: Time & Life Pictures

Click! And then Paul Rudd dropped the film off at a Rite Aid and waited ten days for the photos.

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Katie Holmes at the Emmys

Photo: WireImage

Before Tom Cruise, before Suri, before she became a fashion icon, Katie Holmes went to awards shows looking like the junior bridesmaid at your cousin Debbie’s wedding.

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Brandy at the MTV Video Music Awards

Photo: WireImage

In 1998, heavy modesty cloaks were worn in back for more wholesome twerking. It seems crazy now, but it really was a different time.

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Cher attends the Academy Awards

Photo: Ron Galella Collection

A nice change from the usual spangled-body-stocking getups that Bob Mackie designed for Cher at previous Oscars, this flesh-colored dress was like sexy macramé.

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Backstreet Boys chillax at the Chateau Marmont

Photo: WireImage

Huge white coats were clearly having a moment. And billowy white pants. On windy days in 1998, the Backstreet Boys looked like a five-masted schooner in full sail.

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Madonna, Guy Oseary and Ben Stiller at an MTV Video Music Awards after-party

Photo: FilmMagic, Inc.

Avert your eyes! Late-’90s Kabbalah Madonna’s on the loose!

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Meg Ryan, Nora Ephron and Tom Hanks huddle at the You've Got Mail premiere

Photo: Ron Galella Collection

Promoting one of her last romantic comedies, Meg Ryan dons a long black coat and looks ahead to perhaps being cast in The Matrix, while Tom Hanks suddenly realizes that Amazon.com will render the plot of You’ve Got Mail irrelevant in the next ten years.

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Gwyneth Paltrow and Hillary Clinton at the Shakespeare in Love premiere

Photo: New York Daily News

A second blue dress upstages the First Lady in 1998.

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Drew Barrymore at the “A Time for Heroes” AIDS benefit

Photo: WireImage

And with this picture of her inexplicably dancing with a Daffy Duck mascot, Drew Barrymore officially wins 1998.

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Kevin Connolly and Leonardo DiCaprio with Michael Jackson at a tepee party at Neverland Ranch

Photo: Splash News

You had to know that Leo and Jacko clowning at a Neverland Ranch tepee party was how our weeklong look back at fame in 1998 was going to end, right? Thanks for stopping by!

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