The Most 1998 Celebrity Pics Ever
Just as we launched our weeklong series looking back at fame in 1998 with a celebrity slideshow, so it is decreed by Internet law that we must book-end our coverage with yet another celebrity slideshow. So join us as we bid adieu to the outrageous year that gave us Titanic mania, TRL, the Beek, and so much more with this sprawling collection of pictures designed to make you say, “That’s so 1998.” Or “I’m so old.” Either way, enjoy!
On the big screen, they were Jack and Rose. Offscreen they looked like a couple of pasty kids on prom night.
Photo: Brenda Chase
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 a...
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.
Photo: HAL GARB
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...
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."
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 waitr...
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?"
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.
Ph...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.
Photo: Ron Galella, Ltd./1998 Ron Galella, Ltd.
Sadly, they seem less like pop/movie stars in this photo and more like employees of a naughty-themed catering business.
Photo: Ron Galella, Ltd./1998...Sadly, they seem less like pop/movie stars in this photo and more like employees of a naughty-themed catering business.
Photo: Ron Galella, Ltd./1998 Ron Galella, Ltd.
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...
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."
Photo: JOYCE NALTCHAYAN
Even she is sick and tired of hearing “My Heart Will Go On,” and don’t think Wyclef doesn’t know it.
Photo: KMazur
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.)
Photo: ...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.)
Photo: Ron Galella, Ltd./1998 Ron Galella, Ltd.
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 w...
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.
Photo: Kevin Mazur
The event was in February; in June, Demi and Bruce announced that they had split. Sad now ... Hey, look, it's Jack Nicholson!
Photo: New York D...The event was in February; in June, Demi and Bruce announced that they had split. Sad now ... Hey, look, it's Jack Nicholson!
Photo: New York Daily News Archive/1998/Daily News, L.P. (New York)
The three movies gracing the marquee in the background just above Carson’s quasi-photobombing head: Hush, Dark City and U.S. Marshals.
Photo: Marion...The three movies gracing the marquee in the background just above Carson’s quasi-photobombing head: Hush, Dark City and U.S. Marshals.
Photo: Marion Curtis/Time Life Pictures
He was just one Wes Anderson film and six months away from being officially cool again.
Photo: Ron Galella, Ltd.
Come to think of it, Carrie Mathison should wear more white turtlenecks.
Photo: Ron Galella
When “smiling with your eyes” was still more of a “thousand-mile stare.”
Photo: S. Granitz
Is that a bicycle seat in your unitard, Marilyn, or are you just … glad to see us?
Photo: Frank Micelotta
Was it really 1998? Maybe it was 1993? Or 2009? Or last week? You never know with these two.
Photo: Jeff Kravitz/@2005 Jeff Kravitz/FilmMagic.com
But if you need proof that time has passed, here you go. Sigh.
Photo: Barry King
Worst poker face ever, Matt Damon. (Might explain why Rounders wasn’t exactly a hit.)
Photo: David Waite
Following the lukewarm response to 1997’s Jackie Brown, Tarantino ventures out sporting a rare “Indiana Jones slacker” look.
Photo: Dan Callister
Jonathan Lipnicki, former endearing movie star turned terrifying muscle man gives a thumbs-up on the red carpet.
Photo: Ron Galella
Courtney in 1998: Celebrity Skin, celebrity friend.
Photo: S. Granitz
The winner of the "look at the camera and smile" contest is ... Kate Moss.
Photo: Ron Galella, Ltd./1998 Ron Galella, Ltd.
Dweezil and Lisa looking totally ADORBS. And also exactly like two people just on a date, you know, to see The X-Files.
Photo: S. Granitz
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 ...
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.
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-bel...
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.
Photo: Ron Galella
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 ...
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.
Photo: Michael Okoniewski
Titanic inspired a brief foray into Edwardian-inspired dresses and embellishments, which was a great look for Kate Winslet …
Photo: Jim Smeal
… but maybe not so much for Fran Drescher, who apparently went nuts with the J. Peterman catalog.
Photo: Ron Galella
As for Sandra Bullock, the Dowager Countess would have approved.
Photo: Jim Smeal
Even Diddy — then still good old Puff Daddy (or Puffy if you’re nasty) — got in on the retro action.
Photo: Ron Galella
Sometimes, when you have no words, the stock photo caption is enough.
Photo: Vince Bucci
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.”
Photo: Kevin Maz...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.”
Photo: Kevin Mazur
Nas, discussing the work he’d done since Illmatic.
Photo: Jeff Kravitz/all rights reserved www.filmmagic.com
Usher, who will always be our boo, gives us the finger the only way he knows how.
Photo: Brenda Chase
"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...
"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."
Photo: Jeff Kravitz
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 ...
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.
Photo: Kevin.Mazur
She’s clearly alluding to the Cameron Diaz “hair gel” joke from the film.
Photo: Jim Smeal
What’s in Cameron’s hair this time? Oh, just two sharp sticks to stab the next person who asks her about “hair gel.”
Photo: Kevin.Mazur
”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 fro...
”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?”
Photo: Mirek Towski/Time Life Pictures
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.
...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.
Photo: S. Granitz
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...
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.
Photo: Evan Agostini
Who wanted to play “Bad Cop and Good Cowgirl,” hmm?
Photo: Jim Smeal
Is this a lost episode of My So-Called Life? Nope — it’s just that Leo looks like a tenth-grader here.
Photo: Kevin.Mazur
Even they looked older than Leonardo DiCaprio.
Photo: New York Daily News Archive/1998/Daily News, L.P. (New York)
They’re laughing at the punchline to following joke: How many Kato Kaelins does it take to screw in a lightbulb? (Write your own!)
Photo: Barry King
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.
Pho...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.
Photo: Ron Galella
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...
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.
Photo: Ron Galella
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 —...
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!”
Photo: Ron Galella
Random much?
Photo: New York Daily News Archive/1998/Daily News, L.P. (New York)
This image and the above description are so ’98 it actually hurts.
Photo: Jeff Kravitz/@2005 Jeff Kravitz/FilmMagic.com
“We can stop doing this creepy dance stuff soon, right? Come on, we made a whole movie of it. Can we stop soon? Please?”
Photo: Evan Agostini
Politically Incorrect had been picked up by ABC the year before, providing a lively bipartisan forum for discussing current events. More importantly, ...
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.
Photo: Jim Smeal
The one-time MTV VJ/freakshow wears his mom’s pantsuit while Ozzy demonstrates the only appropriate response.
Photo: Time & Life Pictures/Time & Lif...The one-time MTV VJ/freakshow wears his mom’s pantsuit while Ozzy demonstrates the only appropriate response.
Photo: Time & Life Pictures/Time & Life Pictures
Click! And then Paul Rudd dropped the film off at a Rite Aid and waited ten days for the photos.
Photo: Time & Life Pictures/Time & Life Pictures
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 ...
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.
Photo: Kevin.Mazur
In 1998, heavy modesty cloaks were worn in back for more wholesome twerking. It seems crazy now, but it really was a different time.
Photo: Jeffrey Mayer
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...
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.
Photo: Ron Galella/1998 Ron Galella, Ltd.
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 i...
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.
Photo: SGranitz
Avert your eyes! Late-’90s Kabbalah Madonna’s on the loose!
Photo: Jeff Kravitz/@2005 Jeff Kravitz/FilmMagic.com
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 sudd...
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.
Photo: Ron Galella
A second blue dress upstages the First Lady in 1998.
Photo: New York Daily News Archive/1998/Daily News, L.P. (New York)
And with this picture of her inexplicably dancing with a Daffy Duck mascot, Drew Barrymore officially wins 1998.
Photo: Jim Smeal
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? T...
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!
Photo: Splash News/? www.splashnews.com