Titanic stars Leonardo DiCaprio and Kate Winslet attend the Golden Globes
On the big screen, they were Jack and Rose. Oﬀscreen they looked like a couple of pasty kids on prom night.
On the big screen, they were Jack and Rose. Oﬀscreen they looked like a couple of pasty kids on prom night.
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.
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 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.
Sadly, they seem less like pop/movie stars in this photo and more like employees of a naughty-themed catering business.
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."
Even she is sick and tired of hearing “My Heart Will Go On,” and don’t think Wyclef doesn’t know it.
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.)
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.
The event was in February; in June, Demi and Bruce announced that they had split. Sad now ... Hey, look, it's Jack Nicholson!
The three movies gracing the marquee in the background just above Carson’s quasi-photobombing head: Hush, Dark City and U.S. Marshals.
He was just one Wes Anderson ﬁlm and six months away from being oﬃcially cool again.
Come to think of it, Carrie Mathison should wear more white turtlenecks.
When “smiling with your eyes” was still more of a “thousand-mile stare.”
Is that a bicycle seat in your unitard, Marilyn, or are you just … glad to see us?
Was it really 1998? Maybe it was 1993? Or 2009? Or last week? You never know with these two.
But if you need proof that time has passed, here you go. Sigh.
Worst poker face ever, Matt Damon. (Might explain why Rounders wasn’t exactly a hit.)
Following the lukewarm response to 1997’s Jackie Brown, Tarantino ventures out sporting a rare “Indiana Jones slacker” look.
Jonathan Lipnicki, former endearing movie star turned terrifying muscle man gives a thumbs-up on the red carpet.
Courtney in 1998: Celebrity Skin, celebrity friend.
The winner of the "look at the camera and smile" contest is ... Kate Moss.
Dweezil and Lisa looking totally ADORBS. And also exactly like two people just on a date, you know, to see The X-Files.
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-bellhop-newsboy? Me, too.
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.
Titanic inspired a brief foray into Edwardian-inspired dresses and embellishments, which was a great look for Kate Winslet …
… but maybe not so much for Fran Drescher, who apparently went nuts with the J. Peterman catalog.
As for Sandra Bullock, the Dowager Countess would have approved.
Even Diddy — then still good old Puff Daddy (or Puffy if you’re nasty) — got in on the retro action.
Sometimes, when you have no words, the stock photo caption is enough.
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.”
Nas, discussing the work he’d done since Illmatic.
Usher, who will always be our boo, gives us the ﬁnger the only way he knows how.
"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."
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.
She’s clearly alluding to the Cameron Diaz “hair gel” joke from the film.
What’s in Cameron’s hair this time? Oh, just two sharp sticks to stab the next person who asks her about “hair gel.”
”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?”
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.
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.
Who wanted to play “Bad Cop and Good Cowgirl,” hmm?
Is this a lost episode of My So-Called Life? Nope — it’s just that Leo looks like a tenth-grader here.
Even they looked older than Leonardo DiCaprio.
They’re laughing at the punchline to following joke: How many Kato Kaelins does it take to screw in a lightbulb? (Write your own!)
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.
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.
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!”
This image and the above description are so ’98 it actually hurts.
“We can stop doing this creepy dance stuﬀ soon, right? Come on, we made a whole movie of it. Can we stop soon? Please?”
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.
The one-time MTV VJ/freakshow wears his mom’s pantsuit while Ozzy demonstrates the only appropriate response.
Click! And then Paul Rudd dropped the ﬁlm oﬀ at a Rite Aid and waited ten days for the photos.
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.
In 1998, heavy modesty cloaks were worn in back for more wholesome twerking. It seems crazy now, but it really was a diﬀerent time.
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.
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.
Avert your eyes! Late-’90s Kabbalah Madonna’s on the loose!
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.
A second blue dress upstages the First Lady in 1998.
And with this picture of her inexplicably dancing with a Daffy Duck mascot, Drew Barrymore officially wins 1998.
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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