30 Celebrity Red Carpet Photos You Won’t Believe Are 20 Years Old

It’s hard to believe that it was almost 40 years ago that Prince was singing about partying like it’s 1999. And it may be even harder to grasp that 1999 was already two decades ago. The late ’90s brought us some famous fashion, hairstyles, and Hollywood couples that seem so outdated today. So, let’s look back at some celebrity photos from the late 1990s that show how far we’ve come. You won’t believe these pics are already 20 years-old.

Between the barrettes and the body glitter Jennifer Lopez sported at the 1998 MTV Movie Awards, she is the embodiment of late ’90s style. And considering how revealing it is, we should’ve seen her barely-there Versace dress at the 2000 Grammys coming!

If you’re a romantic comedy fan, you’re probably familiar with You’ve Got Mail, starring Meg Ryan and Tom Hanks. But you might not have realized the adored Nora Ephron movie is already over 20 years-old. Here are the stars, rocking head-to-toe black, at the 1998 New York City premiere.

While her husband was touting You’ve Got Mail, Rita Wilson was having her own red carpet moments. With fellow celebrities Sarah McLachlan and Faith Hill at the 1998 American Fashion Awards, it’s clear pink gowns, strappy sleeves, and even strappier sandals were all the rage two decades ago.

Mary-Kate And Ashley Olsen in black cardigans and blue and pink pencil skirts in 1999

The pencil skirts. The buttoned-up cardigans. The pearl chokers. The flipped blonde ‘dos. This photo of Mary-Kate and Ashley Olsen at the 1999 premiere of Anna and the King perfectly encapsulates pre-teen style from the era. Can you believe 20 years ago these famous twins were only 13?

Lenny Kravitz was at his peak in the late 1990s. “Fly Away” and “American Woman” dominated the charts and the rock star was everywhere, including at the 1998 Betsey Johnson fashion show. His western jacket, low-rise leather pants, and white sunglasses were considered fashionable 20 years ago.

Friends was one of the hottest TV shows at the turn of the century and it didn’t come any cooler than its stars. Here’s Courteney Cox looking pretty timeless and Jennifer Aniston in a handkerchief top and a very low-rise skirt at the 1999 Screen Actors Guild Awards. If this picture wasn’t late ’90s enough, check out those sparkles in the woman’s hair behind them. There was nothing that couldn’t be bedazzled 20 years ago.

Here are “it girls” Gwyneth Paltrow and Kate Moss embracing backstage at the 1998 Calvin Klein fashion show. Paltrow’s tinted sunglasses pushed back atop her shoulder-length hair just screams late 1990s.

Eminem in white t-shirt at 1999 Source Awards

It’s hard to believe that 21 years ago, M&M’s were just a candy. That all changed in 1999, when Eminem—pictured here at the Source Awards—started dominating the music scene. His major label debut, The Slim Shady LP, was released that year and every ’90s kid was trying to learn the words to “My Name Is…”

Even though she’s only in her thirties, Scarlett Johansson has been a mainstay in Hollywood for more than 20 years. Here she is in 1998, sitting front row at a fashion show. With her spaghetti strap tank top and metallic nail polish, she’s just like any other 14 year-old.

It’s hard to remember there was a time when Kate Winslet wasn’t at the Oscars. But in 1998, she made her debut at Hollywood’s biggest night when she was nominated for Best Actress for her epic performance in Titanic. Winslet’s velvet green and gold dress was just the start of her red carpet dominance.

The couple that dresses together, stays together. Here are Jada Pinkett Smith and Will Smith in matching white Gucci suits and black shoes at the 1998 Essence Awards. This was taken just a few months before their son, Jaden Smith, was born.

We cannot get over the perfectly shiny late ’90s bracelets and tops in this photo of Melissa Joan Hart and Britney Spears at the 1999 premiere of the teen movie Drive Me Crazy. Hart’s hair twists and Spears’ chain purse really take it to new 1990s levels (as does the camcorder being used behind them).

If you couldn’t see what was in someone’s purse at the turn of the century, they probably weren’t fashionable. Exhibit A: Halle Berry, who paired her beaded bag with a floral skirt and spaghetti strap tank at the 1998 Lilith Fair concert. This was just before she solidified herself as a force to be reckoned with in Hollywood, thanks to her role in the 1999 HBO biopic Introducing Dorothy Dandridge.

Cameron Diaz donned this formerly fashionable denim bucket hat to the 2000 premiere of Requiem for a Dream. Let us hope this look never becomes stylish again.

Celebrities Natalie Portman and Liam Neeson at 1999 Star Wars Phantom Menace Event

Two decades after the original series premiered and nearly two decades before J.J. Abrams brought it back again, Star Wars Episode I: The Phantom Menace made its debut in 1999. Here, stars Natalie Portman and Liam Neeson promote the movie, before the backlash set in.

Part of the fun of these photos is the defunct technology in the background. Look at the hefty camcorder one cameraman is using to capture Salma Hayek in her crushed velvet glory at the 1998 VH1 Fashion Awards.

At the 1998 MTV Video Music Awards, Diddy was still known as Puff Daddy. That’s how old this photo of the rapper is. Here is the artist formerly known as Puffy holding his moon man for the Viewer’s Choice category for his song “It’s All About the Benjamins.”

Everything about this photo captures the glory of 1999. 1) Fergie was still being called Stacey Ferguson. 2) She was a member of a now-defunct pop group called Wild Orchid. 3) Her cowboy hat. 4) Her frosted lipstick. 5) Her fur-trimmed jewel-toned jacket. 6) It was taken at the 1999 Blockbuster Awards. (RIP, Blockbuster.)

Gwen Stefani and Courtney Love were the queens of alternative style in the 1990s. Between Stefani’s braids and ombre skirt and Love’s flower crown and fuzzy shoes, their 1998 Grammys looks are what the era was all about.

Before she was winning Oscars or starring in blockbuster hits, Charlize Theron was building her resume with small roles in films like That Thing You Do! and Celebrity. Here she is in a lingerie-exposed dress at the 1998 premiere of the latter—five years before Monster and more than 15 years before Max Max: Fury Road.

At the 2000 Grammys, TLC’s Left Eye, T-Boz, and Chili went minimal in terms of color and also fabric.

If you weren’t wearing a floor-length gown with a matching shawl and holding a purse that could only fit a Nokia cell phone, you were doing formal attire wrong in the late 1990s. With that said, Winona Ryder—pictured here at the premiere of Celebrity in 1998—knew what was up.

It doesn’t get cuter than this photo from the premiere of One Fine Day, a romantic comedy that starred Michelle Pfeiffer and George Clooney as single parents (with Alex D. Linz and Mae Whitman playing their children respectively). Even decades before he had babies of his own, Clooney had a way with kids.

1999 was the year people started taking Jim Carrey seriously, thanks to his turns in The Truman Show and Man on the Moon. Here he is with his first Golden Globe, which he earned for the former.

For comparison, Carrey is now a grandfather and he’s being nominated for Golden Globes for playing a children’s TV host who’s been working for 30 years.

It’s hard to imagine now, but in the late 1990s, Sandra Bullock and Matthew McConaughey dated for two years. Here they are at the 1998 Teen Choice Awards, where she won for “Choice Hissy Fit” for her performance in Forces of Nature, and he was up for “Choice Movie Love Scene” with Elizabeth Hurley for EdTV. (If you’ve forgotten about both of those movies, you’re forgiven.)

There was no fashion icon bigger than the fictional Carrie Bradshaw of Sex and the City at the turn of the century. And yet, this is what Sarah Jessica Parker, the woman who played her, wore to the premiere of the HBO TV show in 1998. Times certainly have changed.

Cate Blanchett and Hilary Swank starred together in the 2000 supernatural thriller The Gift, which you wouldn’t be wrong to have forgotten either.

While Blanchett’s look for the premiere is timeless, Swank’s could not be more trendy. With her feathered purse, her matching top and duster, and her silky trousers, she’s living her best late ’90s life.

One of TV’s most beloved matriarchs, Patricia Heaton, got her big break on Everybody Loves Raymond in 1996. In 1999, she earned her first Emmy nomination and this late ’90s Bohemian-inspired look is what she wore to the awards show. We do not miss the days of blue eyeshadow.

Long before she was on Veep, Anna Chlumsky was a beloved child actress, most notably for her performances in My Girl and its sequel. At the Youth in Film Awards in 1993, she wore an oh-so-’90s floral dress and peace sign necklace. It doesn’t get more classic 13-year-old 1990s girl than that.

Here’s another couple from the late 1990s you probably forgot about: Ashley Judd and Michael Bolton. She starred in his music video for “The Best of Love” and here they are at the CableACE Awards, which was the cable counterpart for the Emmys for a mere three years until the Emmys finally included cable TV shows. And for a look back at TV shows that are gone but not forgotten, here are The 50 Best One-Season TV Shows in Television History.

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