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24 Celeb Red Carpet Photos From 1990s You Have to See to Believe

From the couples we miss to the fashion trends we definitely don't...

Thirty years ago, streaming services, prestige TV, and umpteen more movies about Batman were still in the distant future. But some things haven't changed in three decades. In 1990, celebrities were still doing their thing on the red carpet: posing together, debuting new relationships, and testing the limits of fashion. You may remember 1990 like it was yesterday, but we bet some of these captured Hollywood moments will surprise you. Page through 24 of our favorite celeb red carpet photos from 1990 and be thankful that black, sheer pantyhose are a trend of the past. And for snaps from the beginning of the millennium, here are 23 Celeb Red Carpet Photos From 2000 You Have to See to Believe.

Brooke Shields and Macaulay Culkin bonded.

Brooke Shields and Macaulay Culkin
John Barrett/ Stock Photo

Brooke Shields became a child star when she was 12 years old, so she could certainly relate to Home Alone star Macaulay Culkin. The two hung out at a Toys for Tots benefit in 1990, the year that his blockbuster hit theaters. And for more stars who started early, here are 15 Celebrity Kids Who Are All Grown Up Now.

Mr. T dressed to the nines.

Mr T
Barry King/Alamy Stock Photo

Actor and wrestler Mr. T's signature flamboyant style was on full display at the 1990 premiere of the Arnold Schwarzenegger flick Total Recall. Check out those matching cowboy boots!

Dennis Quaid and Meg Ryan had a date night.

Dennis Quaid and Meg Ryan
Barry King/Alamy Stock Photo

Dennis Quaid brought along his future wife Meg Ryan to the premiere of his 1990 film Postcards From the Edge. They went on to marry in 1991 and separate in 2000. For more pairs we miss, here are 15 Celebrity Couple Breakups You're Probably Still Mourning.

Fred Savage was in the passenger seat.

Fred Savage 1990
Barry King/Alamy Stock Photon

Obviously, a 14-year-old Fred Savage wouldn't have been able to drive himself to a party in 1990. But he was already two years into his run on The Wonder Years and probably didn't even have to call "shotgun."

Drew Barrymore and Grace Jones posed like their lives depended on it.

Drew Barrymore and Grace Jones
John Barrett/ Stock Photo

Meanwhile, a 15-year-old Drew Barrymore hung out with model and singer Grace Jones at a bash thrown in her honor at Limelight Disco in New York. And for some juicy (if disproven) Hollywood gossip, check out 50 Totally Absurd Celeb Rumors That Some People Really Believe.

Christian Slater came prepared for a snooze.

Christian Slater
Barry King/Alamy Stock Photo

What statement was Pump Up the Volume star Christian Slater trying to make with the ensemble he wore to the 1990 premiere of Martin Scorcese's Goodfellas? That he was planning to nap through it?

Emily Lloyd and Adrian Pasdar goofed around.

Adrian Pasdar and Emily Lloyd
Barry King/Alamy Stock Photo

Actress Emily Lloyd manhandled her costar from 1989's Cookie, Adrian Pasdar, when they attended the premiere of the 1990 thriller Pacific Heights. In 2020, however, Pasdar is known mostly for being the ex-husband of The Chicks lead singer, Natalie Maines—and for leaving someone else's tights on her boat. For more famous folks who've split up with the same people, here are 60 Celebrities Who Share an Ex.

Jason Priestley and Shannen Doherty were teen dreams.

Jason Priestley and Shannen Doherty
John Barrett/ Stock Photo

Beverly Hills, 90210 costars Jason Priestley and Shannen Doherty dated while they were working on the show, which thrilled fans. It didn't last, but they look perfectly matched at an event in 1990.

Sidney Poitier and Morgan Freeman shared mutual respect.

Sidney Poitier and Morgan Freeman
Adam Scull/Alamy Stock Photo

Morgan Freeman and Sidney Portier have been friends for years, with the former frequently citing the latter as one of his heroes. Here they are together at the 1990 National Board of Review Gala, where Freeman was awarded the Best Actor Award for Driving Miss Daisy.

John Travolta let "Mikey" steal his shades.

John Travolta and Mikey from Look Who's Talking
INTERFOTO/Alamy Stock Photo

At a 1990 press conference in Germany for the international release of Look Who's TalkingJohn Travolta posed with a stand-in for his pint-sized costar. And for more stars who've just had kids of their own, here are 15 Celebrities Who've Had Babies During the Pandemic.

Melanie Griffith and Don Johnson were a power couple.

Melanie Griffith and Don Johnson
Barry King/Alamy Stock Photo

Melanie Griffith and Don Johnson were in the midst of their second try at matrimony when they attended a charity gala together in 1990.

Carol Channing and Lynn Redgrave put their heads together.

Carol Channing and Lynn Redgrave
Adam Scull/ /MediaPunch/Alamy Stock Photo

The late musical comedy actress and the late renowned dramatic actress may have been born to tackle much different roles, but they look like kindred spirits at a 1990 party.

Bridget Fonda and Eric Stoltz were Hollywood royalty.

Bridget Fonda and Eric Stoltz
Barry King/Alamy Stock Photo

The year she appeared in The Godfather Part III, Bridget Fonda also started dating Some Kind of Wonderful's Eric Stoltz. They went to the 1990 Goodfellas premiere arm-in-arm and stayed together for the next eight years. And for more Hollywood memories delivered right to your inbox, sign up for our daily newsletter.

Laura Dern showed off her show business family.

Laura Dern, Mary Lanier, and Diane Ladd
Barry King/Alamy Stock Photo

There are three generations of talent in this photo from the 1990 Wild at Heart premiere: the film's star, Laura Dern; her grandmother, actress Mary Lanier; and her mother, actress Diane Ladd.

Gloria and Emilio Estefan were painfully chic.

Gloria and Emilio Estefan
Barry King/Alamy Stock Photo

Gloria and Emilio Estefan have been married for 42. The two musical powerhouses met when Gloria started to sing in Emilio's band, 14 years before this photo was taken at a CBS event in 1990.

Warren Beatty, Charlie Korsmo, and Madonna took the red carpet together.

Warren Beatty, Charlie Korsmo, and Madonna
Mark Reinstein/Alamy Stock Photo

Costars and briefly romantic partners, Warren Beatty and Madonna both donned shades for the premiere of their iconic 1990 comic strip movie. That's their young castmate Charlie Korsmo holding Madge's hand.

Barry Manilow and Bette Midler had the same hairstylist.

Barry Manilow and Bette Midler
Barry King/Alamy Stock Photo

Blond waves were all the rage 30 years ago, as evidenced by this matchy-matchy meeting of Barry Manilow and Bette Midler. The two musicians also have worshipful fan bases in common.

Natalie Cole was timeless.

Natalie Cole
Barry King/Alamy Stock Photo

The '90s gave everyone who lived through them a lot to be embarrassed about—mainly the wardrobe. But singer Natalie Cole's ensemble for the Pacific Heights premiere is notable because of how dated it isn't.

Kate Capshaw and Steven Spielberg weren't letting go.

Kate Capshaw and Steven Spielberg
Barry King/Alamy Stock Photo

Kate Capshaw and Steven Spielberg famously met when she was cast in his 1984 movie Indiana Jones and the Temple of Doom. They would get married in 1991, the year after they walked the red carpet of the 1990 Presumed Innocent premiere together. The two are still married and have seven children all together.

Jack Nicholson was as cool as ever.

Jack Nicholson
Barry King/Alamy Stock Photo

There's no effortless cool like Jack Nicholson's, and this snap of him at a 1990 charity gala pretty much sums it up.

Sarah Jessica Parker and Robert Downey Jr. were young and in love.

Sarah Jessica Parker and Robert Downey Jr.
Barry King/Alamy Stock Photo

Long before they would be synonymous with their onscreen characters Carrie Bradshaw and Tony Stark, respectively, Sarah Jessica Parker and Robert Downey Jr. dated—for several years, in fact. This party pic was taken near the end of their romance—they would break up in 1991.

The Richie Family went full black tie.

Brenda Harvey Richie, Nicole Richie, and Lionel Richie
Barry King/Alamy Stock Photo

Yes, that's a tiny Nicole Richie dressed like a velvet cupcake (an iconic early '90s look). She was accompanying her dad, singer Lionel Richie, and mom, Brenda Harvey-Richie, to a charity bash.

Johnny Depp and Winona Ryder were the coolest pair.

Johnny Depp and Winona Ryder
Barry King/Alamy Stock Photo

Both idolized by their Gen X peers, Winona Ryder and Johnny Depp were like the prom king and queen of the early '90s—if the prom king and queen wore all black, that is. They only dated for four years, but remain close friends.

Kiefer Sutherland and Julia Roberts were an item.

Kiefer Sutherland and Julia Roberts
Barry King/Alamy Stock Photo

Kiefer Sutherland and Julia Roberts strutted down the red carpet for 1990's Flatliners together after they fell in love on set (while both in relationships with other people). Sadly, this work romance wasn't met to be either—they ended their engagement in 1991.

Sage Young
Sage Young is the Deputy Entertainment Editor at Best Life, expanding and honing our coverage in this vertical by managing a team of industry-obsessed writers. Read more
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