Many of Hollywood’s biggest stars have been in the spotlight so long, it’s easy to forget how they got there.
Some achieved their dream of winning an Oscar after years of hard work and daring roles, while others are still hoping to hear their names called.
The celebrities on this list have changed hairstyles, film genres, and even romantic partners over the years, but they have kept their love for their craft intact.
Here’s what many Hollywood icons looked like at their first Academy Awards, as young, starry-eyed entertainers starting their careers, compared to their latest appearances at the 2026 awards.
#1 Demi Moore—1989
Demi appears to have taken The Substance, as she still looks as stunning as she did in her first Oscars, when she attended with then-husband, Bruce Willis.
The actress, who was nominated last year, presented Best Cinematography at the Sunday ceremony and joined Billy Crystal’s Rob Reiner tribute.
Image source: Jim Smeal/Ron Galella Collection/Getty Images, Gilbert Flores/Penske Media/Getty Images
#2 Anne Hathaway—2007
Anne looked radiant when she attended her first Oscars in 2007. She was part of the cast of The Devil Wears Prada, which earned Meryl Streep a nomination for Best Actress.
Two decades later, the actresses reprised their roles in the sequel, set to hit theaters on May 1.
While Meryl did not attend the awards this year, Anne presented Best Costume Design with Dame Anna Wintour, widely believed to have inspired Meryl’s character, Miranda Priestly.
When Anne asked Anna what she thought about her black floral gown, the former Vogue editor responded, “And the nominees are…”
Image source: Frazer Harrison/Getty Images, Gilbert Flores/Penske Media/Getty Images
#3 Adrien Brody—2003
The New York-born actor took home his first Academy Award for Best Actor for The Pianist in 2003.
While receiving his Oscar, he passionately kissed the presenter, Halle Berry–a moment that became one of the most talked-about scandals in awards-show history.
On the Oscars red carpet last year, Halle ran over and passionately kissed Adrien, two decades after their memorable moment.
“I mean, how can you deny a man a kiss with Halle Berry?” Adrien’s partner, Georgina Chapman, told Extra on the red carpet. “He was more than fine,” she insisted.
The Brutalist star presented the Best Actor award this year and poked fun at himself for giving one of the longest Oscars speeches of all time.
Image source: J. Vespa/Getty Images, JC Olivera/WWD/Getty Images
#4 Nicole Kidman—1991
Nicole attended her first Oscars in 1991 to support her then-husband, Tom Cruise, who presented an award at the ceremony.
The actors had met two years earlier while working together in Days of Thunder.
The age-defying beauty has come a long way since then, starring in films like Eyes Wide Shut, Moulin Rouge!, The Hours, and Being the Ricardos.
This year, she presented the Best Picture award and had a flirtatious reunion with Moulin Rouge! co-star Ewan McGregor.
Image source: Ron Galella/Ron Galella Collection via Getty Images, Christina House/Getty Images
#5 Leonardo DiCaprio–1994
Leo attended his first Academy Awards in 1994. He was nominated for Best Supporting Actor for his role in What’s Eating Gilbert Grape, but lost to Tommy Lee Jones for The Fugitive.
This year, the Hollywood star was nominated in the Best Actor category for his role in One Battle After Another, but lost to Sinners’ Michael B. Jordan.
Leo was nominated a total of four times before finally winning his first Oscar in 2016 for The Revenant.
Image source: Barry King/Getty Images, Kevin Mazur/Getty Images
#6 Michael B. Jordan—2014
The actor hasn’t changed much since he first stepped onto the Oscars red carpet in 2014, when he attended the ceremony to support Fruitvale Station, directed by Ryan Coogler.
While the film wasn’t Oscar-nominated, it had received major recognition during that year’s awards season, including at Sundance and Cannes film festivals.
Fast-forward to 2026, when Michael took home the Best Actor award for his role as twins Stack and Smoke in Sinners. It was both his first Oscar nomination and his first win.
Image source: Jeff Vespa/Getty Images, Mike Coppola/Getty Images
#7 Timothée Chalamet—2018
The 30-year-old star first attended the prestigious awards show in 2018 when he was nominated for Best Actor for his performance in Call Me by Your Name.
At 22, he became one of the youngest nominees in the category in decades.
Timothée was later nominated for A Complete Unknown and, most recently, for Marty Supreme—for an award that ultimately went to Michael B. Jordan.
Image source: Dan MacMedan/Getty Images, Kevin Mazur/Getty Images
#8 Heidi Klum—2008
Back in 2008, the German model attended the 80th Academy Awards at the Kodak (now Dolby) Theater in a striking red gown by Galliano.
Heidi never lost her interest in taking fashion risks. For the Sunday ceremony, she hit the red carpet in a strapless sheer beige gown by Chrome Hearts which she accessorized with a pearl choker necklace.
Image source: Jeff Kravitz/FilmMagic, Mike Coppola/Getty Images
#9 Kate Hudson—2001
At just 21 years old, Kate was nominated for Best Supporting Actress for her role as Penny Lane in Almost Famous.
For the 2001 ceremony, she chose an outfit and hairstyle that screamed “early 2000s.”
Kate lost to Marcia Gay Harden that year for her performance in Pollock.
Her second nomination came this year, this time for Best Actress for Song Sung Blue. The award went to Hamnet’s Jessie Buckley.
Image source: Kevin Winter/Getty Images, Kevin Mazur/Getty Images
#10 Gwyneth Paltrow—1994
Gwyneth has been a regular on the Oscars red carpet ever since her first appearance in 1994, when she was a 21-year-old rising actress in Hollywood.
She would have to wait five years to win her first—and so far only—Oscar for her role in Shakespeare in Love.
At this year’s show, the Goop founder was nominated for Best Actress for Marty Supreme.
She also presented the new award for Best Casting, which went to One Battle After Another.
Image source: Ron Galella, Ltd./Ron Galella Collection via Getty Images, Arturo Holmes/Getty Images
#11 Barbra Streisand—1968
With a career spanning seven decades, Barbra has attended the Academy Awards ten times.
Her first Oscars were in 1968 when she presented the award for Best Original Song. The following year, she won Best Actress for Funny Girl at the age of 26, famously tying with Katharine Hepburn.
Last Sunday, the talented star presented the Robert Redford tribute, during which she performed The Way We Were.
Image source: Fotos International/Getty Images, Rich Polk/Penske Media/Getty Images
#12 Ed Harris—1986
Ed first attended the Oscars in 1986 with his wife, Amy Madigan. Madigan was nominated that year for Twice in a Lifetime, but lost to Anjelica Huston for Prizzi’s Honor.
Four decades later, the couple is still going strong. Ed beamed with pride as his wife finally took home the golden statuette for her performance in Weapons.
As for Ed, he has yet to win the prize, having been nominated a total of four times.
Image source: Ron Galella, Ltd./Ron Galella Collection/Getty Image, Michael Buckner/Penske Media/Getty Images
#13 Pedro Pascal—2023
Pedro surprised fans with his clean-shaven look at this year’s Oscars. The Chilean actor presented Best Production Design and Best Visual Effects with Sigourney Weaver.
His first Oscars appearance didn’t come that long ago. In 2023, the Last of Us star, who was enjoying a major surge in his popularity, presented two awards with Elizabeth Olsen.
Image source: Arturo Holmes/Getty Images , Myung J. Chun/Getty Images
#14 Channing Tatum—2013
At the 2013 Oscars, Channing danced to The Way You Look Tonight with Charlize Theron during the opening segment.
In addition to presenting two awards this year, the 21 Jump Street actor took part in another segment with Robert Downey Jr. and Chris Evans.
“I got you the official Channing Tatum thong from Magic Mike. Sequined, it’s got like a mirrorball effect. Light usage,” Robert joked,
“I have no words,” Chris replied.
Channing shouted from the audience, “Hey, I’m gonna need that back, though!”
Incredulous, the Iron Man star questioned, “For what?”
Image source: Jason Merritt/Getty Images, Frazer Harrison/Getty Images
#15 Emma Stone—2012
In 2012, Emma attended the Oscars as part of the cast of The Help, which was nominated for Best Picture that year.
The actress has since been nominated a remarkable six times, most recently this year for Bugonia.
She has received two Best Actress awards, the first for La La Land and the second for Poor Things.
Image source: Donato Sardella/WWD/Penske Media/Getty Images, Julian Hamilton/Getty Images
#16 Ethan Hawke—2000
Ethan posed with his then-wife, Uma Thurman, at the 72nd Academy Awards in the year 2000.
The couple, who share two children, presented together the award for Best Documentary Feature.
The 55-year-old actor has been nominated for five Oscars, including this year for his work in Blue Moon.
Image source: KMazur/Getty Images, Arturo Holmes/Getty Images
#17 Rachel McAdams—2006
The Canadian actress presented the award for Best Technical Achievement at the 2006 Oscars, two years after she portrayed Regina George in Mean Girls and Allie in The Notebook.
In 2015, Rachel received an Oscar nomination for her role in Spotlight.
This year, she was part of the “In Memoriam” segment, presenting the Diane Keaton and Catherine O’Hara tribute.
Image source: Eric Neitzel/Getty Images, Rich Polk/Penske Media/Getty Images
#18 Billy Crystal—1988
In the late 1980s, Billy presented the Best Sound award at the 60th Oscars.
The actor and comedian went on to host the glitzy ceremony a total of nine times. His witty and warm hosting style even earned him two Emmys.
At this year’s Oscars, Billy paid a touching tribute to Rob and Michele Reiner. He and Rob worked together on When Harry Met Sally…, which Rob directed and Billy starred in.
They also collaborated on The Princess Bride, directed by Rob, in which Billy played Miracle Max.
Image source: Ron Galella, Ltd./Ron Galella Collection/Getty Images, Rich Polk/Penske Media/Getty Images
#19 Kirsten Dunst—2005
Kirsten joined Orlando Bloom in 2005 to present Best Film Editing. She styled her hair in an updo and donned a very 2000s pink dress.
The Power of the Dog actress returned to the ceremony last Sunday to support her husband, Jesse Plemons, who starred in Bugonia.
Image source: SGranitz/Getty Images, Mike Coppola/Getty Images
#20 Goldie Hawn—1971
In 1971, Goldie presented the award for Best Actor at the 43rd Academy Awards.
The previous year, she had won Best Actress for Cactus Flower, but did not attend the ceremony.
“I never got dressed up. I never got to pick up the award. I regret it,” she told Variety in 2023, explaining that she didn’t expect to win at all.
“I forgot it was on television that night,” Goldie admitted. “Then I woke up to a phone call at like 4 in the morning. And it was a man’s voice and he said, ‘Hey, congratulations, you got it.’ ‘I got what?’”
This year, the star attended the ceremony with her daughter and Best Actress nominee, Kate Hudson.
Image source: Ron Galella/Ron Galella Collection via Getty Images, Kevin Mazur/Getty Images
#21 Ava DuVernay—2014
In 2014, the director released one of the most successful films of her career: Selma, a biopic about Martin Luther King Jr. The film was nominated the following year for Best Picture but lost to Birdman.
Glory, the song by John Legend and Common for Selma, won for Best Original Song.
At the March 15 ceremony, the filmmaker went public with her boyfriend.
When asked by Essence to fill in the blank in response to “I am proud of myself for…,” Ava beamed as she replied, “Right now I am proud of myself for coming to the Oscars with my honey.”
Image source: Axel Koester/Corbis via Getty Images, Kevin Mazur/Getty Images
#22 Steven Spielberg—1976
A veteran of the Oscars, Steven first attended the awards show in 1976. His film Jaws won all its nominations except Best Picture.
The three-time Oscar winner was present at the ceremony this year in support of Hamnet, which he produced.
Image source: Michael Ochs Archives/Getty Images, John Shearer/Getty Images
#23 Alicia Silverstone—1996
Back in 1996, a 19-year-old Alicia Silverstone walked the Oscars red carpet before presenting the award for Best Makeup.
The previous year, the “it girl” had her big break in the teen comedy Clueless.
Alicia, now 49, portrayed Sandy Gatz, Teddy’s mother, in Bugonia.
Image source: Vinnie Zuffante/Getty Images, Jeff Kravitz/Getty Images
#24 Kathy Bates—1991
In 1991, Kathy won the Best Actress award for her performance in Misery, where she played the obsessive fan Annie Wilkes. It was her first nomination and, so far, only win.
Her appearance on stage this year was far more somber, as she joined the tribute for late filmmaker Rob Reiner and his wife, Michele.
Image source: Vinnie Zuffante/Getty Images, Mike Coppola/Getty Images
#25 Spike Lee—1990
The famous director first attended Hollywood’s biggest night in 1990. He was nominated in the Best Original Screenplay category for Do the Right Thing, but lost to Dead Poets Society.
At the ceremony, actress Kim Basinger called out the Academy for failing to nominate Spike’s film for Best Picture.
“We’ve got five great films here, and they’re great for one reason: They tell the truth,” she said. “But there is one film missing from this list that deserves to be on it because, ironically, it might tell the biggest truth of all. And that’s Do the Right Thing.”
The BlacKkKlansman filmmaker attended the ceremony this year to support actor and frequent collaborator Delroy Lindo, who was nominated for Sinners.
Image source: Ron Galella, Ltd./Ron Galella Collection/Getty Images, Gilbert Flores/Penske Media/Getty Images
