Hollywood Glow-Ups: 25 Stars at Their First Oscars vs. Now

Anne dazzled in 2007 at her first Oscars thanks to The Devil Wears Prada fame. Fast forward twenty years, she’s still owning the carpet and even got to team up with the legendary Anna Wintour. When Anne asked about her black floral gown, Anna just teased, “And the nominees are…” Classic!

Demi’s first Oscars in '89 had her looking just as stunning as the star she is today. She was rocking it with Bruce Willis back then, and now she’s still lighting up stages and even joined in on heartfelt tributes. Timeless, right?

Adrien snagged his Best Actor Oscar in 2003 for The Pianist and stole the show with a totally unexpected kiss on Halle Berry. Fast forward two decades, Halle kissed him right back at the red carpet! Now that’s Oscars romance. This year, Adrien kept it cool presenting Best Actor and poked fun at his super long acceptance speech.

Ed first showed up with his wife Amy in 1986. She didn’t win that year, but this Oscars couple is still going strong. Ed’s bagged a few nominations himself, but he’s all about cheering on Amy, who finally snagged her golden statue recently. Teamwork makes the dream work!

Kate stepped onto the Oscars scene at 21, rocking an outfit and hairdo straight out of the early 2000s. Nominated for Almost Famous, she kept fans hooked with her charm ever since. This year she went for a more grown-up role and look, showing just how far she’s come.

Michael’s first Oscars was in 2014, supporting Fruitvale Station. No noms yet, but everyone noticed him. Fast-forward to 2026, and he’s got a shiny Best Actor Oscar for playing twins in Sinners. Talk about leveling up!

Nicole’s first Oscars was all about supporting her then-husband Tom Cruise. Since then, she’s wowed in everything from Moulin Rouge! to Being the Ricardos. This year, she flirted a little on stage with co-star Ewan McGregor and reminded us why she’s Hollywood royalty.

Timothée rocked his first nod at 22 with Call Me by Your Name and instantly became everyone’s fave. Since then, he’s racked up noms for A Complete Unknown and Marty Supreme. Even when he doesn’t win, the guy’s got style for days.

Leo’s first Oscars was way back in 1994, nominated for What's Eating Gilbert Grape. After a few close calls, he finally snagged his Oscar for The Revenant in 2016. This year, he was nominated again but watched Michael B. Jordan steal the spotlight. Still, Leo’s total win streak is impressive.

Back in 2000, Ethan showed up at the Oscars with Uma Thurman, presenting an award. Over the years, he’s nabbed five noms, including one this year for Blue Moon. Still as cool as ever!

Gwyneth’s been a regular on the Oscars scene since ’94 when she was just 21. She took home an Oscar for Shakespeare in Love and is back with a fresh nom this year for Marty Supreme. Plus, she announced a new award for Best Casting. Talk about multitasking!

In ’08, Heidi made a splash in a fiery red Galliano gown. Years later, she’s still taking fashion risks and wowed in a sheer dress with pearl choker at the latest ceremony. If you’re gonna do fashion, might as well do it big.

Barbra’s Oscars history spans decades. She first presented in 1968, won Best Actress the next year, and recently stole the show with a soulful performance. Seven decades of star power? Yes, please!

Rachel once presented an award shortly after hitting it big in Mean Girls and The Notebook. Later, she scored an Oscar nom for Spotlight and recently honored other stars in the “In Memoriam” segment. Always classy, always present.

Billy started by presenting Best Sound in 1988 and went on to host the Oscars nine times. His quick wit has earned him Emmys and our hearts. Recently, he gave a touching tribute to director Rob Reiner. The King of Oscars hosting, for sure.

Emma’s first Oscars was as part of The Help cast in 2012. Since then, she’s racked up six nominations and two Best Actress wins - La La Land and Poor Things. This girl’s got charm and talent to spare.

Pedro’s first Oscars was just last year, and he surprised fans with a fresh, clean-shaven look. This year, he presented two awards alongside Sigourney Weaver. Not bad for a relative newbie, huh?

Back in 2013, Channing danced with Charlize Theron during the Oscars opening. This year, he presented a couple of awards and had a hilarious moment when Robert Downey Jr. joked about his Magic Mike thong. Classic Channing: cool, funny, and a little cheeky.

Kathy won the Best Actress Oscar in 1991 for Misery, playing a seriously intense role. This year, she was part of a touching tribute to filmmaker Rob Reiner and his wife. She always brings sincerity and class to the stage.

Steven made his Oscars debut in 1976 with Jaws, a film that snagged almost all its noms. He’s won three Oscars and recently showed up supporting the movie Hamnet. Spielberg’s Oscars story is pure Hollywood legend stuff.

Ava came on the Oscars scene in 2014 with Selma, a powerful movie about Martin Luther King Jr. This year, she stepped out hand-in-hand with her boyfriend and proudly talked about rocking the Oscars with her honey. Now that’s an entrance!

Goldie won Best Actress for Cactus Flower but didn’t even know it - talk about a wild story! She missed the ceremony but made up for it by attending this year with her daughter Kate Hudson, who’s now best Oscar friend and nominee. Family goals alert!

Kirsten presented Best Film Editing in 2005, rocking a super 2000s vibe. Recently, she returned to support her husband Jesse Plemons, showing that supporting your own is the new black.

Alicia walked the carpet young and fresh in ’96 before presenting Best Makeup. Famous for Clueless, she’s still in the movie game acting alongside big names in Bugonia. Forever young, forever iconic.

Spike Lee’s first Oscars nod was for Do the Right Thing, and even back then, stars called out the Academy for missing the big picture. Fast-forward, Spike’s still here supporting friends, always speaking truth to power. Respect!