1. Early in career: Jennifer Lawrence.
Weinstein Co. / Courtesy Everett Collection
In 2013, she won Best Actress for playing Tiffany Maxwell in Silver Linings Playbook. Jennifer was only 22, making her the second-youngest person ever to win in that category.
2. Late in career: Michelle Yeoh.
Allyson Riggs / A24 / Courtesy Everett Collection
She made her acting debut back in 1984 and has been featured in over 60 TV or movie projects. Michelle finally won Best Actress last year at 60 years old for portraying Evelyn Wang in Everything Everywhere All at Once.
3. Early in career: Cuba Gooding Jr.
TriStar Pictures / Courtesy Everett Collection
Less than 10 years after his film debut, he won Best Supporting Actor in 1997 for his portrayal of Rod Tidwell in Jerry Maguire. Cuba was 29, becoming one of the few men to take home the award before the age of 30.
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4. Late in career: Leonardo DiCaprio.
20th Century Fox / Courtesy Everett Collection
Despite incredible performances all the way back to his Titanic days, the actor didn't snag an Oscar until 2015, when he won Best Actor for playing Hugh Glass in The Revenant.
5. Early in career: Lupita Nyong'o.
Fox Searchlight / Courtesy Everett Collection
In 2014, she won Best Supporting Actress for her performance as Patsey in 12 Years a Slave. This role was Lupita's feature-film debut.
6. Late in career: Kate Winslet.
Weinstein Co. / © Weinstein Co. / Courtesy Everett Collection
She received five previous Oscar nominations before finally winning in 2009. Kate took home the award for Best Actress for playing Hanna Schmitz in The Reader.
7. Early in career: Julie Andrews.
Courtesy Everett Collection
In 1965, Julie won Best Actress for starring in Mary Poppins. It was her debut film performance.
8. Late in career: Jeff Bridges.
Fox Searchlight / Courtesy Everett Collection
Jeff started acting back in the '50s. He was nominated for an Oscar five times before finally winning in 2010 for his performance as Otis "Bad" Blake in Crazy Heart.
9. Early in career: Angelina Jolie.
Columbia Pictures / Courtesy Everett Collection
In 2000, she won Best Supporting Actress for playing Lisa Rowe in Girl, Interrupted. Angelina was just 24 years old.
10. Late in career: Brendan Fraser.
A24 / Courtesy Everett Collection
Last year, he won Best Actor for his portrayal of Charlie in The Whale. It was a big comeback moment for Brendan, whose career began over 30 years ago.
11. Early in career: Hilary Swank.
Searchlight Pictures / Courtesy Everett Collection
In 2000, Hilary won Best Actress at age 25 for playing Brandon Teena in Boys Don't Cry. She also won Best Actress for her performance in Million Dollar Baby just five years later.
12. Late in career: Regina King.
Annapurna Pictures / Courtesy Everett Collection
Regina got her start as a teenager, playing Brenda Jenkins on 227 in the mid-'80s. She finally won Best Supporting Actress in 2019 for her performance as Sharon Rivers in If Beale Street Could Talk.
13. Early in career: Jodie Foster.
Courtesy Everett Collection
At 26, she won Best Actress in 1989 for playing Sarah Tobias in The Accused. Three years later, Jodie won again for her performance in The Silence of the Lambs.
14. Late in career: Sean Penn.
Warner Bros. / Courtesy Everett Collection
He began acting in 1974 but didn't snag an Oscar until 2003 — nearly 30 years later — for playing Jimmy Markum in Mystic River.
15. Early in career: Jennifer Hudson.
DreamWorks / Via youtube.com
In 2007, Jennifer won Best Supporting Actress for playing Effie White in Dreamgirls. She was just 25, and the role was her debut film performance.
16. Late in career: Ke Huy Quan.
A24 / Via youtube.com
In a beautiful comeback story last year, he won Best Supporting Actor for playing Waymond Wang in Everything Everywhere All at Once. Previously, the actor was best known for his roles in Indiana Jones and the Temple of Doom and The Goonies in the mid-'80s.
17. Early in career: Charlize Theron.
Newmarket Releasing / © Newmarket Releasing / Courtesy Everett Collection
Less than 10 years into her acting career, she won an Oscar at 28. Charlize took home the 2004 award for Best Actress for her portrayal of Aileen Wuornos in Monster.
18. And finally, late in career: Anthony Hopkins.
Orion Pictures Corp. / Courtesy Everett Collection / Everett Collection
Though he made his acting debut in 1965, Anthony didn't win an Oscar for nearly 30 years. It wasn't until 1992 that he took home Best Actor for his portrayal of Hannibal Lecter in The Silence of the Lambs. And it took nearly 30 more years for him to win again with his performance in The Father.