Hilary Swank won Best Actress at just 25 years old forBoys Don’t Cry.

1.Early in career: Jennifer Lawrence.

2.Late in career: Michelle Yeoh.

Jennifer in a black coat and scarf looking away from the camera

3.Early in career: Cuba Gooding Jr.

4.Late in career: Leonardo DiCaprio.

5.Early in career: Lupita Nyong’o.

6.Late in career: Kate Winslet.

Michelle with eyeball on the forehead, wearing a quilted jacket and floral shirt, gazing to the side

7.Early in career: Julie Andrews.

8.Late in career: Jeff Bridges.

9.Early in career: Angelina Jolie.

Cuba with a bald head and an earring, wearing a leather jacket

10.Late in career: Brendan Fraser.

11.Early in career: Hilary Swank.

12.Late in career: Regina King.

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13.Early in career: Jodie Foster.

14.Late in career: Sean Penn.

15.Early in career: Jennifer Hudson.

Leonardo DiCaprio as Hugh Glass, in fur attire, gripping a rifle in a snowy terrain from the movie "The Revenant"

16.Late in career: Ke Huy Quan.

17.Early in career: Charlize Theron.

18.And finally, late in career: Anthony Hopkins.

Lupita sitting on grass, leaning on a tree, wearing a long, patterned dress in scene from 12 Years a Slave

Kate Winslet rests on her forearms in bed, looking pensive, with a person reading beside her

Julie as Mary Poppins, wearing a hat with flowers and fruit, a bow tie, and a jacket

Jeff with a beard playing an acoustic guitar, focused on the strings, wearing a denim shirt

Angelina in a yellow T-shirt sitting, looking at the camera with a slight smile, in Girl, Interrupted

Brendan looking away from the camera in a kitchen setting in a scene from The Whale

Hilary Swank portraying Brandon Teena in a plaid shirt, seated with hands clasped and looking thoughtful

Regina in a striped jacket looking back over her shoulder indoors

Jodie Foster in a scene from the movie "The Accused," wearing a jacket and looking pensive

Sean sitting in a store with shelves full of products in the background

Jennifer in Dreamgirls, singing

Quan in a a striped shirt with surprised expression in a mall-like setting

Charlize looking intense in a scene from Monster

Anthony wearing a T-shirt as Hannibal Lecter