Hilary Swank: Teen Drama's Oscar Winner

Picture this: You’re signed to a season-long deal as a series regular on “Beverly Hills, 90210,” but you’re fired partway through the season and only appear in 16 episodes.

Your career’s over, right?

Not if you’re Hilary Swank.

No, if you’re Hilary Swank, you go from being fired from “Beverly Hills, 90210” in 1998 to winning an Oscar in 2000.

And that was no fluke. Swank didn’t go on to win just one Oscar. She went on to win two, with the second coming just five years later.

What’s more, Swank is the only series regular from one of the core six teen dramas to have an Academy Award (much less two) to her name. Michelle Williams of “Dawson’s Creek” has been nominated five times but has yet to win — always the bridesmaid, never the bride. Given how revered Williams is for her acting, it’s all the more incredible that Swank has gone two for two.

So, what were the films and roles that earned Swank Oscar glory twice over?

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Best Actress for Boys Don’t Cry (2000)

To bring the real-life story of Brandon Teena, a trans man who was murdered in a brutal hate crime, to the big screen, Swank cut off the shoulder-length locks she had as Carly Reynolds and transformed her physical appearance. While it’s unlikely the cis Swank would be cast in the role today, her performance was met with critical acclaim at the time and catapulted her into the spotlight that never shone on her during her brief stint on “Beverly Hills, 90210.” In addition to the Oscar, Swank won a Golden Globe, Critics’ Choice, and Independent Spirit award for the project.

Best Actress for Million Dollar Baby (2005)

If Swank’s performance in Boys Don’t Cry could be called understated, her portrayal of boxer Margaret “Maggie” Fitzgerald in Million Dollar Baby is arguably the opposite. Here, her slight frame is muscular, her hair often pulled back into a ponytail or braid. Unlike in Boys Don’t Cry, Swank isn’t the one getting beat — she’s the one doing the beating. That is, until a match goes horribly, irrevocably awry. Despite the role being vastly different from her first Oscar-winning part (though no less tragic), Swank again won over the industry. Besides the Academy Award, she took home the Golden Globe and the SAG award, while the film itself won the Best Picture Oscar (among many other accolades).

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Not surprisingly, Swank’s pivot from being fired from “Beverly Hills, 90210” to reaching the pinnacle of Hollywood occasionally comes up in interviews.

She told The Sydney Morning Herald in 2007:

“They sacked me because I wasn’t a good enough actress. I was devastated. I thought, if I’m not good enough for 90210, I’m not good enough for anything. I’ll never make it.”

In 2018, she recalled to the Los Angeles Times:

“They were like, ‘Look, it’s not working.’ And I couldn’t move. I was like, ‘What’s not working? Me? Am I bad? I’m not working because I’m bad?’”

And in 2020, Swank said in a People interview:

“I was fired from ‘Beverly Hills, 90210.’ That shaped me into the person who can say, ‘Oh, that didn’t work out, I really wanted it to; I worked really hard to make it happen. I pulled out all the stops. I upturned every rock. I pushed as far as I could, and if it didn’t happen, I’m going to trust there’s a reason why it didn’t’ … I’m so grateful though — it’s why I’m where I am today.”

That Los Angeles Times article went on to describe Swank as “‘90210’s most decorated veteran” — which she remains today.

Swank may have seemed like a laughing stock back in 1998 but there’s no arguing she got the last laugh.