Jessica Chastain Recalls The Sweet Way Taylor Swift Helped Her Through A Breakup, And Why She Remembers It 'All Too Well'

From left to right: Jessica Chastain on The Tonight Show and Taylor Swift in the Long Pond Studio Sessions for Folklore.
(Image credit: NBC and Disney+)

Taylor Swift is the queen of breakup songs, and it turns out that she’s also the queen of helping others get through a breakup too. While her music has obviously helped Swifties get through their relationship struggles for years, the singer has personally curated playlists to help others get through these tough times too. And Jessica Chastain revealed she was a recipient of one while recalling a sweet story about the pop star that she remembers “All Too Well” (in a very good way). 

Chastain was chatting with Jimmy Fallon on the Tonight Show about seeing Swift’s Eras Tour in Mexico City – which is where the fun little change to “We Are Never Ever Getting Back Together” happened – earlier this year. However, that wasn’t the first time the Oscar winner had interacted with the pop star as she recalled the first time they met, and the sweet way the “All Too Well” singer helped her through break up:

I met Taylor. She’s actually really sweet. [She’s] the best, it’s crazy. I met her in 2011 at the Met Ball and we were both – it was the first year I was invited to the Met Ball, first year I had movies out. And we were both sitting next to each other, we were next to Ryan Murphy, who was just starting to become successful with all of his TV shows, and she was so sweet. I just went through a breakup but I was talking to her about that. And we went and danced together. It was such a fun night.

First of all, this night sounds epic. These two attended the Meg Gala long before Jessica Chastain became an Oscar winner and before many of the albums Swift is now releasing as re-recordings were dropped the first time. Continuing to tell this story about the "Cruel Summer" singer and her kind gesture that helped her get through a breakup, the Zero Dark Thirty star said: 

And then the next day, I had an email from iTunes that said ‘Taylor Swift,’ whatever, and I just thought it was a Taylor Swift album. She had made me a breakup playlist that she sent me. Isn’t that the sweetest thing?

While you’d expect this kind of gesture from a bestie (like I’m sure Swift and Blake Lively have done this for each other), it sounds like the "Love Story" singer made one for Chastain after only knowing her for one day. It turns out, the Molly’s Game star was also baffled in the best way by the playlist, as she said:

And here I thought it was a Taylor Swift advertisement. And it was like, ‘Wait a minute.’ And she curated all these breakup songs to send me to help me get through my breakup.

Swift could have easily included many of her own songs – like “All Too Well,” “You’re Losing Me” and “Forever & Always”...although most of those weren’t out in 2011. However, knowing the thought and detail she puts into her work, I imagine the playlist was thoughtfully considered and impeccably curated. 

Clearly, Jessica Chastain was very touched by this gesture as she giddily re-told the story 12 years after it happened. Based on her enthusiasm about Swift, and the sweet photo she shared of them at the Eras Tour (seen below), I’d imagine she would have done the same thing for the pop star when she and Joe Alwyn broke up earlier this year. 

However, now Chastain has been married since 2017, and Swift is in a relationship with Travis Kelce. Maybe now they can share playlists of love songs on Spotify?

Overall, this sweet interaction between Jessica Chastain and Taylor Swift continues to show how beloved the pop star is for both her music and her kind actions. From Mariska Hargitay naming her cat “Karma” after the singer’s song to Kevin Costner posting about his love of the Eras Tour, A-listers of all kinds have been sharing their adoration for the “Anti-Hero” singer, and for good reason. It’s because when someone shows you love or appreciation like Swift showed The Eyes of Tammy Faye actress, you remember it “All Too Well.” 

Riley Utley
Weekend Editor

Riley Utley is the Weekend Editor at CinemaBlend. She has written for national publications as well as daily and alt-weekly newspapers in Spokane, Washington, Syracuse, New York and Charleston, South Carolina. She graduated with her master’s degree in arts journalism and communications from the Newhouse School at Syracuse University. Since joining the CB team she has covered numerous TV shows and movies -- including her personal favorite shows Ted Lasso and The Marvelous Mrs. Maisel. She also has followed and consistently written about everything from Taylor Swift to Fire Country, and she's enjoyed every second of it.