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Throughout the course of her career, Jennifer Coolidge has played many iconic characters. Before she was receiving praise and acclaim for her portrayal of Tanya McQuoid in The White Lotus, she gave standout performances in films like Legally Blonde as Paulette Bonafonté. And Hilary Duff fans will undoubtedly remember Coolidge as the wicked stepmother, Fiona.

Jennifer Coolidge, Hilary Duff, and Chad Michael Murray on the red carpet
Jennifer Coolidge, Hilary Duff, and Chad Michael Murray | Cohen/WireImage

Hilary Duff and Jennifer Coolidge were both cast in ‘A Cinderella Story’

Back in 2004, Duff and Coolidge starred opposite each other in A Cinderella Story. Coolidge played the evil stepmother of Duff’s character, Sam Montogomery. Throughout the course of the film, Fiona treats Sam terribly, forcing her to work overtime and verbally belittling her. Fans of the film will surely recall Fiona telling Sam “You’re not very pretty and you’re not very bright.”

One of Duff’s kids recreated her favorite moment with Coolidge

But while their characters certainly butted heads, when the cameras weren’t rolling, Coolidge and Duff got along great. While on Watch What Happens Live with Andy Cohen, Duff was quick to sing her former castmate’s praises. “I can’t even begin to tell you how much I’ve just been, like, obsessed with this past year for Jennifer Coolidge,” Duff gushed. “It’s been really cool to see.”

While on the talk show, Duff also shared her favorite memory of Coolidge. “My favorite moment was her rubbing salmon on her face while filming A Cinderella Story and talking about the omegas,” Duff recalled. Turns out Duff’s son, Luca, the eldest of her three kids, inadvertently recreated this moment when he was just a toddler. “My son actually started eating sushi when he was like three and had a similar moment, and I looked and I was like you’re just rubbing raw salmon on your face,” Duff recalled. “And it’s, like, soft and he liked it and it reminded me of her. And she’s just everything.”

The singer gushed about her former castmate’s long career

It’s pretty hilarious that Duff’s son gave her a callback to a beloved memory with Coolidge. The How I Met Your Father star also raved about how excited she was to see Coolidge getting her flowers in recent years. “She’s always been a lovely human being, but I’m really proud to see her moment,” Duff shared about the Best in Show alum. “And I think it just reminds me that, being in this industry, I feel so lucky that anything can happen at any stage. It’s so dope.” 

Interestingly enough, Coolidge was having a bit of a self-proclaimed dry spell in her career several years back. Despite her talent and lengthy resume, she just wasn’t getting opportunities that she was excited about. However, after Ariana Grande publicly imitated the actor and put Coolidge in her “thank u, next” music video, Coolidge began to receive more attention and work. And, thanks to her iconic performances in both seasons of The White Lotus, the actor is more relevant and recognized than ever.