A Cinderella Story and Freaky Friday were two of the biggest movies in the tween market during the 2000s. The former starred Hilary Duff and came out in 2004, and the latter starred Lindsay Lohan and premiered in 2003. These "it" girls were everywhere, and they both got to work with Chad Michael Murray on their respective films.

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Hilary and Lindsay had plenty of things in common during their feuding years, and a popular co-star was one of them. Which film is responsible for Chad Michael Murray's best movie role of the 2000s?

Freaky Friday: Hilarious Co-Stars

Jamie Lee Curtis clutches her face as Lindsay Lohan looks on in Freaky Friday.

In Freaky Friday, Chad Michael Murray works with both Jamie Lee Curtis and Lindsay Lohan. This dynamic duo is perfect for a film about a mom and a daughter, and Chad Michael Murray fits into their lives well as Jake. He doesn't have the biggest role in the film, but he deals with the confusion of crushing on a girl who is stuck in her mother's body--and he doesn't even know it! The ironic situation makes Freaky Friday one of the funniest programs on Disney+.

A Cinderella Story: Hilary Duff, Herself

A Cinderella Story

Hilary and Lindsay definitely knew Chad Michael Murray was filming with both of them, and some viewers would say that Murray shines the most in the spotlight with Hilary Duff. She was fresh from her Lizzie McGuire beginnings, and Murray had just begun his run on One Tree Hill. 

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By the time these predictable crushes finally get together, fans are sold on the fact that their characters, Austin Ames and Sam Montgomery, are meant to be.

Freaky Friday: Chemistry With Lindsay

Freaky Friday Chad Michael Murray and Lindsay Lohan

As Jake the heartthrob, Chad Michael Murray has phenomenal chemistry with Lindsay Lohan's Anna Coleman. The problem is, Jake doesn't know that Anna and her mom have switched bodies. He winds up hanging out with Tess Coleman (Jamie Lee Curtis), which makes sense seeing that Tess is really Anna. It's fun to watch this mix-up play out in the movie, and Chad and Lindsay get their moment at the end of it all. Some would say that they are the best teen movie couple of their genre.

A Cinderella Story: Amazing Soundtrack

A Cinderella Story Dance

The soundtrack to A Cinderella Story was one of the best motion picture soundtracks of any 2000s tween film. Half of it was basically another Hilary Duff CD, including tunes like "Anywhere but Here," "Crash World," and the Hilary and Haylie Duff duet "Our Lips Are Sealed." The rest of the album had top-notch Jesse McCartney favorites as well as Edwin McCain's soaring "I'll Be." Chad Michael Murray simply gets to dance among the greatness.

Freaky Friday: Special Connection To The Music

In Freaky Friday, Chad Michael Murray has a much deeper connection to the music as Jake. He is attracted to Anna, in part, because of their shared artistic interests. Those interests are still Anna's after the body switch, but she expresses them within her mom's body. After the switch, Tess shows up with a new look to reflect her inner daughter's taste. The mom shares coffee with Jake, and the two have a moment over a cover of "Baby One More Time."

A Cinderella Story: Fairytale Romance

A Cinderella Story Hilary Duff as Sam and Chad Michael Murray as Austin

Austin Ames and Sam Montgomery have the 2004 version of a fairytale love story, hence the movie's title. Technology was still on the rise at that point in the decade, so Sam and Austin's talks consist of simple texts, Instant Messages, and emails. Like the real Cinderella, things don't work out for Sam and her prince until the end of the tale.

Freaky Friday: Face To Face Romance

Chad Michael Murray and Lindsay Lohan in Freaky Friday

As mysterious and warm as Sam and Austin's story is, it's nice to see Chad Michael Murray interact with his love interest throughout the entirety of Freaky Friday. Even though he doesn't understand who he's actually talking to most of the time, Jake gets to know Tess/Anna face to face. The awkward feelings he develops for someone twice his age (physically, anyway) are still sweet and kind of cute.

A Cinderella Story: Stereotypical Football Player Redemption

A Cinderella Story Hilary Duff as Sam and Chad Michael Murray as Austin

Austin isn't exactly the definition of a knight in shining armor. The football player falls into all the stereotypes of popularity, conceitedness, and self-obsession. Thankfully, he's a different person inside with much more depth and purpose (High School Musical, anyone?). Austin's redemption is a little far-fetched, but it sold a lot of tickets and seemed right for a movie starring Disney Channel's biggest celebrity.

Freaky Friday: No Dating The Mean Girl

Julie Gonzalo Freaky Friday and A Cinderella Story

Besides featuring Chad Michael Murray, Freaky Friday and A Cinderella Story have another comical similarity. In both films, Julie Gonzalo plays the mean girl. She is Stacey Hinkhouse in Freaky Friday, and she's Shelby in A Cinderella Story.

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Austin Ames is caught up in Shelby's crowd throughout A Cinderella Story and has trouble breaking up with the terrible cheerleader. One great quality of Freaky Friday is that the leading man is not obsessed with the mean girl.

A Cinderella Story: "Waiting For Rain In This Drought"

A Cinderella Story Rain

Though he doesn't say it, himself, Austin Ames is associated with Sam's most iconic line in A Cinderella Story: "Waiting for you is like waiting for rain in this drought. Useless and disappointing." Those oft-quoted words are juxtaposed immediately with rainfall and a long kiss, right in the football bleachers. Chad Michael Murray will always be able to say he was a part of that.

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