Taylor Swift Cast Dylan O’Brien in ‘All Too Well’ Because of His ‘Dangerous Charm’

Grammy-winner Taylor Swift delighted fans when she released All Too Well: The Short Film to accompany “All Too Well (10 Minute Version) (Taylor’s Version) (From the Vault)”. The film, starring Sadie Sink and Dylan O’Brien has since amassed over 76 million views on YouTube. 

All Too Well: The Short Film tells the story of an ill-fated romance widely-speculated to be based on Swift’s real-life relationship with actor Jake Gyllenhaal. And during a panel at the 2022 Toronto International Film Festival, she revealed exactly why she handpicked O’Brien to play the leading man — whose character is a not-so-subtle jab at her famous ex.

Who is Dylan O’Brien?

dylan o'brien
Dylan O’Brien attends the “Not Okay” New York Premiere at Angelika Film Center on July 28, 2022 in New York City. | Dia Dipasupil/Getty Images

O’Brien’s big break came at the age of 18, when he auditioned for MTV’s hit show Teen Wolf. Based on the 1985 movie of the same name, the series ran for six seasons between 2011 and 2017. In the show, O’Brien played Stiles Stilinski, the goofy best friend to high-school-student-gone-werewolf, Scott McCall (Tyler Posey). 

The actor later made his first leap into feature-length films with the independent comedy High Road, and later co-starred in the comedy The Internship. He also starred in the film adaptation of the best-selling Maze Runner series as protagonist Thomas in all three films.

More recently, O’Brien appeared in Quinn Shepard’s Not Okay. In the film, he played the character of Colin, a self-absorbed influencer and the love interest of Danni (Zoey Deutch). He’s also set to star in the upcoming comedy Maximum Truth and the mystery-thriller, The Vanishings at Caddo Lake.

Taylor Swift said Dylan O’Brien has ‘this dangerous charm’

According to Swift, it was crucial to the heart of All Too Well: The Short Film to cast both Sink and O’Brien in the leading roles. “It was what my heart needed for this film,” said Swift during her interview at TIFF. “It was a very instinctual decision based on having watched their performances.”

Swift added that she had never seen the two actors play characters like the ones in All Too Well. And wanted to give them a unique opportunity. She specifically wondered if Sink, who most television viewers recognize from Netflix’s Stranger Things, would even want to play a romantic lead — a significant departure from her previous roles.

But when it came to casting O’Brien, Swift had a different line of thinking. “With Dylan, it was that charisma,” the Blank Space singer said. “I’d seen his films and I’d seen him…I mean, even just him doing an interview, you can see that he’s got this dangerous charm.”

The character O’Brien plays in All Too Well: The Short Film is far from likable, but has a unique draw. So Swift thought he was the perfect actor for the part.

“Him as a person, he’s not a dangerous…but he’s dangerously charming,” she quipped. “That is a power that he has.”

How Taylor Swift’s ‘All Too Well’ short film came to be

All Too Well: The Short Film was released simultaneously with Swift’s Red (Taylor’s Version) re-release. The album is part of her ongoing efforts to re-record all of her music.

The song itself — “All Too Well” — was a fan-favorite from the original album. But the new 10-minute version quickly became a chart-topping hit. As shared by Billboard, Red (Taylor’s Version) launched at No. 1 on the Billboard 200, and scored the biggest sales week for an album in 2021 with the equivalent of 369,000 sales. “All Too Well” premiered at No. 1 on the Billboard Hot 100 and earned a combined 54.4 million U.S. streams in the first week alone.

Swift hosted a small premiere event for All Too Well: The Short Film in New York City where she also gave a live performance of the song. Upon its release, the film was widely praised by both fans and critics, leading many to hope that Swift will continue her directorial career in the future.

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