Unveiling the Untold Tale of Craig Gillespie: Unlikely Heroes and their Unlikely Chronicler

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September 27, 2023 at 6:00 a.m. EDT

Craig Gillespie

Philip Cheung for The Washington Post

Grooming by Sussy Campos

Styling by Rhonda Spies

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Craig Gillespie’s unique storytelling style, which often revolves around unconventional protagonists, derives from his own personal journey to Hollywood. The Australian-American film, television, and music video director, known for his work on “Dumb Money,” believes that his experiences in Australian surf, a tiny Manhattan apartment, and various commercial sets have shaped his ability to portray outsiders.

Gillespie, an identical twin from Sydney, admits to being more unruly and less focused compared to his academically inclined brother. He dropped out of the University of Sydney after just one semester, preferring to spend his time riding waves at the beach instead of attending classes. When he unexpectedly received a scholarship to the School of Visual Arts in New York, Gillespie made the 10,000-mile journey, settling into a cramped YMCA apartment. Over the course of a year, he transitioned from studying illustration to graphic design and then advertising.

Gillespie didn’t venture into show business until his early 20s, when he worked as an art director on commercial shoots. It was during this time that he discovered a passion for filmmaking. Reflecting on his teenage years, Gillespie remarks, “I was not somebody in my teen years that was running around with a camera thinking, ‘I’m going to be a director.’ But there seems to be an underlying theme in my work, dealing with outsiders – people who feel marginalized or like underdogs.”

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Gillespie, now 56 years old, has carved out a niche for himself by focusing on unlikely heroes. His breakout film, “Lars and the Real Girl” (2007), featured Ryan Gosling as a man in a relationship with a sex doll. Ten years later, Gillespie took on the controversial figure skater Tonya Harding in the critically acclaimed “I, Tonya.” Most recently, he delved into the backstory of the infamous Disney villain Cruella de Vil in the stylish “Cruella” (2021).

Rebecca Angelo, co-writer of “Dumb Money,” describes Gillespie as someone who approaches filmmaking with empathy. She notes that his own self-made path and drive allow him to connect deeply with the characters he portrays on-screen.

In “Dumb Money,” which opens nationwide on September 29th, Gillespie continues his exploration of outsiders. The film, based on Ben Mezrich’s book “The Antisocial Network,” tells the true story of the GameStop short squeeze orchestrated by Reddit-inspired DIY investors. Gillespie injects rebellious energy into the film with fast-paced storytelling, witty humor, and hip-hop music.

Lauren Schuker Blum, co-writer of “Dumb Money,” believes that Gillespie’s own life story aligns with the films he creates. She comments, “Ordinary people who find themselves in extraordinary circumstances and rise to the occasion? That is also Craig’s life story.”

Gillespie did not pursue formal film education, choosing instead to learn on the job by observing commercial directors and experimenting with a handheld camera. He earned his first Directors Guild of America nomination for commercial direction in his early thirties, and won the award two years later. His first feature films, “Mr. Woodcock” and “Lars and the Real Girl,” were released within a month of each other, showcasing the range of Gillespie’s talents.

Gillespie admits that “Mr. Woodcock” did not meet his expectations, attributing this to his lack of control on the set. However, the experience allowed him to approach “Lars and the Real Girl” with a more collaborative mindset, working closely with Gosling to create a successful film. Gillespie believes that failure teaches much more than success, and his early missteps were instrumental in his growth as a filmmaker.

After missing out on the opportunity to work with Gosling on “Dallas Buyers Club,” Gillespie found himself making films that didn’t resonate with him personally. It wasn’t until “I, Tonya” that he returned to his true style and regained critical acclaim. “Cruella” further solidified his reputation as a director who combines drama and comedy in an irreverent and compelling way.

Following the collapse of a film financing deal, Gillespie teamed up with Blum and Angelo once again for “Dumb Money.” The film explores the GameStop phenomenon through the eyes of Keith Gill, the live streamer who played a key role in the stock’s rise, and the community of amateur traders on the WallStreetBets subreddit. Gillespie’s personal connection to the story, through his son’s involvement in GameStop investing, added a deeper level of understanding and authenticity to the film.

Gillespie’s upbringing, which included a strong sense of humor, greatly influences his filmmaking style. He believes that life is a mix of drama and comedy, and strives to capture that balance in his work.

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