How Cooper Raiff tricked Hollywood and started a new era (2024)

Over the years, there have been some truly inspirational stories on how people found success and wormed their way through the impenetrable fortress that is Hollywood, from accidental meetings in supermarkets, spontaneous auditions, or the increasingly popular backstory of simply being related to someone who sits behind the camera. But few people in the industry have a story as interesting as Cooper Raiff, the young filmmaker who forged his own path in the most unlikely way, going from a nano-budget short to a multi-million-dollar feature in less than two years. So how did he do it?

The landscape of independent cinema is currently the most hostile and unforgiving it’s ever been, with low-budget filmmaking becoming unfeasible and being overshadowed by the gargantuan studios that churn out a constant stream of creative sludge. The filmmakers that used to thrive on no money in the mumblecore era steadily ditched this model after being lured away by the prospect of complete creative freedom, which is ultimately hollow given that they have to cater to the suits that finance them. With all of this, it’s a miracle when any emerging or aspiring filmmaker is able to rise above the bullshit and get anything made, something that Raiff was able to do when he was only 20 years old.

During his freshman year of college, Raiff had a classically awkward rite of passage experience that inspired him to make a 50-minute short film called Madeline and Cooper, following an attempted one-night stand that ends in the pair becoming best friends. While all his fellow classmates were visiting home over the spring break, Raiff decided to stay on campus and make a film, pulling all his friends and resources together to make what nearly qualifies as a feature film. He’d always loved acting but hadn’t expected to find himself both in front and behind the camera, with Raiff also starring in the entrepreneurial short. The credits resemble that of a Neil Breen film, with Raiff’s name endlessly plastered in front of each role, which could come across as slightly narcissistic from any other filmmaker, but in Raiff’s choice, he really didn’t have a choice. After making it, he pondered on the best way to share it and spontaneously decided to tweet a link to fellow director and mumblecore icon Jay Duplass, saying, “I bet you won’t watch this…”.

For many people, this would be the end of the story; you hopefully and slightly pathetically share your work with a bunch of people and wait as the metaphorical tumbleweed fills your inbox, feeling expectedly sad when no one discovers you and conveniently changes your life. But for Raiff, Duplass actually replied, saying that he loved the film and wanted to meet. It’s the kind of miraculous luck that almost never happens. Raiff obviously agreed, and when the pair met in person, Duplass encouraged him to make a feature-length version of the film. Raiff took his advice and dropped out of college in 2019 to focus on making the film, raising some money via a Kickstarter fund that Duplass personally shared on social media, eventually shooting the feature-length version called Shithouse in 2020.

The pandemic slightly delayed the release of the film, but it was finally premiered at the infamous South by Southwest Festival, winning the Grand Jury prize for ‘Best Narrative Feature’ and being acquired for distribution by IFC Films, who later changed the name to Freshman Year (you can’t win em’ all). And through the success of this one film, Raiff catapulted to success and became one of the most sought-after emerging directors in Hollywood shortly after being offered an exclusive million-dollar deal with Apple TV for his next project, Cha Cha Real Smooth. Raiff has been consistently working ever since, recently shooting an original series of Amazon Prime with Phoebe Dynevor and an upcoming feature film called The Trashers starring David Harbour and Cooper Hoffman.

There are not many people with a story like this, bypassing the usual levels of countless interviews, entry-level jobs and shitty assistant gigs before even getting a toe in the door. There is no doubt that Raiff is extremely talented, but like many people, his story relied on equal parts skill and luck. In an industry that hinges on interpersonal connections, generational wealth and elitism, Raiff simply happened to message the right person at the right time and found himself a hop, skip and jump away from the kind of success people don’t dare to dream of.

Hope in this industry can feel painful, like a double-edged sword that reminds you of a fading future you so desperately want, but realistically, know the odds are stacked against your success. Hollywood will break the hearts of most people who attempt to be a part of it, but Raiff managed to sidestep the tragic years of yearning and pining and skip to the ultimate step of making. It gives new hope to the struggling artists and makers who journey on the same treacherous path, even if it’s a road to nowhere for most of us.

But even with this, I have little hope that this will open doors or reinvigorate the industry’s approach to emerging talent. The people at the heart of Hollywood are unwilling to let new people into the club, preferring for talent to be presented on a silver platter without looking for it themselves; they wait for one success story and then pounce, awarding them every available opportunity and closing the doors for anyone else. Hollywood’s existence thrives on exclusivity, and they don’t want to let new people in, so it works in their favour to find one person and pin their name onto every project so they appear to be accessible.

All truth be told, I think the story of Cooper Raiff is a once-in-a-lifetime anomaly – cases like this are increasingly rare and fantastical. It’s a bedtime story for dreamers and a lifeline for desperate creatives. It’s the kind of rags-to-riches story that Hollywood only accepts once every blue moon before locking the gates. Raiff is a success, but mark my words, his success story will be used to justify the exclusion of hundreds of other talented emerging filmmakers who are dying for the same chance, with the slimy executives patting themselves on the back for letting one person into the club who didn’t previously belong, and after that, call it a day. The vague statements about prioritising new talent and diversity are completely empty because I ask you this – name one other person in recent years who’s had a story like Cooper Raiff?

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