Cooper Raiff: The Young Filmmaker Who Turned a College Movie Into a Career

From making a tiny film with college friends to directing Cha Cha Real Smooth and creating Hal & Harper, Cooper Raiff built his career by writing personal stories and taking unusual creative risks.

0 10 10 minutes read

Introduction

Cooper Raiff is an American filmmaker, writer, actor, producer, and director known for Shithouse, Cha Cha Real Smooth, and Hal & Harper.

Table of Contents

His start was unusually simple.

He made a small movie in college. Then he sent it directly to filmmaker Jay Duplass. That move helped open a completely new path.

Raiff later left college. He focused on filmmaking instead.

It worked.

His first major feature won at SXSW. His second won an audience award at Sundance. Since then, he has moved into television and taken acting roles in projects directed by other filmmakers.

As of 2026, his recent screen work includes See You When I See You and All That She Wants.

Quick Facts About Cooper Raiff

Fact	Details
Name	Cooper Raiff
Profession	Filmmaker, writer, director, actor, producer
Birthplace	Dallas, Texas, United States
Nationality	American
School	Greenhill School
College	Occidental College
College field	Media Arts and Culture
College status	Left before completing his degree
Breakthrough film	Shithouse
Known for	Shithouse, Cha Cha Real Smooth, Hal & Harper
Production company	Small Ideas
2026 acting work	See You When I See You, All That She Wants
Instagram	@coop_myself

Who Is Cooper Raiff?

Cooper Raiff works across several parts of filmmaking.

He writes. He directs. He acts.

He has produced his own work too.

That combination became clear very early. Instead of waiting for a studio role, Raiff began making his own material with friends.

Actually, that DIY start matters.

His early work led directly to Shithouse. That film gave him his first large industry break and put his name in front of a much wider audience.

He followed it with Cha Cha Real Smooth. The film pushed his career further and brought Apple into the picture.

Then came something bigger.

Raiff moved into episodic storytelling with Hal & Harper, an eight-part series featuring Lili Reinhart and Mark Ruffalo.

Early Life in Dallas

Raiff grew up in Dallas, Texas.

He attended Greenhill School in Addison. Acting had already caught his interest during his school years.

He took part in theater.

He also studied acting while young.

Basketball mattered too. Raiff has spoken publicly about playing the sport and sharing that interest with his father.

Movies were part of home life.

He has talked about going to the Angelika Film Center in Dallas with his mother. Those experiences came before filmmaking became his profession.

Some parts of his later work also pull from feelings he knew personally: leaving home, family relationships, growing up, and trying to figure out what adulthood actually looks like.

Education at Occidental College

Raiff later moved to Los Angeles.

He enrolled at Occidental College.

There, he studied Media Arts and Culture.

College changed things fast.

During spring break in 2018, Raiff stayed around campus and made a small film called Madeline & Cooper.

The setup was basic.

A few friends helped.

The budget was tiny.

Raiff later described the project as costing only a few hundred dollars. It was shot within days rather than months.

He put the film online.

Then came the bold part.

How Jay Duplass Found Him

Raiff wanted filmmaker Jay Duplass to watch his movie.

So he contacted him online.

The message basically challenged Duplass to click the YouTube link and respond.

Duplass actually did.

That contact changed Raiff’s career.

The two met and talked about filmmaking. Duplass became an early mentor and encouraged him to keep working on the story.

Raiff then began turning his homemade college film into a professional feature.

That feature became Shithouse.

Why Cooper Raiff Left College

Making Shithouse required a serious choice.

Raiff left Occidental College before graduating.

He was around 22 when he committed himself to the project.

There was no guaranteed result.

Still, he went ahead.

Forbes later listed him as an Occidental College dropout, while the college itself has written about his decision to leave and make his first feature.

That risk became the base of his professional career.

Shithouse and His First Big Break

Shithouse arrived in 2020.

Raiff wrote and directed the film.

He played Alex Malmquist too.

The story follows a homesick college freshman struggling to settle into life away from home. He develops a connection with his resident assistant, Maggie, played by Dylan Gelula.

The film stayed close to Raiff’s own emotional interests.

Homesickness. Connection. Awkward conversations.

Small moments carry the story.

Then the film reached SXSW.

The physical 2020 festival was disrupted during the COVID-19 pandemic, but Shithouse still won the SXSW Grand Jury Award for Narrative Feature.

That changed his position quickly.

He was no longer simply a college filmmaker with an online movie. He now had an award-winning feature carrying his name as writer, director, and actor.

Cha Cha Real Smooth

His second feature came in 2022.

Cha Cha Real Smooth starred Raiff alongside Dakota Johnson.

He wrote, directed, produced, and acted in the film.

The story follows Andrew, a recent college graduate who moves back home and starts working as a party starter at bar and bat mitzvah celebrations.

He then meets Domino.

Dakota Johnson plays her.

Their relationship forms much of the film’s emotional center.

Vanessa Burghardt plays Domino’s daughter Lola. Leslie Mann, Brad Garrett, and Raúl Castillo also appear.

The party setting had personal roots.

Raiff grew up around many Jewish classmates in Dallas and attended numerous bar and bat mitzvah celebrations during school.

He used those memories while building Andrew’s world.

Dakota Johnson’s Role

Dakota Johnson became important behind the camera too.

She worked as a producer.

Raiff had initially not been set on playing Andrew himself. Johnson and producer Ro Donnelly encouraged him to take the part after seeing his work in Shithouse.

That choice became part of the finished movie.

The film premiered at Sundance in 2022.

It won the U.S. Dramatic Audience Award.

Apple then acquired worldwide rights in a reported $15 million deal.

That was a huge jump.

A filmmaker who had recently made a college project with friends now had his second feature acquired by one of the world’s biggest technology and entertainment companies.

Small Ideas Production Company

Raiff later expanded into producing.

He co-founded Small Ideas with producer Clementine Quittner.

The company was built around filmmaker-led projects and independent production.

This became especially useful with Hal & Harper.

Rather than letting the series change into something he no longer wanted to make, Raiff took the project back and pursued an independent route.

That choice kept creative control closer to the people making it.

Hal & Harper

Hal & Harper became Raiff’s first major episodic project.

The limited series was released in 2025.

It runs for eight episodes.

Raiff created, wrote, directed, and starred in it.

Lili Reinhart plays Harper.

Raiff plays Hal.

Mark Ruffalo plays their father.

The cast also includes Betty Gilpin, Havana Rose Liu, and Addison Timlin.

The story follows adult siblings Hal and Harper, whose close bond is tied to difficult experiences from childhood.

It moves between different periods of their lives.

Raiff and Reinhart even play younger versions of their characters.

That unusual choice gives the story a distinct feel.

Why Hal & Harper Took Years

The idea was not new.

Raiff had versions of Hal and Harper in mind years before the finished series appeared.

Early versions existed around his college years.

He kept returning to them.

The project was once set up at FX, according to Raiff. He later felt it was being pushed toward a different kind of college-focused show.

He asked to take it back.

Then he made it independently.

The finished series premiered at Sundance in 2025 and later became available through MUBI.

His Work as an Actor

For years, Raiff was most closely tied to characters he had written himself.

That has started changing.

In 2026, he appeared in See You When I See You, directed by Jay Duplass.

Yes, the same Jay Duplass.

The connection had come full circle.

Raiff plays Aaron in the film.

The cast includes Kaitlyn Dever, David Duchovny, Hope Davis, Lucy Boynton, and Ariela Barer.

The story is based on Adam Cayton-Holland’s memoir Tragedy Plus Time.

It premiered at the 2026 Sundance Film Festival.

For Raiff, the role marked another move toward acting in material written and directed by other people.

All That She Wants

Another 2026 project is All That She Wants.

Raiff stars opposite Annie Murphy.

He plays Luke.

The romantic comedy follows Emma, played by Murphy, after she meets a younger man and later realizes she once babysat him when he was an infant.

The supporting cast includes Christine Baranski, Zosia Mamet, John Gemberling, Finn Wittrock, and Bill Irwin.

The film premiered during the 2026 Toronto International Film Festival.

Raiff attended its TIFF premiere on September 13, 2026.

That makes it one of his freshest public projects as of September 2026.

The Trashers

Raiff was previously attached to direct The Trashers.

The planned project concerned the Danbury Trashers minor-league hockey story.

David Harbour, Cooper Hoffman, and Olivia DeJonge were connected to the film.

Raiff was especially interested in its father-son relationship.

The project did not move ahead as planned.

By 2025, he had publicly discussed its financing problems.

For that reason, The Trashers should not be described as a confirmed upcoming Cooper Raiff film.

Cooper Raiff’s Filmmaking Style

His stories often stay close to people.

Big action is rarely the point.

Conversation matters more.

So do uncomfortable silences.

Characters often sit between two stages of life. A student leaves home. A graduate returns home. Adult siblings face childhood pain they never fully left behind.

That pattern appears repeatedly.

Raiff also mixes humor with sadness.

One scene can feel funny.

The next gets uncomfortable.

Sometimes both happen together.

His work has also been linked with filmmakers such as Jay Duplass and Richard Linklater, while Raiff has spoken positively about Sofia Coppola’s Lost in Translation.

Movies and TV Work

Year	Title	Main Role
2018	Madeline & Cooper	Writer, director, actor
2020	Shithouse	Writer, director, producer, actor
2022	Cha Cha Real Smooth	Writer, director, producer, actor
2025	Hal & Harper	Creator, writer, director, producer, actor
2026	See You When I See You	Actor
2026	All That She Wants	Actor

Awards and Career Recognition

Shithouse won the SXSW Grand Jury Award for Narrative Feature in 2020.

Cha Cha Real Smooth won the U.S. Dramatic Audience Award at Sundance in 2022.

Raiff was also selected for Forbes’ 30 Under 30 Hollywood & Entertainment list.

His Cha Cha Real Smooth screenplay received the Humanitas Prize for Comedy Feature Film in 2023.

Those wins arrived early.

But they also came from projects where Raiff handled several jobs himself.

Cooper Raiff and Addison Timlin

Raiff publicly confirmed a romantic relationship with actress Addison Timlin in 2025.

Timlin also appears in Hal & Harper.

In a PEOPLE interview published in 2025, Raiff spoke warmly about their relationship and referred to Timlin as his person.

There is a simple way to report this accurately.

The relationship was publicly confirmed in 2025.

Claims about their private status after that point should not be guessed without newer confirmation.

Is Cooper Raiff Married?

There is no reliable public confirmation that Cooper Raiff is married.

So claims naming a wife should be avoided.

The publicly documented relationship with Addison Timlin is the safer fact to use.

Cooper Raiff’s Family

Raiff has discussed his family in interviews.

He has spoken about being close to his mother.

He has also discussed playing basketball and bonding with his father through the sport.

His family experiences have fed into parts of his writing.

Still, detailed private family information is limited.

That is worth respecting.

Names and personal details repeated only by low-quality celebrity sites should not be treated as fact.

Cooper Raiff Net Worth

There is no reliable public figure for Cooper Raiff’s personal net worth.

Many websites publish estimates.

Those numbers are not backed by public financial records.

A reported $15 million Apple acquisition for Cha Cha Real Smooth does not mean Raiff personally received $15 million.

The money relates to film rights.

It is not his personal net worth.

So a specific wealth estimate would be misleading.

Where Is Cooper Raiff Now?

Raiff remains active across filmmaking and acting.

His work has changed quite a bit.

He began with tiny self-made projects.

Then came independent features.

After that, television.

Now he is also taking lead acting roles in films directed by other people.

Hal & Harper remains one of his biggest personal projects, while See You When I See You and All That She Wants represent his recent acting work in 2026.

That is where his career stands right now.

Final Thought

Cooper Raiff took an unusual route.

He did not wait around.

He made something small instead.

That college project reached Jay Duplass, became the starting point for Shithouse, and helped turn Raiff into a working filmmaker.

Then the scale grew.

Cha Cha Real Smooth brought Sundance success and an Apple deal. Hal & Harper moved him into television. His 2026 roles show another side of his career: acting in stories that are not his own.

The interesting part is simple.

He keeps changing the job.

Writer. Director. Actor. Producer.

Sometimes all at once.