Cooper Raiff

A native of Dallas, Raiff attended the Greenhill School.^[1] He participated in school theatre productions and studied at the Dallas Young Actors Studio for 4 years.^[4] During his senior year, he wrote and performed in his first play.^[5] Raiff enrolled at Occidental College in Los Angeles, withdrawing in 2019 to focus on film.^[6]

During spring break in 2018, Raiff stayed on campus to make Madeline & Cooper, a 50-minute short film that he uploaded to YouTube.^[7] He then tweeted a link of the video to filmmaker Jay Duplass, who met with Raiff and encouraged him to adapt the project to feature-length; it became Raiff's debut feature Shithouse, in which he starred, directed, wrote, produced, and co-edited.^[8] The film premiered at the 2020 SXSW where it was named Best Narrative Feature.^[9] Distributed by IFC Films,^[10] it opened in October 2020 to positive reviews.^[11][12]

In August 2021, it was announced that Raiff was attached to direct and co-write a television adaptation of Naoise Dolan's novel Exciting Times starring Phoebe Dynevor for Amazon Prime.^[13]

Raiff's second film, Cha Cha Real Smooth, premiered at the 2022 Sundance Film Festival, where it won the Audience Award for the Dramatic Competition, and is available on Apple TV+.^[14] The film was reportedly purchased by the company for $15 million.^[15] He appeared on the 2022 Variety list of directors to watch.^[16]

In July 2022, it was announced that Raiff would direct The Trashers, a drama starring David Harbour and Cooper Hoffman.^[17] However, Raiff later revealed in 2025 that the film had been cancelled due to financing issues.^[18]

On August 2, 2022, Raiff partnered with Clementine Quittner of Black Bear Productions to launch his own production company, Small Ideas.^[19] Later that year, he was given the Maverick Award at the 2022 Newport Beach Film Festival^[20] and appeared on the Forbes 30 Under 30 list in Hollywood & Entertainment.^[21]

In 2023, Raiff filmed his first television series, Hal & Harper, starring alongside Mark Ruffalo and Lili Reinhart.^[22]

In October 2024, it was announced that Raiff had been cast as Aaron in the family comedy-drama See You When I See You, directed by Jay Duplass. The film is based on Adam Cayton-Holland's memoir Tragedy Plus Time and co-stars David Duchovny, Hope Davis, and Kaitlyn Dever.^[23] It is set to premiere at the 2026 Sundance Film Festival.

In November 2025, it was announced that Raiff would star opposite Annie Murphy in the romantic comedy All That She Wants.^[24]

Raiff has cited Emma Seligman, Sofia Coppola, Greta Gerwig, Ryan Coogler, and the Duplass brothers as influences.^[25][26]