Film
While still at NYU, Wolf worked with the video activist collective Paper Tiger Television, collaborating with queer youth and homeless queer youth on making community-based media.
His first feature documentary, Wild Combination: A Portrait of Arthur Russell , is about the avant-garde cellist and disco producer Arthur Russell. His second feature, Teenage , is about the birth of youth culture, based on a book by the British punk author Jon Savage.
In 2019, he completed his third feature film, a documentary about Marion Stokes titled Recorder: The Marion Stokes Project , [7] . [8] That same year, Wolf co-curated the film program for the Whitney Biennial. [9]
His two-hour documentary on Biosphere 2 titled Spaceship Earth premiered at the 2020 Sundance Film Festival and was released by Neon in May 2020. [10]
Wolf has made a number of short films, including Bayard & Me, about the civil rights activist Bayard Rustin adopting his younger boyfriend for equal rights; I Remember, about the artist and poet Joe Brainard; It’s Me, Hilary, about the Eloise illustrator Hilary Knight; and Another Hayride , about the self-help guru Louise Hay.
In November 2023, Criterion featured Wolf's full filmography on its streaming platform.
In 2025, Wolf's documentary on the life and work of Paul Reubens, titled Pee-Wee as Himself , premiered on the opening night of the Sundance Film Festival. [11] [12] He spent over 40 hours interviewing Reubens, and was given access to the actor's large collection of photographs and video footage. Wolf was unaware that Reubens was battling cancer throughout the production of the doc, which heavily features their contentious struggle over creative control of the project. The film includes a final message from Reubens, recorded the day before his death. The film was nominated for five Primetime Emmy Awards, and won for "Outstanding Picture Editing," "Outstanding Directing," and "Outstanding Documentary." [13]
Writing
In 2025 it was announced that Wolf is writing a book, Trust Me, about the relationship between documentary filmmakers and their subjects for Bloomsbury. [14] He published a first person essay in New York Magazine that same year about his contentious relationship with Paul Reubens while making Pee-wee as Himself . [15]
While working on Recorder: The Marion Stokes Project , Wolf screened 700 hours of archival footage collected by Stokes. In 2023, he compiled a book titled Input, consisting of hundreds of stills from talk shows, local news, and commercials, with an eye for images that were "mysterious, haunting, bizarre, and beautiful to tell an abstract story about our televisual lives."
