[1] At Harvard, Oppenheim studied under filmmakers Ross McElwee, Robb Moss, and Guy Maddin, and lived in Adams House.

In college, Oppenheim directed three short documentaries acquired and distributed by The New York Times Op-Docs.

His short The Happiest Guy in the World, about long-term cruise passenger Mario Salcedo, premiered at the Tribeca Film Festival in 2018.

[4][5][6][7] Oppenheim directed and produced his debut feature, Some Kind of Heaven, a documentary exploring life inside The Villages, Florida, as part of his undergraduate senior thesis.

The film was produced by filmmaker Darren Aronofsky and The New York Times, one of the paper's first feature-length productions.