Originally from Los Angeles, Rossen moved to attend New York University. Rossen is the grandchild of filmmaker Robert Rossen, who directed The Hustler and All the King's Men. Robert Rossen's parents were Russian-Jewish immigrants. As a student at the university, Rossen formed Department of Eagles with roommate Fred Nicolaus in 2001. The duo then released two 7" singles and an album, The Whitey on the Moon UK, on Isota Records. About Department of Eagles early recordings, Rossen explains:
Rossen concurrently went on to join Grizzly Bear in 2005. He joined the group for their second album, Yellow House. On joining Grizzly Bear, Rossen notes:
Department of Eagles released their second record In Ear Park in October 2008. The album featured fellow Grizzly Bear bandmates Chris Taylor and Christopher Bear of Grizzly Bear, with Taylor co-producing. The album was dedicated to Rossen's late father, with whom Rossen shared memories of going to the titular park.

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