He performed in provocative novelty bands in high school, released prank call CDs, and created xeroxed comics, joke books and zines.

In 2013 Kline wrote and directed the short comedy Fowl Play, about a group of low-rent criminals fooled into buying a hen for a cockfight in Flushing, Queens.

[6] Kline spent six years continually writing, directing and editing his debut feature Funny Pages, a black comedy about a young dropout cartoonist striking out on his own in Trenton, New Jersey.

Produced by the Safdie Brothers and distributed by A24, it premiered in the Director's Fortnight at the 75th Cannes Film Festival in 2022.

[7] Prior to Funny Pages, Kline provided archival research for books, including Mark Newgarden and Paul Karasik's How to Read Nancy.