After a two-year stint at Shell Oil Company in Bakersfield, California, he left the engineering profession and opened up his first movie theater.

An unmitigated financial disaster, the Tejon theater closed in 1995, and he loaded a truck with 200 seats, a projector, screen, and speakers, and relocated to Austin, Texas, where he launched Alamo Drafthouse Cinema,[2] where he remained as CEO until 2020 when he was replaced by Shelli Taylor.

[citation needed] In 2004, League co-founded entertainment merchandiser Mondo to produce and distribute limited-edition poster art, t-shirts, toys, and vinyl record soundtracks.

[5] In 2005, League, Harry Knowles, Paul Alvarado-Dykstra, and Tim McCanlies co-founded Fantastic Fest, the largest genre film festival in the United States.

Held annually at the Alamo Drafthouse South Lamar in Austin, Texas, the festival focuses on such genres as horror, science fiction, fantasy, action, Asian, and cult.