Hill's first film, The Foot Fist Way, was seen by Will Ferrell and Adam McKay who bought the distributing rights to the film. Subsequently, Hill was invited to the set of Knocked Up where he met future collaborator, Seth Rogen. Hill was asked to do a cameo appearance with writing partner Ben Best in Rogen's next film, Superbad, as Tut Long John Silver. Hill later cast Rogen as the leading man in his film, Observe and Report, which opened at number 4 at the box office. The role of Ronnie was written specifically for Rogen.
In 2009, Hill directed The Avett Brothers music video "Slight Figure of Speech," which featured Wolfe and Andy Daly.[citation needed] The following year he directed the parody music video Swagger Wagon as part of ad agency Saatchi & Saatchi's campaign for the Sienna SE minivan from Toyota.
In 2009, Hill co-created the HBO show Eastbound & Down, on which he acted as Executive Producer and directed a total of 16 episodes. The show finished its fourth and last season in 2013.

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