Independent financing was raised; actors Anthony Stewart Head, Lindsay Felton, and Tanya Roberts were attached to star in the film; and Roddy Bottum (from the band Faith No More) came aboard to provide the musical score.

In 2003, after scripting a straight-to-video release called AfterLife,[2] O’Sullivan began working as a writer for the NBC television network's Peabody and Emmy Award-winning The More You Know series (writing PSA's for such stars as David Schwimmer,[3] Goran Visnjic, Sharif Atkins, Christopher Meloni, Brittany Snow, and Donald Trump).

[5] In early April 2004, O’Sullivan began work on his feature film directorial debut, a low-budget independent comedy about a group of employees in a rock & roll radio station, called Communication Breakdown.

[6] Co-written by O’Sullivan and one of the film's stars, actor Dan Lashley), principal photography took place at the studios of Blue Ridge Motion Pictures in Asheville, North Carolina, wrapping production in early May of that same year.

[7] In 2005, O’Sullivan worked as an Associate Producer on a series of motorsports documentaries featuring the likes of Travis Pastrana (star of MTV's Nitro Circus), Nate Adams, and Andy Bell.

During this same period, he helmed numerous music videos, including ones for such artists as Always Sunday (featuring Trent Dabbs), The Situationals, Rachel Merchand, Judson, Shawn Gallaway, and Randy Casey (formerly of P.J.

On November 3, 2009, it was announced that a romantic comedy script written by O'Sullivan and Lashley entitled One Night With You[12] was being developed for the big screen in association with Scott M. Rosenfelt, producer of such films as Home Alone (1990), Mystic Pizza (1988) and Teen Wolf Too (1987).

[21] After Lohan was forced back into court due to a parole violation in early 2011, O’Sullivan seemed to abandon the plan of proceeding with the beleaguered actress, telling reporters, “We’re screwed.”[22][23] While dealing with the Lohan situation, O’Sullivan also announced plans for two other projects: An original horror film entitled Hallows (later retitled The Ballad of Jimmy Hallows[24])—which was initially conceived as a vehicle for former adult film star Sasha Grey[25][26]—and the dark comedy The Genesis of Lincoln (based loosely on the historical book of the same name about Abraham Lincoln by James H. Cathey).

Attached to The Genesis of Lincoln (a film-within-a-film about a director attempting to adapt Cathey's book, only to be derailed after he has an affair with his underage leading actress) was actor Doug Hutchison, who had, himself, recently married sixteen-year-old pop singer Courtney Stodden.