In 2010, Bossie produced the American documentary film "Generation Zero" for Citizens United Productions, written and directed by Steve Bannon, which attributes in some measure the origins of the financial crisis of 2007–2008 to moral failings of the Baby Boom generation, in particular their turning away from parental values during the countercultural 1960s. Bossie has written several books attacking Democratic rivals, including John Kerry, Bill Clinton, and Hillary Clinton, as well as a political memoir co-authored with Corey Lewandowski concerning Donald Trump's successful 2016 presidential campaign.