James O’Brien toured the U.S. and the U.K. from 1998–2004 playing politically aware songs, sometimes solo and sometimes with a band, sharing billings with artists such as Hamell on Trial, Dan Bern, Michael McDermott, John Sinclair, Bill Miller and Freedy Johnson. In 2017, after a 13-year hiatus, he began to release archival and new material, expanding his catalog to fourteen albums as of 2022. James hosts the podcast 'All Your Days,' which focuses on how creative careers transform over time.
As a filmmaker, James’s documentary about Bob Dylan's unpublished writings has been added to The Bob Dylan Archive in Tulsa, Oklahoma. As of 2020, his award-winning music video — titled "Weaponized" and addressing the topic of mass shootings — is screening at festivals in the United States. In 2022, he was an editorial consultant on the forthcoming authorized documentary about the artist Catherine E. Coulson (‘Eraserhead’ ; ‘Twin Peaks’). He holds a master's and a Ph.D. in editorial studies; his dissertation focuses on unpublished writings by Bob Dylan. Oxford University Press and other publishers have issued his writings about Dylan's work; OUP has published his annotated bibliography of works about the director John Cassavetes.
In his professional career, James O'Brien is an advertising executive specializing in branded and sponsored content, leading and shaping content strategy and campaigns since 2010. He is the president of Custom, the in-house sponsored content agency at Digiday Media. Prior, James has served in formative, consultative editorial roles for content-marketing startups, and he’s led content marketing and executive thought leadership in the ad tech space.
In the years before marketing and advertising, he was a journalist for nearly a decade in the Boston area, building and leading newsrooms at the town and city levels, including writing for a half-decade (2008-2012) as a statewide stringer for The Boston Globe, including page-one stories.
Since 2016, James has volunteered for The Resolution Project, mentoring a social entrepreneurship project creating new access to women's health services in Kenya.