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 fifteen albums as of 2024. From 2022–24, James hosted the podcast 'All Your Days,' focusing on how creative careers transform over time.
In his professional career, James O'Brien is a senior marketing and advertising consultant with executive-team experience specializing in content-forward projects. Known for providing critical expertise to campaigns of all sizes, leadership consultation during times of significant change and growth, and a blend of empathy and relationship building coupled with a strategic, data-driven approach.
As a filmmaker, James’s documentary about Bob Dylan's unpublished writings has been added to The Bob Dylan Archive in Tulsa, Oklahoma.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 He holds a master's and a Ph.D. in editorial studies; his dissertation focuses on unpublished writings by Bob Dylan.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.
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 and sustainable food initiatives in Sierra Leone.