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 As a filmmaker, James’s documentary about Bob Dylan's unpublished writings has been added to The Bob Dylan Archive in Tulsa, Oklahoma.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.