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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.