Pierce's first job was as a forest ranger for the Commonwealth of Massachusetts. He wrote for Worcester Magazine in the 1970s, where he covered the Blizzard of 1978. In the 1980s and '90, he was a staff reporter for the Boston Phoenix and, later, a sports columnist for the Boston Herald.
Pierce is currently the lead political blogger for Esquire, a position he has held since September 2011. He also wrote for ESPN's Grantland. He has also written for The New York Times, the Los Angeles Times, the Chicago Tribune, the Boston Globe Sunday magazine, the Milwaukee Journal-Sentinel, Sports Illustrated, The National Sports Daily, GQ, and the e-zine Slate as well as the Media Matters blog Altercation, hosted by historian/pundit Eric Alterman.
Pierce makes appearances on radio as a regular contributor to NPR programs Only A Game and Wait Wait...Don't Tell Me!. Recently Pierce has begun making weekly appearances on the Stephanie Miller Show. He represented the Globe on several occasions on ESPN's Around the Horn and often co-hosts with Bob Ryan on NESN's Globe 10.0.
Pierce has written four books:
- Sports Guy (2000) ISBN 978-0-306-81005-3
- Hard to Forget: An Alzheimer's Story (2000) ISBN 978-0679452911
- Moving the Chains: Tom Brady and the Pursuit of Everything (2006) ISBN 978-0374214449
- Idiot America: How Stupidity Became a Virtue in the Land of the Free (2009) ISBN 978-0767926140
- "Sports guy : in search of corkball, warroad hockey, hooters golf, Tiger ..." Library of Congress Online Catalog. Retrieved March 28, 2017.
- "30 Years of Worcester Magazine". Worcester Magazine. 2006-04-27. Archived from the original on 2006-06-23.
- Charles P. Pierce (2008-11-26). "Football, Hold the Stuffing". The Daily Beast. Retrieved 2012-01-29.
- "Charles P. Pierce". Charles Pierce.
- "About the Panelists". National Public Radio.
- Chet Williamson (2008-02-21). "30th Anniversary: Blizzard of '78". Worcester Magazine. Archived from the original on 2008-07-05.
- Look Out, America: Charles P. Pierce Is Coming to This Blog
- The Stupidity (and Sexism) of Baseball's Media Dress Codes
- Pierce, Charles. "The Civility Debate Has Reached Peak Stupidity". Esquire. Retrieved 26 June 2018.