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Kilstein is the co-creator of and former director and co-host of Citizen Radio (formerly Drunken Politics), an internet political radio show, which Kilstein and co-host writer Kilkenny describe as "being like CNN, but with more swearing." Guests during his time hosting included Noam Chomsky, Ralph Nader, Bad Religion, Sarah Silverman, Janeane Garofalo, Glenn Greenwald, Naomi Klein, Chris Hannah, Howard Zinn, and Rachel Maddow. On February 27, 2017, Kilstein announced on that day's Citizen Radio episode that he was leaving the show. Later that day his cohost and ex-wife Allison Kilkenny announced via Facebook that Jamie had been removed from the show due to "disturbing allegations" of "manipulative, emotionally abusive and predatory behavior" concerning women associated with the show.

In 2015, Kilstein announced a Pledgemusic campaign for his musical project, Jamie Kilstein and the Agenda. The band's debut record, A Bit Much, was released by Don Giovanni Records on July 22, 2016.

He and Kilkenny (his Citizen Radio co-host and wife at the time) wrote the book Newsfail, which was released on October 14, 2014. The book covers topics including Palestine, trans rights, feminism, atheists, and factory farming.

Kilstein's fourth comedy album, What Alive People Do, was released on October 22, 2013. It was a double album recorded in front of an Austin audience at the New Movement Theater on December 2, 2012.

Kilstein's writing has appeared on left-leaning sites including Wonkette, which featured a recurring column in summer 2012 titled Sundays with Jamie Kilstein and the Lord. The column covered topics like pundits' penchant for overusing 9/11 analogies and "anchor babies". In September 2013, Kilstein came out publicly as suffering from both alcoholism and an eating disorder in a front-page article for Jezebel, "I'm an Alcoholic Dude With an Eating Disorder. Hi."

Kilstein made his U.S. debut TV appearance on February 2, 2011, on the talk show Conan, on which he performed a stand-up routine critical of continued involvement in the Iraq War.

Kilstein's first comedy album, Please Buy My Jokes, was recorded on February 23, 2008 in front of a live audience at the Lakeshore Theater in Chicago. It was released in 2008. In actuality, Please Buy My Jokes was a limited edition of two hundred CDs, made from one of the sessions of his actual debut, Zombie Jesus. It was made expressly for Kilstein to sell at the Edinburgh Fringe Festival, and was looked upon by both Kilstein and his record label not as a debut release inasmuch as a stopgap merchandise item for that specific event. The CD was never repressed and never made available digitally. His second comedy album, Zombie Jesus, was also recorded at the Lakeshore Theater in Chicago, on September 11–13, 2008. It was released on October 27, 2009. Kilstein released his third album, Libel, Slander, and Sedition, on September 13, 2011. It was recorded at the Acme Comedy Company in Minneapolis, Minnesota, October 13–16, 2010.

Jamie Alexander Kilstein (born May 17, 1982) is an American writer, radio host, and stand-up comic. He made his debut television appearance on Conan and has been seen on MSNBC's Up with Chris Hayes, Countdown with Keith Olbermann, Showtime, and BBC America. Kilstein previously hosted the internet talk radio show Citizen Radio along with his former wife, political columnist Allison Kilkenny; he left the show after allegations of predatory sexual misconduct against multiple women.