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The band generated political controversy by performing before the outbreak of violent protests at the 1968 Democratic National Convention in Chicago. Kramer reported that while many musicians were scheduled to perform at a day-long concert, only the MC5 initially appeared. The MC5 played for over eight hours straight; of the other scheduled performers, Kramer stated  Neil Young actually arrived, though due to the chaos at the convention, Young didn't perform. Dennis Thompson asserted years later that "Country Joe" McDonald (Country Joe and the Fish) was also present at the scene . Other performers at the convention included the protest folk singer Phil Ochs.

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MC 5's manager  John Sinclair  was sentenced to 10 years in prison in 1969 after giving two joints of marijuana to an undercover narcotics officer. This sentence sparked the landmark "Free John Now Rally" at Ann Arbor's Crisler Arena in December 1971. The event brought together a who's-who of left-wing luminaries, including pop musicians John Lennon (who recorded the song, "John Sinclair" on his Some Time in New York City album), Yoko Ono, David Peel, Stevie Wonder, Phil Ochs and Bob Seger, jazz artists Archie Shepp and Roswell Rudd, and speakers Allen Ginsberg, Abbie Hoffman, Rennie Davis, David Dellinger, Jerry Rubin, and Bobby Seale. Three days after the rally, Sinclair was released from prison when the Michigan Supreme Court ruled that the state's marijuana statutes were unconstitutional.