It's 1977 and former counterculture hero and famed protestor Abbie Hoffman (VINCENT D'ONOFRIO) has been "underground" for five years. Sensing that he's running out of places to hide, he calls journalist David Glenn (ALAN VAN SPRANG) to do a story on him, hoping to expose what he claims is the government's various measures to harass and/or silence him.
Interviewing Hoffman, his wife Anita (JANEANE GAROFALO) and his lawyer Gerry Lefcourt (KEVIN POLLAK), Glenn begins to piece together the protestor's life, from his involvement in registering African-Americans to vote to his various protests of the Vietnam war with fellow activists Jerry Rubin (KEVIN CORRIGAN), Stew Albert (DONAL LOGUE) and Tom Hayden (TROY GARITY).
As the events chronologically unfold through flashbacks, we see Hoffman becoming more influential and powerful, all of which brings about close government scrutiny under various Presidential administrations. When their measures eventually force him to go "underground," he loses physical contact with Anita and their son, becomes increasingly paranoid and eventually meets Johanna Lawrenson (JEANNE TRIPPLEHORN), whom he takes as a lover.
With the years passing, Hoffman tries to lead a normal life under the assumed name of Barry Freed, but he can't suppress his activist roots and longings. As Glenn's story is eventually published, Hoffman must decide how he wants to live his life.