Mamet (Glengarry Glen Ross, Oleanna, Speed-the-Plow) will direct his intense drama about "two powerful women forced to engage in a cage match of wits."
The 90-minute play casts LuPone (Evita, Gypsy) as Cathy, a longtime inmate with ties to a violent political organization, who pleads for parole from the warden, Ann, to be played by Winger.
LuPone has a long history with Mamet. The two first worked together on his drama The Woods in 1977. LuPone's Mamet appearances also include The Water Engine, Edmond, The Old Neighborhood and the film "State and Main."
The Anarchist marks Winger's Broadway debut. She is a three-time Academy Award nominee for "Terms of Endearment," "Shadowlands" and "An Officer and a Gentleman."
The Anarchist will have scenic and costume design by Academy Award winner Patrizia Von Brandenstein and lighting by Tony Award winner Jeff Croiter.