Jill Hennessy Cast in Showtime Pilot 'City on a Hill'

She is among seven new actors joining Kevin Bacon and Aldis Hodge in the drama pilot from Matt Damon and Ben Affleck.
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Jill Hennessy

Showtime’s drama pilot City on a Hill is rounding out its cast.

Jill Hennessy has been cast in the pilot starring Kevin Bacon and Aldis Hodge. Kevin Chapman, Jere Shea and Lauren E. Banks have also joined the cast. All four will be series regulars if the pay cable network moves forward with the project. In addition, Cathy Moriarty, Michael O’Keefe, Amanda Clayton and Rory Culkin have booked guest roles on the pilot and will recur if it goes to series.

The hourlong pilot takes place in the early 1990s, when Boston was rife with violent criminals emboldened by local law enforcement agencies in which corruption and racism was the norm. Then it all suddenly changed. City on a Hill is a fictional account of what was called the “Boston Miracle.” The change agent is District Attorney Decourcy Ward (Hodge), who comes from Brooklyn and forms an unlikely alliance with a corrupt yet venerated FBI veteran, Jackie Rhodes (Bacon), who is deeply invested in maintaining the status quo. Together they take on a family of armored car robbers from Charlestown in a case that grows to encompass and eventually upend Boston’s citywide criminal justice system.

Hennessy will play Jenny Rhodes, the feisty wife of Jackie who has her own agenda, while Chapman has been cast as Dickie Minogue, a Boston cop who comes into conflict with Jackie. Shea will take on the part of Hank Signa, an investigator for the Suffolk County DA who works with Ward, and Banks will play the part of Siobhan Quays, an attorney who is the wife of Ward. Siobhan grew up in a wealthy family, and that sometimes causes friction in their marriage.

In addition, Moriarty has been cast as Ma Ryan, the doting mother of Frankie (Jonathan Tucker) and Jimmy (Mark O’Brien), who is too easy on Jimmy and too tough on Frankie. O’Keefe will play Agent Clasby, a retiring FBI agent and former partner of Jackie. Meanwhile, Clayton will play Cathy Ryan, the warm but tough wife of Frankie, and Culkin has been cast as Clay Roach, an informant who works for Jackie.

City on a Hill is executive produced by Ben Affleck, Matt Damon and Jennifer Todd (Jason Bourne) for Pearl Street Films. It will be written and executive produced by Chuck MacLean (Boston Strangler), and directed and executive produced by Michael Cuesta (HomelandAmerican Assassin). Produced by Showtime, the project is based on an original idea by Affleck and MacLean. James Mangold (Logan, Walk The Line) will also serve as executive producer, with Bacon serving as co-executive producer. Production will begin later this year in Boston.

Hennessy starred on the long-running series Crossing Jordan and co-starred on such shows as Law & Order and Las Vegas, in addition to appearances on Shots Fired, Madam Secretary, The Good Wife and Luck. Her film credits include RoboCop 3 and Most Wanted. She is repped by APA.

Chapman has co-starred on such series as Brotherhood and Person of Interest, with recurring roles on Sneaky Pete, Rescue Me24 and Lost. His film credits include Unstoppable, Mystic River and In the Bedroom. He is repped by Talent Works and Vanguard Management Group.

Nominated for a Tony Award for Passion, Shea’s screen credits include Southie and Law & Order. He is repped by Cornerstone.

Banks’ credits include Instinct and Safe House: A Christian Story. He is repped by CAA.

Nominated for an Academy Award and Golden Globe for her film debut in Raging Bull, Moriarty’s credits include Patti Cake$, Analyze That, But I’m a Cheerleader, Casper and Soapdish, as well as Showtime’s dramedy I’m Dying Up Here. She is repped by Innovative, Justice & Ponder and Felker Toczek Suddleson Abramson.

O’Keefe has appeared on Masters of Sex, Homeland, Sneaky Pete, The West Wing, Law & Order, The Closer, House and Roseanne, as well as in the feature films The Great Santini, Michael Clayton, Ironweed and Caddyshack. He is repped by Paradigm.

Clayton starred on If Loving You Is Wrong and has also appeared on NCIS: Los Angeles, Major Crimes and Rizzoli & Isles. He is repped by Abrams Artists and Kind Management.

Culkin’s credits include Sneaky Pete, Law & Order: SVU, Gabriel, Igby Goes Down and You Can Count on Me. He
is repped by Paradigm.