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Exclusive Interview: Jill Hennessy on the heartbreak and healing for Jenny in Season 2 of City on a Hill

Kevin Bacon and Jill Hennessy
Kevin Bacon and Jill Hennessy in City on a Hill. Pic Credit: Eric Ogden/Showtime

It’s Boston 1993 when we return to City on a Hill on Sunday night. The story for the second season centers on a federal housing project in the Roxbury neighborhood of Boston plagued with drug violence and a justifiable distrust of local law enforcement.

But it wouldn’t be City on a Hill without the machinations of irreverent FBI agent Jackie Rohr (Kevin Bacon) and assistant district attorney Decourcy Ward (Aldis Hodge), who continue their adversarial roles, and quickly get involved with the goings-on in Roxbury, which leads to an all-out war between the offices of the U.S. Attorney and the Suffolk DA.

But this season, the women in their lives also play a big role in the story: From coalition leader Grace Campbell (Pernell Walker), who works tirelessly on behalf of the Roxbury community; to Decourcy’s wife Siobhan (Lauren E. Banks), a successful attorney at a private firm; as well as Jenny Rohr (Jill Hennessy), wife of Jackie, who is just coming back from hitting absolute rock bottom in terms of the sexual abuse she endured as a kid from her own father, and really opening her eyes to what is happening to her in her relationship with her cheating husband.

“What’s exciting about playing her, to be honest, is there is this fresh joy,” Hennessy tells Monsters & Critics in this exclusive interview. “She is going through this bizarre [second] childhood where she is suddenly realizing, ‘Gee, maybe I don’t have to blame myself for all the bad things in my life, and maybe I can take responsibility and choose what’s healthy, what’s not dysfunctional.’ She is putting pieces together and trying and failing and trying and failing and succeeding.”

There is a tear-jerking scene in the second episode where Jenny screws up her courage and decides to pursue her interest in singing. While she is waiting in the reception area of a music teacher’s office, a young girl makes a comment to her that sends her running from the office once again suffused with doubts.

“Just reading that scene broke my heart, and you see how quickly that happens to all of us in those opportunities where you are trying something you love for the first time, but you are afraid and nervous, and what if I’m not good enough?” Hennessy says. “And then it just takes the least little push to knock you off your feet and hide and never try it. But it also doesn’t mean you can’t try again. I think we’ve all had moments like that in our lives. I know I have.”

For Jenny to assuage her self-doubt, she heads to church, where she sits in the vast emptiness and consoles herself by singing a religious song. It starts quietly, just to herself, but as her confidence returns, she sings loud enough to fill the space.

“It’s her trying to get past hating herself, to get past judging herself, especially after having been judged so harshly her whole life by both her mother and father, and also not acknowledged when she tried to communicate that she was being abused,” Hennessy explains. “Her mother not only ignoring that but verbally abusing her for that or blaming her, and then shutting something down in herself for basically the rest of her life.”

The singing in church also represents an effort to open the door again to something that gave her such joy as a kid and still does as an adult. It’s why the former Law & Order star loves that moment, but it also takes her back to something that happened in the first grade. Hennessy recalls wanting to try out for the track team, so her parents bought a new pair of green shorts, which she wore on the big day, but then she lost her nerve.

“At the tryouts, there are all these kids and they’re in great shape in these awesome Adidas outfits and stuff and I literally turned around and left, and I never told my parents that I didn’t try out,” she shares. “To this day, it still bothers me that I didn’t try out for the track team, but literally, I tried out the next year. It taught me something. It’s always baby steps, man. You take a couple of steps backwards, but then you make a whole bunch of strides forward.”

Jill Hennessy in City on a Hill
Jill Hennessy in City on a Hill. Pic Credit: Francisco Roman/Showtime

Jenny is trying to do the same for her and Jackie’s daughter Bendetta (Zoe Margaret Colletti), who had a drug problem in season one and was attacked by two men while under the influence. In Season 2, Jenny feels responsible so she joins Al-Anon to not only help herself but to try to be more equipped to communicate with her daughter. But even so, when Benny comes to her mother to make amends after getting out of rehab, Jenny at first refuses to let her speak.

“I think it is a sense of guilt,” Hennessy says. “I think that’s what happening in that scene. Jenny’s having such a difficult time, not wanting her daughter to have to go through the pain of having to make an amends, especially, because she feels it is all her fault anyway, so her daughter has nothing to make amends for.”

But then Jenny she catches herself and realizes, “This is part of her therapy, part of her program. I have to let my daughter do that.” So, she tries to wind her way through what 12-step programs are, what healing yourself is all about, and being open to her daughter’s path as well as her own.

Hennessy also talked to M&C about what it is about this era that drew her to the project, her own music background, and more.

Monsters & Critics: This show is set in 1993 when Boston had a lot of issues with corruption, drugs, etc. Is there a lesson in there for today’s audience?

Jill Hennessy: I’ve got to say, man, not much has changed. They are all issues that are alive and well today and not only in Boston but everywhere, especially in terms of race as well as economic disparity.

The writers and showrunner originally took an idea — Chuck McClain went in there with his experience of living in Boston and gave the show such an incredible voice. They took a period of a decade, the ‘90s, which was very emblematic, I think, of American life at large.

It was a fascinating period, and they like to distill it down to the Boston Miracle, but a lot of stuff was going down. So, it is really rich material to draw from and to act.

M&C: Is there a dichotomy in what you just said? You mentioned the Boston Miracle, which is when the city cleaned up a bit. But earlier you said not much has changed.

Jill Hennessy: I don’t know if there is a contradiction. Actually, what is really great about the Boston Miracle was seeing the process of it in these first two seasons. One thing I have heard, too, in my research and studying different journalists at the time and after the fact, is communication opening up between committee activist leaders and the police department, and the prosecutors’ office and weeding out corruption.

Of course, we’re still going to have it. When I say not much has changed, I am kind of talking about America at large. You’re catching me at a moment, too, when so much is going down across the nation, especially after these last four years.

Boston, yes, actually did get better, so that’s a high point. Boston always gives me hope. I love going there. I love shooting there. It is just so rich. People have been confronting all these issues for so long, I like to think they’re making progress. They’re acknowledging what’s going on. They’re looking at it.

M&C: You are not known as a singer. What is your music background? Were you comfortable singing?

Jill Hennessy: I used to be a busker. I was a street musician for a lot of years in Toronto. Because I played guitar, it was such a great way to earn money. I also played in the street here in New York City.

To be honest, I am much more comfortable with a guitar in my hand playing Tracy Chapman, The Cure, or Bruce Springsteen, but to sing a church song, especially acapella, scared the bejesus out of me because it’s so intimate. For Jenny, too, it’s almost like a whisper or a prayer. That whole song is like a prayer.

M&C: Ben Affleck, Matt Damon, Tom Fontana, Barry Levinson, the show has quite the pedigree. What does having all these big names attached do for the show?

Jill Hennessy: You would have to ask the producers that one. It was sold to me as Michael Cuesta was directing and this incredible writer named Chuck McLean had written the script in this different, fresh, authentic voice. Mainly, they were looking for someone to play Kevin Bacon’s wife.

I was, “Kevin Bacon, please. I would bring him coffee at crafts services.” And Aldis Hodge, who I was a fan of from Underground. So I was, “Jeez, you’ve got to be kidding me. That’s the cast.” I didn’t even know about Ben Affleck and Matt Damon at that point, so that was all icing on the cake. I was down from the get-go.

M&C: Is New York doubling for Boston?

Jill Hennessy: Yeah, in a lot of ways. We have some exterior shots that are from Boston, especially during the shutdown the specific churches we have been using – we actually used them for Seasons 1 and 2 – are in Yonkers.

Boston, itself, has undergone so many renovations since the early 90s that there are a lot of places in Staten Island, Yonkers, and Queens, where you will find more authentic architecture and design that’s closer to 90s Boston than you will in Boston today.

We just shot a lot of scenes in City Island, which I, unfortunately, had never been to, and it’s this beautiful, tiny enclave just north of Manhattan, and, man, the architecture has not changed, since I would venture to say, the 70s. It is incredible and it is a beautiful little artists community and great seafood.

M&C: Any chance you will direct an episode?

Jill Hennessy: Oh, my gosh. That is a great idea. It has crossed my mind, maybe in Season 2 or 3. Maybe in Season 3 possibly.

City on a Hill airs Sunday nights at 10/9c on Showtime.

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