Dale, the scene-stealing town hall staffer who quickly became a favorite among Widow’s Bay viewers, was originally headed for a much shorter stay on Apple TV’s acclaimed horror comedy.
Creator Katie Dippold initially brought in her longtime friend Jeff Hiller for what was meant to be a small part — and she made it clear from the start that Dale was not expected to survive Season 1. But once Hiller got on set, the plan changed. His easy chemistry with the ensemble, gift for turning throwaway lines into big laughs, and infectious presence convinced Dippold to rewrite the character’s fate. Dale lived, and Hiller was later promoted to series regular for Season 2.
“I was initially just there to be a character who reveals that Richard Warren dying didn’t kill the curse. I was just supposed to be in the background. I didn’t really matter,” Hiller told DECIDER over Zoom. “And then in Episode 4, there was supposed to be a bad DJ there who ruined Patricia’s party, and Sam Donovan, who directed that episode, was like, ‘What if it was Dale? And that’s why he’s bad…’”
Hiller opened up about Dale’s unexpected evolution while speaking with DECIDER about his guest role on Pluribus, which earned him his second Emmy nomination. The conversation also turned to Widow’s Bay and its impressive awards showing: 19 Emmy nominations in total, including eight early wins, a nod for Outstanding Comedy Series, and acting recognition for Matthew Rhys, Kate O’Flynn, Stephen Root, and Dale Dickey.
“Right now it’s so rare that people will do anything that’s not an IP. And it’s cool that I’m on these two completely new shows, not IP stuff, and that people are excited about them,” Hiller reflected.
Read the rest of our Widow’s Bay conversation below to hear Hiller dish on some of his greatest Dale improv moments, the beloved standout episode “Beach Reads,” his viral finale line, his hopes for Season 2, and more.
You were nominated for your iconic guest role in Pluribus, but you’re also in Widow’s Bay, which received an incredible 19 Emmy nominations. The show has been such a word-of-mouth sensation. Was there a moment where you remember thinking, “Oh, this is a hit!”
Honestly, not the first time I thought it, but the first time I said it — we were at the Hollywood Forever Cemetery. There was this huge crowd with all these people, and Stephen Root goes, “Man, people are excited.” And I was like, “We’re in a hit!”
The cemetery convincing you instead of the 19 Emmy nominations is so Widow’s Bay. Your friend and Widow’s Bay showrunner Katie Dippold thankfully promised we’ll see more of Dale than ever in Season 2. What’s your dream storyline for him?
I think it would just be fun to reveal what it’s like on this island every day. If Tom is driving down the street and meets a sea hag, what happens when Dale gets coffee at the Salty Whale or whatever? I think Dale is definitely not like Joel [from Somebody Somewhere]. At home, [Joel would] have all sorts of live, laugh, love signs and joyous things like that. And I think Dale is like, “Oh, I didn’t know about art. I don’t have any.” But I do think it’d be fun to have some really gross dark secret in the basement, like a twin that he’s hiding down there.
Yes! Oh my god, yes, the Whatever Happened to Baby Jane? pitch. And then you get to play a twin.
Oh yeah! I would be the twin!
Two of your main scene partners, Dale Dickey and Kate O’Flynn, received their first Emmy nominations for Widow’s Bay this year. What was it like collaborating with them?
Well, Dale Dickey, I’ve been a fan of forever. She used to do these Del Shores movies back in the day. And she played Patty, the daytime hooker, in My Name Is Earl. I remember I geeked out because she was in this movie called A Love Song, where she was so good. And Winter’s Bone and Breaking Bad! So I was so excited to work with her, and she didn’t disappoint. She’s so great, and so down, and just in the pocket. But I didn’t know Kate at all. That scene in the pilot when Tom says, “We gotta impress this New York Times person,” and she goes, “What are you asking me to do?” I was watching from the monitors and started laughing so hard because she was so serious and so funny. Kate is also just a great person. You know she’s British, and Matthew is Welsh, so Matthew will be like, “Should we go and run these lawns a bit?” And then Kate will be, “That would be actually wonderful, thank you.” The best British thing she’s ever said was, “Oh, that’s right. Your show’s on HB-ho.” [Laughs]
She and Patricia are both icons. Naturally, I have to ask about the party of the year, Sunset Cocktails. Take me back to shooting that standout episode. What were the most memorable moments for you?
I do remember sitting in the holding area, and we were just running through the scene — it was right before the scene where Patricia realizes she’s wearing the headdress — and some sort of bell ringing. I was like, “That is so crazy. Why do you think Rosemary didn’t say anything?” And Dale goes, “I said I had my qualms.” It was really, really hilarious. I was like, “Oh my God, that is so funny.”
And the Sunset Cocktails karaoke was the most fun. That was all scripted. I didn’t improvise any of that, but the fact that Dale doesn’t have premium… [Laughs] And I loved the dancing. I mean, I cannot say enough about Kate O’Flynn. If you look at the scene when everybody’s supposed to be dancing, you’ll see her, and she’s going crazy. And you’ll see that some of the background folks are just a mess. Cause we had been doing it for so long. But every single time Kate did it, her energy was contagious. And I was trying to dance like Dale would dance. It was really a very fun episode and scene.
I was so locked in on her dancing the first time I watched the screener that I didn’t even notice the jaws drop the first time. I saw them in the mirror, but when I rewatched the dance circle scene again and caught it, I was like, “Wow. I was just looking at Kate.”
That scene is so creepy, and I have to tell you, they told me that I had a very good open mouth. And you don’t even see it in the dancing scene! But we saw it in the water.
I was really stressed out by the open mouths. I was like, “I hope they don’t have TMJ.”
[Laughs] There was this one poor person. She was like, “I am opening my mouth!” She just had a very small mouth.
Another fan-favorite performance of yours is Episode 5 when Tom is tripping on shrooms. What can you tell me about those creepy facial prosthetics and somehow playing it straight opposite Matthew Rhys’ hilarious performance?
Where I scream and stuff — that wasn’t scripted. He screamed, and then I screamed, and it was really that shrill in real life. It was so fun for me, and he was having so much fun with it too. There was even more on the cutting room floor of him just doing weird things that were so hilarious. And then the mask — it’s harrowing to see your flesh in front of you and see all of the blemishes, and freckles, and things. I was like, “Oh, I need a laser.” But you know what? It opened my phone!
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[Laughs] No way, that’s crazy. That mask is like an omen for Dale’s twin in the basement.
Oh my god, right. We’ll just get a dummy and put that thing on it.
I know you and Katie have such strong improv backgrounds, so was there a favorite improv this season that made the final cut?
You know, the one that I am kind of proud of that literally no one has mentioned to me? People talk about the “Oh, no, Rosemary!” line when the painting falls. And they were like, “Yes, you can do that one.” But the one that I thought was really funny that nobody ever mentions is when Tom is at the inaugural swim, and he’s talking. I was like, “I can hear you with that,” when in truth, I couldn’t hear him in real life. [Laughs]
That whole scene was incredible. I know you and Katie revealed that Dale was supposed to die, and I think I heard you say he wasn’t originally going to be in Episode 4, so does that mean you were getting killed earlier? Was the sea hag taking Dale out?
[Laughs] I do know how I was supposed to go out, but Katie has been very firm that I’m not supposed to say it, because she might use it in another episode, which is a very funny episode. I wasn’t supposed to get killed by the sea hag; I’ll tell you that. Although that’s so funny if gay Jeff was getting smothered. I’d flip her off even without scaring. I was initially just there to be a character who reveals that Richard Warren dying didn’t kill the curse. But I won’t say how I died. It was just supposed to be in the background. I didn’t really matter. And then in Episode 4, there was supposed to be a bad DJ there who ruined Patricia’s party, and Sam Donovan, who directed that episode, was like, “What if it was Dale? And that’s why he’s bad.” And I was like, “You guys, I love that.”
Thank you, Sam! I can’t imagine this show without you. I know the incredible finale wasn’t eligible for Emmy consideration this year, but it did give us one of the show’s most iconic lines: “This place is a death trap! Run!” Were you aware of how powerful that would be in the moment, and have you seen it blow up online? It’s a bit concerning how spot-on it is as a reaction to our real-world horrors.
[Laughs] Well, yes. I am concerned. When we were shooting it, I was thinking, “You know, maybe I’ll get a bit of a bigger part.” I’m an actor. But I definitely wasn’t thinking, “This’ll probably get Emmy nominations!” That was before I was even nominated for Somebody Somewhere, so the Emmy thing wasn’t in my mind at all. But after I shouted, all of the background folks and the crew and everyone laughed and clapped. And I was like, “Maybe it was funny!”
Since you were nominated for an Outstanding Guest Actor In A Drama Series for your role as Larry in Pluribus, what’s more terrifying to you: living on a cursed island or the Pluribus hive mind situation?
Nobody’s asked me that yet. That’s such a good question. I think [I’d] probably [prefer] the hive mind. Because the reason Katie loves taking me to haunted houses and horror movies is I scream so much all the time, and I’m just so scared. We’ve gone to Universal Horror Nights for many, many years, and I always need a week to recover. [Laughs] There’s just like a ringing in my ears afterwards from the stress of it. So I think being on the island, I would have a heart attack by the time I was 26, whereas in the Hive Mind, I’d be like, “Eh, just take me. Let’s go.” [Laughs]
Since you’re on such an Apple TV hot streak, is there another series from the streamer you’d love to join next?
Oh my god, they have so many. I love Severance. I really love Severance. And I love The Studio. And I love [Maximum Pleasure Guaranteed] with Tatiana Maslany. That one’s so weird. But I would be on anything.
Widow’s Bay/Severance director Sam Donovan can hook you up. The Severance potential is endless. For all we know, you could be the person Irving’s on the phone with who we haven’t seen yet.
[Laughs] I’ll be the DJ to make Tramell Tillman dance.
You absolutely need to act opposite Tramell in this lifetime. In Somebody Somewhere, Joel was big on vision boards. At this point in your career, if you made a vision board, are there any roles, genres, or collaborators you’d put on it?
Here’s a weird one: I’d like to work with Annie Potts.
Oh, we’re getting you on Best Medicine!
I did audition for Best Medicine! And they gave it to Stephen Spinella, just because he’s a Tony-winning actor!
Oh my gosh! Let’s call Josh Segarra and get you on as a guest to work with Annie. We’re manifesting!
Oh my gosh, I love him too. He’s so sweet. I just love Annie Potts, and I love her career. She and David Hyde Pierce are two people that I’m always like, “I’d like to have careers like them, where they just play off of these different, weird things.” They go to the theater, they go to film, they go to TV. I think it’s just so cool.
Before we wrap, any final thoughts on Widow’s Bay or Pluribus you’d like to share?
I just feel so excited that the world gets to see the truth inside Katie Dippold. It’s her personhood on the page. And I feel like it’s so rare that people can do that. And I feel like Vince does that. He takes this truth of himself and puts it on the page. I’m not saying that he dealt meth or whatever. [Laughs] But I think it’s so cool that Apple allows these creators to do that. I have such respect for both of them, and for Apple, too. Right now it’s so rare that people will do anything that’s not an IP. And it’s cool that I’m on these two completely new shows, not IP stuff, and that people are excited about them.
This interview was edited for length and clarity.
Widow’s Bay is now streaming on Apple TV.