Jeff Hiller Secretly Auditioned for Widow's Bay — and Ended Up on the Poster
The Emmy winner discusses Dale's mysterious backstory, scene-stealing moments, and how a small role on the Apple TV hit kept getting bigger.
Since this is, unofficially, a Widow’s Bay — and Jeff Hiller — fan account, the June bonus issue presents an extra-special treat: Jeff Hiller, himself, talking about Widow’s Bay!!
Jeff, who happens to be a Whatever Nevermind subscriber (pardon the flex), joined me to discuss some very fun behind-the-scenes moments behind the buzziest show on TV, his musings on his character Dale’s mysterious backstory, and Gen X career lessons we can take into our own lives. Hope you enjoy the conversation as much as I did — I spent most of our Zoom laughing my face off with delight.
Just a reminder, it’s summer sale — and thank-you — season, so enjoy 50% off annual subscriptions through July 4. I’ll be back next week with a steamy deep dive into another buzzy show of the summer — one with deep 1990s roots and lots of ’80s musical influence.
As always, forgive any stray typos — I’m my own editor — and if you’re reading this in email, the full experience lives in your browser. If you’re feeling generous and if you also don’t have Spotify Premium, please tap the ❤️ at the bottom — it really, really helps!
Warning: Spoilers for the entire season of Widow’s Bay below.
After seeing Jeff Hiller pop up on all my favorite shows this season — Pluribus, Will Trent, Elsbeth, and Ghosts — it was especially wonderful to see him appear, all smiles, on my Zoom screen just before the Widow’s Bay finale, in which he plays Town Hall staffer and erstwhile party DJ Dale.
Of course, we’ve seen Hiller on our faves over the past two decades, from playing computer tech Stan (or Sasha?) on Law & Order: Criminal Intent to Crazy Ex Girlfriend to a couple American Horror Stories. But he really broke out — and won an Emmy — for his role as Joel in the dramedy, Somebody Somewhere. As Sam’s (Bridget Everett) best friend and steadfast supporter, Joel is truly the heart of the three-season series as the pair navigate quintessential Gen X highs and lows: grief, midlife disappointments, long-simmering family resentments, and the joys of found family — and unexpected love. (His acceptance speech — and pink Dear Tyler suit — belong in the pantheon of greatest awards-show moments.)
In Widow’s Bay, his character Dale steals scenes with Hiller’s singular deadpan deliveries, instinctual improv skills, and animated expressions that say 100 words — and deliver 1000 jokes — without making a sound. (Unless he’s screaming, which we do discuss.)
Hiller explains that he auditioned for Dale without first mentioning his tape to the show’s creator and co-writer Katie Dippold, whom he’s known since their early-aughts UCB days. At his manager’s urging, he eventually reached out; Dippold was immediately on board, but warned him that Dale would be a relatively small part.
“I was like, ‘No, I don’t care,’ so she put me in it,” says Hiller. “Then as the season grew, she put me in a little more stuff.”
Dale’s scenes may be brief, but they’re impactful — whether hilariously projecting bewilderment at the usually tightly wound Mayor Tom Loftis (Matthew Rhys), who’s on an accidental hallucinogenic trip, or DJ-ing coworker Patricia’s (Kate O’Flynn) Sunset Cocktails with impeccable taste in ’80s and ’90s party anthems as she unwittingly doses the town’s mean girls and unsuspecting tourists.
In a pivotal sequence in the season finale, Dale — on the hunt for “games and cards” to distract restless vacationers in a storm bunker — wanders into a creepy room and uncovers just how horrifyingly deadly the island really is.
“Then I won an Emmy, and they put me on the poster,” quips Hiller.
Ahead, Hiller discusses why Dale’s a “bad DJ” (it’s not Spotify’s fault), how he almost ruined a take by laughing so hard, and what his secret is to pulling off perfect comedy. And, I got a “touché!”
I listened to Katie on The Hollywood Reporter’s I’m Having an Episode with Mikey O’Connell podcast, and she said she wants to do a Dale episode for season two. So that’s what I’m excited for!
Oh! So maybe I didn’t die.
What type of backstory did you make up for Dale? Was he born on the island? How did he learn to DJ?
He specifically says he has never DJ-ed before. Originally, that role was written for a DJ, who’s really bad at it, that Patricia hires. The director, Samuel Donovan, said, ‘What if Dale did it?’ And then that explains why the DJ is so bad at it, and I thought that was great.
It hasn’t explicitly been stated, but I believe Dale was born on the island. I don’t know how much I’m allowed to say about the lore. He is just living his life, but I do think he has some dark secrets. I believe everybody who was born on the island has some dark secrets. I don’t know exactly what his secrets are, but he is somebody who’s really good at just bifurcating his life and being like, ‘I’m at work now.’ I don’t think he cares very much about work. It’s very much like a check-in, check-out situation.
I feel like Dale and Rosemary (Dale Dickey) have some fun work breaks together.
I think he is locked and loaded every time she has some gossip. He’s ready.
So you do some of the most excellent face acting that I’ve ever seen, like no words, just facial expressions — especially in the season finale when Dale is watching those terrifying instructional films. What was your approach to those perfect expressions, and how do you time them?
Well, they showed me the footage, off camera, and then I went in and pretended to watch it on camera. I was very honest with them. Like, ‘I don’t know how big you want me to go.’ So I gave some subtle ones, some really big ones, and then some medium ones, and I don’t know what they chose. I haven’t seen the episode yet, so I guess my technique is hope for good editing!
No, it’s great. I want to say maybe the middle, because it’s very impactful, but you save the scream for later. About your screaming — one of my favorite moments is in episode five, when Tom is high on shrooms at the Town Hall office, and spontaneously screams — and you immediately scream in reaction. I’ve watched it so many times. How many takes did you do? How did you keep a straight face?
That was one take and the brilliance of director Andrew DeYoung, who just happened to be shooting that. [Rhys] screamed, so I screamed in response. It was just an improv situation, but he caught it in the mirror. It was so perfect.
Tom also hallucinates that Dale has a zombie face, which was subtle but really scary.
People were like, ‘What is that? Is it prosthetics, or did you just not move your mouth?’ It was an actual mask of my head that this guy came and scanned my face with. They used to have to make a caster mold of you, but now they just scan your face. Several of us were supposed to have had that, but the budget made it only one. So that was me.
I saw a BTS picture of you on Katie’s Instagram and the mask is unsettling. (Slide 9 and you’ve been forewarned.)
It is so disturbing, which is so Katie Dippold. I can’t even tell you. Also, when you see your own flesh in front of you, it’s like, ‘Oh my god, I need a facial so bad.”
Katie also said on that podcast that the show is so perfectly funny because the entire cast plays it so straight, which is your skill. Like in Somebody Somewhere, I’m crying one minute, then laughing the next. How do you do that?
Well, that is the key to comedy, isn’t it? Really, it’s just you play it authentically. I think a lot of times people come at comedy in a way that’s like, ‘I’ve got to play the comedy!’ and really it’s about playing the truth, and the comedy shines from it.
You know that old saying — it’s so cliché at this point, but [paraphrasing Aaron Sorkin-written dialogue between Matthew Perry and Sarah Paulson in Studio 60 on the Sunset Strip, but in Patti Lupone-esque voice]: ‘I always get the laugh when I ask for the butter, but why didn’t I get the laugh last night? It’s because you asked for the laugh instead of the butter.’ They’re all asking for the butter, and they’re very, very good at it.
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Matthew Rhys has said that it was so hard for everyone to keep it together while filming, just because you’re all making each other laugh by being so great at your jobs. What’s the most memorable moment of just basically not being able to film a take because you all were laughing so hard at each other?
I wasn’t even in this take, but I was just watching it in video village, and it was the first time I realized, ‘Oh, Kate O’Flynn is amazing.’ In the pilot, Tom says the New York Times is coming to interview him about Widow’s Bay trying to be the next Martha’s Vineyard, and they need to do whatever it takes to impress the writer, and she goes, ‘What are you asking me to do, Tom?’
I was laughing so much, I was like, ‘Oh, I gotta stop, I gotta be quiet, I’m gonna ruin the take.’ I also was like, ‘Oh, now I get the tone of this.’ She really nailed what the tone was.
So what is your relationship with horror?
I really like horror. My sister’s so terrified of horror, like, we saw Us, and she was screaming when young Lupita Nyong’o drops her candy apple in the literal opening scene, like ‘They’re gonna kill that girl!’ I was like, ‘That’s young Lupita Nyong’o. You know she makes it to the next scene.’
Well …
Touché.
I like getting scared. Katie Dippold famously — amongst a very small group of people — throws these parties where we all go see a horror movie on the night that it comes out, and Neil Casey [who plays Breakwater Inn owner Kurt] and [writer/producer] Colton Dunn are always there saying funny things under their breath. I remember we went to see Cabin in the Woods on opening night, and Katie was like, ‘You sit next to me.’ She just wanted to watch me watch the scariness. She loves the laughter of the scare from people. I think that’s why she probably included that scream in episode five because she likes my scream.
This interview has been edited and condensed for clarity.
Behind the paywall, Hiller — whose excellent memoir, Actress of a Certain Age, is delightfully and touchingly Gen X-specific — shares his most Gen X characteristic from growing up in 1980s Texas, how it helped him persevere in his career, and some wisdom for those of us facing our own career pivots.
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