Why Dale From Widow’s Bay Looks So Familiar

Prior to landing a gig at the most haunted island in America, Jeff Hiller appeared in other comedies, horror shows, and even cop dramas. Hiller takes on the role of Dale in Apple TV’s Emmy-winning comedy “Widow’s Bay,” adding some fun bits of humor as the quirky town hall employee.

“Widow’s Bay” viewers who feel they’ve seen Hiller before have probably watched at least one of his guest appearances or recurring roles on TV. Most notably, Hiller won an Emmy in 2025 for his supporting performance as Joel in HBO’s “Somebody Somewhere,” which lasted three seasons. Among Hiller’s biggest shows is the sitcom “30 Rock,” in which he played a hotel employee in Season 3 and a flight attendant named Stewart in Season 5. Elsewhere in the comedy genre, Hiller portrayed the security guard Phil Miller in every episode of “Nightcap” and guest-starred as the ill-tempered coffee shop manager Tim in an episode of “Broad City” Season 4. 

Although best-known for his comedy work, Hiller has dabbled in police procedurals like “Law & Order: Criminal Intent” and “FBI: Most Wanted.” He also has experience in the horror genre, appearing as various characters in “American Horror Story” and its spinoff, “American Horror Stories.” Apple TV audiences should recall Hiller’s scene-stealing performance as Larry in Episode 4 of “Pluribus,” which earned him a 2026 Emmy nomination.

Now that “Widow’s Bay” Season 1 is in the books, fans of the show might be curious about when and where Jeff Hiller will show up next. Apple TV has already green-lit “Widow’s Bay” Season 2, which will start filming at some point in 2027. Hiller will be back as Dale alongside the main cast in the forthcoming batch of episodes, and he has been promoted to a series regular after appearing in Season 1 as a guest actor. 

According to Hiller, Dale was originally meant to die in Season 1 before plans changed. “I was initially just there to be a character who reveals that Richard Warren dying didn’t kill the curse,” Hiller told Decider. “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.'”

Having garnered near-universal praise from TV critics and general audiences, “Widow’s Bay” should offer plenty more laughs and scares in its next season. Perhaps Hiller will make another cameo in “Pluribus” Season 2, but either way, Apple TV subscribers can expect to see him on their screens again.