A Knight of the Seven Kingdoms had the Trial of Seven. The Pitt had Robby and Baby Jane Doe. Widow’s Bay has a shaman.
We are now five episodes into the first season of the Apple TV+ horror/comedy series Widow’s Bay, and it’s clear that Apple has its next impeccably written, critically adored comedy show in a long line of thoughtful, genre-bending series from the streamer. Created by MadTV and Parks and Recreation veteran Katie Dippold, Widow’s Bay is the rare hybrid series that never sells out horror for a laugh and never gets too scary to have fun.
Like any comedy series that deserves to be listed among the best shows on TV, Widow’s Bay is a project built on its performances, specifically those of star Matthew Rhys, who plays the titular island’s ambitious, disheveled mayor Tom, and Stephen Root, whose superstitious sailor Wyck serves as Tom’s adversary-turned-ally.
Then, in today’s new episode, “What To Expect On Your Trip,” the alt-comedy icon whom Mike Birbiglia once described as “if the movie Janet Planet were a comedian” made an appearance to give viewers at home a lesson in making every single onscreen moment count. Chris Fleming’s performance as the drug deal– er, “shaman” Todd O’Connor who doses “Wyck” with the most potent hallucinogenic mushrooms on Widow’s Bay isn’t just the best appearance from a guest star in 2026 – it’s the best four minutes of television in 2026.
There is simply nothing more entertaining than watching Chris Fleming pretend to be a cisgender straight man.
Spoilers ahead for any Widow’s Bay fans who haven’t yet watched “What To Expect On Your Trip,” in which Tom, Wyck and Patricia track down Todd after following the leads left by the late Reverend Bryce before his disturbing passing last week. The trio learn from Todd that, shortly before his death, Bryce ingested a species of mushroom called “truesight,” a substance so powerful that even Todd won’t touch it with his ten-foot arms.
Todd will, however, administer it to an unknowing Tom after mistaking him for Wyck, who volunteered to give his third eye Lasik in order to discover the truth about the town’s strange occurrences. Todd then brings Tom to his “peace center” and lays him on the “mindfulness bed” before immediately leaving to deal with his girlfriend’s “absconded” cat.
While Fleming only had a handful of lines during his brief cameo, every single line reading brought a new layer to Todd that elevated him to all-time side-character greatness. And while Fleming may be the best guest star of the series (so far), he’s far from the only actor in Widow’s Bay to prove right the old adage about small roles and small actors.
For instance, The Righteous Gemstones‘ Tim Baltz stole the show in the episode “Lodging” playing Willy, the clean-cut, disarming and ultimately horrifying “guest” at the local inn. Similarly, Dale Dickey has been a scene-stealer in her role as Rosemary, the endlessly nonchalant and unreasonably supportive glue girl of the mayor’s office. And, of course, Kate O’Flynn can’t help but bring heart and cringe to every moment that Patricia is involved in the action.
Really, there hasn’t been a single role on Widow’s Bay that wasn’t knocked out of the park. Every character is hilarious, peculiar and charming all at once, and every actor makes an impression with whatever screen time they’re allotted.
But, as of tonight, Fleming holds the spot for most memorable side character in the series, although we’re not going to hold our breath for a repeat performance – on this island, creatures that abscond rarely reappear.
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