‘Loot’ Boss on Casting Henry Winkler as a Billionaire Nudist in Season 3

[Warning: The below contains MAJOR spoilers for Loot Season 3 Episode 1, “Bye-Bye Mode.”]

Loot‘s third season has finally arrived, picking up where Molly’s (Maya Rudolph) story left off. Her attempt to flee California after kissing colleague Arthur (Nat Faxon) went awry. The premiere finds her stranded on an island with assistant Nicholas (Joel Kim Booster), but the marooning is a ruse constructed by him to make Molly believe that they crash-landed.

It turns out that they’re actually on an island where one of Molly’s multimillion-dollar homes is, alongside another billionaire named Gerald (Henry Winkler). When her team comes in search of her to get her to come back home, the illusion for Molly is shattered, and she’s not even that upset that Nicholas lied to her about the crash-landing.

Still sad about Arthur being in a relationship with someone else, she resigns herself to staying on the island, but brokers a deal with Gerald to help get her friends off the island with his ferry.

Apple TV+

The catch? Gerald is a nudist who lives among like-minded senior citizens. “Henry was amazing,” co-creator Matt Hubbard gushes about Winkler’s guest role. “We really wanted to have some other comedic powerhouse on the island in Episode 1, and we were so thankful that he was willing to do it.”

Ultimately, Molly manages to get her friends going on their way, only to be met on the beach by Arthur, who professes his feelings for her. The pair share a sweet kiss, and she decides to return so they can continue their charitable work with her billions. “The beginning of the season is about her contending with that decision and realizing that that’s not the right way through a very absurd series of circumstances,” Hubbard says about Molly’s initial reluctance to break from the island life she’d been living.

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“One reason we put another billionaire in the premiere is because, as this show has gone on, billionaires have become a part of our lives in the real world,” Hubbard explains. By introducing Gerald, the show highlights another way a billionaire is using their money for themself as opposed to what Molly wants to do with her funds.

As Hubbard puts it, “This is really about Molly moving from the defensive to the offensive this season,” and she’s getting bolder in her pursuit to hold other billionaires accountable. Stay tuned to see how that continues to unfold, and let us know what you thought of Loot Season 3’s premiere in the comments below.

Loot, Season 3, Wednesdays, Apple TV+