Wealthy Molly Wells (Maya Rudolph) continues battling the billionaires through philanthropy in the third season of Loot
The start of Loot’s third season swiftly tumbles into the absurd, as billionaire Molly Wells (Maya Rudolph) believes she is stranded on a desert island, Gilligan’s Island style, with assistant Nicholas (Joel Kim Booster), when, in fact, this is all an elaborate ruse he’s orchestrated to let Molly shake off the embarrassment of having made a surprise visit to Arthur’s (Nat Faxon) house only to find him with his new girlfriend, Willa (Hayley Magnus). Pretending to be stranded on the grounds of a luxury resort seems extreme, but the gesture sets the scene for the entire season. “I think we learn that Nicholas will literally move mountains to make sure that Molly is protected, comfortable and insulated,” says Booster. “That’s a really nice, sweet impulse, but it’s not always to the betterment of Molly or their relationship.”
If there is such a thing as too much insulation, Molly is not in a place where she cares. “Molly is totally self-absorbed at the beginning of season three. She’s shut down. She’s so humiliated and embarrassed at overstepping in her relationship with Arthur and just wants to run away from everything,” says Rudolph. “She doesn’t even know where that is. She literally leaves it in Nicholas’ hands.” The show’s tone being what it is means that Molly’s pain morphs into broad comedy — not just in the arrival of Molly’s entire team, but in the introduction of another eye-raising group on the island that has guest star Henry Winkler at the helm. “I think the balance of those two extremes is the sweet spot of this show,” says Rudolph. “We’re talking about a rarefied world yet trying to find the humanity and the relationships within that.”
This season is all about exploring kinks in various relationships. First and foremost, what would the real-life challenges be if Molly and Arthur were able to give things a go? “How different their lives are,” answers Rudolph. “You take that big leap with the other person because you genuinely want to be with them, but then the reality of your lifestyles set in. I think they really have to be honest with themselves and each other about if that can work. They’re very different people.”
So different are their worlds that Nicholas isn’t sure if Arthur is up for the task of dating Molly. “I don’t think Nicholas has ever met a boyfriend of Molly’s that he truly thinks is the real deal or worthy of her,” admits Booster. “And then there’s Arthur, who he has very conflicted feelings about because he’s obviously very good friends with him. But I think Nicholas, even before Molly, sees the incompatibilities in their lifestyles. And, unlike Molly, he doesn’t quite understand why she would want to change hers to accommodate him.”
Another relationship that gets rattled this season is that between Sofia (Michaela Jaé Rodriguez) and Howard (Ron Funches), when Sofia’s sister Destiny (X Mayo) arrives in town. “One of the things I really liked [about that storyline] was that, as you become adults, you start to build your own life the way that you want people to view you, but your family knows you since day one,” says Funches. “So Destiny comes in as a person who can pop through Sofia’s bubble of ‘I’m all-knowing, I never get flustered. I’m the one in charge.’ When Destiny comes in, little Fifi [emerges].” Destiny also threatens to come between these two colleagues, as Howard takes a liking to Sofia’s sibling. “Sofia has more information about her sister than Howard does, and she cares a lot about Howard and doesn’t want to see him hurt,” says Rodriguez. “That is the best part about this for me. I love that she cares deeply about Howard.”
Each time they uncover new vulnerabilities in their characters, it is that balance between humour and emotion that the cast continues to love about the zany comedy series. “Some shows are just doing humour, but the characters don’t really grow and change. And then there are shows where the characters are growing and changing, but I wouldn’t necessarily call them comedies,” says Funches. “I think Loot does a great job of threading that needle, and I think it’s because of the writing of people who come from 30 Rock and Parks and Recreation — and just Maya, in general.” As much as ever, the comedy never misses an opportunity to poke fun at billionaires. But what Rudolph also hopes is that the show inspires those with real-life coffers. “There’s a beautiful balance that the show is able to achieve, in terms of trying to find ways to talk about [billionaires] in the reality of the world that we live in and how philanthropy can actually be used in radical ways,” says Rudolph. “It’s exciting that we’re part of that conversation and I hope that it’s rubbing off a little bit. Sometimes we hear that somebody gave a billion dollars away, and I’m like, I wonder if they watch Loot?”
Loot, streaming Wednesday, November 26, on Apple TV