Meet ‘Cupertino’s Unlikely Duo Taking Down Silicon Valley’s Giants

Elizabeth Fisher / CBS

When we first meet Olivia, she has a choice to make: Return home to her evangelical parents who’ve been itching for an excuse to bring her back, or take a chance on Michael, a relative stranger with big dreams. “Their visit is a nice option, a safety net… but that confluence of Michael coming at this exact moment with this whole other life that’s beckoning her… he opens that door for her,” Keller (Tokyo Vice) says.

Without spoiling the results, let’s say they make an unconventionally excellent team.

Per Colter, that’s because while Michael “stands out in Silicon Valley,” Olivia and her Midwestern manners serve as the “Trojan horse” of the two, “someone who sort of disarms them, or at the very least, distracts them.” For Keller, Olivia’s blend of “chutzpa” and “naivete is crucial” at the start.

The odd professional couple declares an agenda to target the seemingly untouchable — with often humorous results. Robert likens their legal strategy to pulling off a heist. “You really want to win and screw them over in some way and find a loophole in the law to get what you want.” What better target than the grotesquely wealthy and powerful who rule the world with such “smugness”?

Elizabeth Fisher / CBS

It’s not just justice or revenge they’re after, though. Olivia is driven by a desire for money and proving her mettle in a male-dominated industry. “Young women are underestimated,” says Keller. “We see her throw it all out the window and use her instincts and bravery, which gathers and solidifies as the series goes on.” For Michael, it’s about “moving out of the shadow of the father,” a famous entertainment lawyer, along with “feeling like he needs revenge for being wrongfully treated but also discovering that there is some opportunity out there, and in doing so, you’re also doing good,” Colter says. Getting to go toe-to-toe with his ex and former colleague Nichole (Renee Elise Goldsberry) in court, on occasion, is just a bonus.

Rounding out the lead cast is Ella Stiller as the duo’s gum-smacking Gen Z assistant with a gaggle of blue-collar family members and former TGI Fridays’ colleagues at her disposal. “Her more unconventional approach to the job is actually what makes her so good at it,” Stiller says. “She’s got her web of connections, and she’s going to break some rules.” Robert was inspired by his own familial ties in creating the character: “I have a big family of cousins, and they’re all in what you would call brick and mortar jobs, and they all create a spider web of, ‘Scratch my back, I’ll scratch yours,'” he explains. “It felt like a good way to do a secret weapon investigator that you don’t see coming.”

Elizabeth Fisher / CBS

Popping up at opportune (and sometimes inopportune) times is Busy Philipps as Natalia Boutella, the vengeful ex of a billionaire AI mogul who decides to bankroll the new firm. Her persona was at least partly inspired by Kim Kardashian‘s own attempted foray into the world of law. “There is nothing better than writing to an actor who has comic chops,” says Michelle, with Robert adding, “Busy came in and just blew us all away. So I think we’ve been writing more to her than we anticipated.”

TV fans should brace for a cascade of quirky white-collar clashes with zany twists aplenty when Cupertino arrives.

Cupertino, Series Premiere, Thursday, October 8, 10/9c, CBS