‘Hacks’ Guest Stars Cherry Jones & Leslie Bibb Break Down Deborah and Ava’s ‘Montecito’ Retreat

Hacks delivered some major fan service in the show’s latest installment which saw Deborah (Jean Smart) and Ava (Hannah Einbinder) attempt to win the good favor of a fellow comedian by posing as a lesbian couple.

In the episode, “Montecito,” Deborah catches up with her psychic as she orchestrates her MSG gig, and was told she would be wearing white for the event. Deborah surmised this meant a suit set previously worn by Carol Burnett. The catch? Fellow comedian Kelly Kilpatrick (Cherry Jones) was in possession of the outfit, and she has a long-running beef with Deborah for making jokes about her being a lesbian.

Eager to talk her way into acquiring the outfit, Deborah sets up a lunch with Kelly to clear the air, and learns how much her jokes impacted Kelly. As their lunch meeting was coming to a close, Ava approached the table and Kelly made the assumption that she was more than just Deborah’s writer, but instead her lover.

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While Ava doesn’t overhear this exchange with Kelly, Deborah plays into it and scores them an invite to Kelly’s home in Montecito where they’ll stay with her and her wife, Monica (Leslie Bibb), where hilarity ensues.

Things are immediately complicated when Ava strikes up a connection with Monica, with whom she can’t indulge because of the faux relationship with Deborah… all for the Carol Burnett outfit.

Ultimately, Kelly and Monica learn the truth, but still are unbelieving that Deborah and Ava aren’t a couple, especially after a poolside kiss. Still, Kelly allows Deborah to take the outfit and admits she’s rooting for Ava and Deborah to make it.

When it came to boarding the award-winning comedy for this hilarious installment, Jones admits, “I said no twice because I’d had a major rotator cuff surgery.”

Ultimately, Jones reveals, “I had a meeting with [Paul W. Downs, Lucia Aniello, and Jen Statsky], and I loved them, but I just kept turning it down… Finally, after I turned it down the last time they called again, they just made it so I couldn’t say no anymore. When someone is that persistent, you just love them,” Jones shares.

“Part of it, too, was that I really have had a professional crush on Jean Smart much of my life, and I think of her as a professional big sister even though I didn’t know her from Adam. There are just people you look up to, and so I think my hesitancy was also because I was shy, because I haven’t gotten to do comedy much in my life, so it was just heaven.”

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Meanwhile, Jones’s onscreen wife was equally smitten as Bibb says “[Paul] was like, ‘you’re gonna be with Cherry Jones,’ and I was like, ‘where do I sign?’”

It was a bit of a fish out of water situation for Jones though, who admits, “I don’t watch much television to tell you the truth… I watched the second half of the last season, and I was blown away. It was incredible, I went to such dark places which I loved.”

Still, it was a fun run for the duo, as Bibb recalls Ava and Deborah’s intimate moment, “When they kissed, it was so funny. It was just so great to watch their dynamic in that moment.”

“It’s also so interesting to realize, in a way, Ava and Deborah Vance are soulmates,” Bibb adds, despite the duo’s platonic nature. “I think that they really think they’re gonna help this couple, and that’s what makes it funny, is that they really do think they’re like Doctor Freud and Carl Jung.”

Hacks, Season 5, Thursdays, 9/8c, HBO Max