'Kidding' showrunner on Ariana Grande and the power of healing

Fans of Showtime's Kidding are used to having our imaginations stretched, but Season 2, episode 5 pulled off a whole new fantasy. We spend the entire time inside an episode of Mr. Pickles' Puppet Time, complete with musical numbers, emotionally volatile puppets, and the fairy of hope (in flats!): Piccola Grande (Ariana Grande).

With Piccola's help, the puppets of Pickle Barrel Falls prepare to say goodbye, and Mr. Pickles himself (Jim Carrey) gets ready to sign divorce papers, surrendering the dregs of his marriage to the incontrovertible reality that set in after his son's death.

"There were a lot of wrong ways to write this TV show," showrunner Dave Holstein tells Mashable in a phone interview. "One of those ways would’ve been just to sit back and watch somebody spiral into madness. For me, it was about starting a show in darkness and walking it closer and closer to the light every year."

Kidding has always deployed magic tricks to drive its emotional punches, and episode 5 is one of its finest in that regard.

"It’s a lot to ask an adult audience to sit through a half-hour children’s show," he says. "I felt to be able to keep the audience’s attention we had to throw everything we could at it, including musical numbers, including celebrity guests, whatever we needed to do."

But Grande's involvement is no novelty act, Holstein says. The international pop star counts herself among Carrey's and the show's fans, and with that and Holstein's musical theater background, the episode fell into place.

"She just has this crushing emotional voice, which fit our show so well," he says. "Her voice, especially in the right context, really accesses that part behind your eyes that decides whether or not you cry. We wanted to take full advantage of that, especially to emphasize the beauty in Jeff’s world."

Jim Carrey as Jeff Pickles, Ariana Grande as Piccola Grande and Catherine Keener as Deirdre in 'Kidding.' Credit: Beth Corey Dubber/SHOWTIME

Piccola helps Jeff and his many departing puppets say goodbye, then finally gather in support for him as he signs the papers alongside soon-to-be-ex-wife Jill (Judy Greer). Grande only appears in this episode, but that voice will return before the season ends — along with another unexpected popular artist doing a special cover for the show: Ke$ha.

"There’s some thematic cohesion in taking a lot of these pop stars and asking them to be more raw and sort of tear away their own artifice and be vulnerable with our viewers, which I think is something very special," Holstein says. This is the same season that he inconspicuously slips in cameos from Tyler the Creator and Blake Griffin (that last one being less sleight of hand and more "just a nice guy that plays basketball well").

It's worth noting that both Grande and Ke$ha are no strangers to loss, trauma, and healing, and that their journeys from darkness toward light have played out on an excruciatingly public stage. Holstein recalls discussing that deeply with Grande as she recorded her songs for the episode.

"She has to get on stage every day and sing these pop songs that are about her breakups, and about her most traumatic events in her life, and she has to do that every single day in front of cheering fans and the toll that that takes... but that’s also how art is made," he says. "We alchemize our pain into entertainment."

Kidding airs Sundays at 10 p.m. ET on Showtime.