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Photo-Illustration: Vulture. Photos: HBO

The Character: Kelli Prenny, the fourth corner of Issa Dees close college friend group. Always prepared with a clever quip or comeback, Kelli was originally introduced as the party friend; in the final season, shes California sober (minus Champagne, which aint alcohol), on a path to enlightenment, and intent onbecoming BFFs with all her friends moms.

The Actor: Natasha Rothwell, 41, a longtime improv performer and comedy writer whose rsum includes a stint on SNL. She was the first writer hired on Insecure and was later cast as Kelli after a table read during the shows first season.

Essential Traits: Unfiltered, off-the-cuff one-liners; a ride-or-die mentality for her friends (keeping it real when theyre out of line but going to bat in front of enemies); an inexplicable beef with Issas brother, Ahmal; the life of the party, whether shes drinking and flirting or stoned at her goddaughters birthday celebration.

When Insecure was pitched and picked up by HBO, it was a show focused on best friends Issa and Molly navigating life and love in Los Angeles. Fresh off writing for SNL, Rothwell took a meeting with HBOs comedy chief Amy Gravitt, who identified Rothwell as a good fit for the room. Rothwell then spoke with creator and star Issa Rae and showrunner Prentice Penny. I didnt know if I was gonna get it, but I knew I loved talking to both of them and their thoughts about this world they were gonna create, Rothwell remembers. She was the first writer hired for the writers room, before Kelli was even the seed of an idea.

Once the room was assembled, writer Ben Dougan helped formulate the origins of Kelli Prenny. There was a need to fill Issas world with real people aside from Molly and Lawrence, Issas longtime boyfriend, and Dougan pitched Kelli as the eye-roll friend: a truth-teller who says what she thinks and thinks what she says. Initially, eye-roll friend was supposed to be judgmental, which ultimately became a version of Tiffany, says Dougan. Then we started using the phrase eye-roll friend in a different way: like the friend you roll your eyes at.

Establishing Kellis voice was crucial to understanding the character and her function within the larger story. Dougan recalls a few lines of dialogue from a now-scrapped dinner-party episode in the first season that helped solidify who Kelli was. In the episode, Issa and Lawrence decide to throw a party to prove that they are adults. They get a new couch and attempt to repaint the walls, but in true Issa fashion, she only has time to paint one wall. She tries to pass it off as an accent wall, but Kelli sees through her bullshit and was scripted to call her on it: What happened, you run out of paint? When Issa asks everyone to take their shoes off upon arrival, Kelli retorts: Oh, youre a shoes-off bitch now? The writers room recognized that Kelli could be the straight-shooting friend to push buttons. Not in a mean way, but in a loving way that only a friend could, says Dougan.

Rothwell on set in season four: When Natasha was cast, she took the character to entirely different levels, says Insecure writer Ben Dougan. Photo: Merie Weismiller Wallace - SMPSP/Merie Weismiller Wallace - SMPSP

When Kelli arrives onscreen in the third episode of the first season, Racist As Fuck, she is clearly filling the role of the funny friend who is boy-crazy and looking to take advantage of the open bar. Rothwell brings a confident, warm energy to the role; Kellis antics are positioned as funny party stories and she employs her signature comedic timing to rag on her friends, from awkward bitch Issas attempt at open-mic rapping to Tiffanys flawless-ass face. But even in these somewhat broader, clich character lines, Kelli immediately shows a thoughtful, more feminist side when she holds court about the type of man shes looking for. Kelli is sexually free and wont compromise when it comes to dating; from her first scenes, shes the confident friend who will speak her mind no matter the circumstances or outcome.

Rothwell never had aspirations to join the cast. Though she is a seasoned performer and never hid that part of herself, she was focused on bringing her best writing to the show, as it was her first scripted series writers room. So she pitched jokes and focused on crafting the seasons arc, while often doing bits that showed off her comedic timing and improv skills. She loved to perform in the room as much as she loved to pitch jokes for the show, Dougan remembers. Rothwell would use the office phone to place fake calls whenever a joke she pitched landed or bombed; when it bombed, shed take the phone and turn away from the rest of us, and pretended to field a call from her agent saying she just got fired. It was hilarious.

Rothwell read for the part of Kelli during the productions first table reads, bringing the spunk and perfectly timed line delivery needed for the role. Even though writers in the room often read for different parts, somehow, Kelli always belonged to Rothwell. I started reading for Kelli in every episode she appeared in. I wasnt suspicious or even excited about the prospects. I had pretty serious blinders on, Rothwell recalls. It wasnt until Rae and Penny asked her to play the part three months later that she realized the character was hers.

Rothwell wasnt scared to take the role, but she was nervous it might pull her away from the writers room. I was relieved when I knew I was going to be able to do both and felt supported, she says. Rothwell not only managed both, but thrived while pulling double-duty. The character we were initially brainstorming wasnt one-note, exactly, but served a specific function. When Natasha was cast, she took the character to entirely different levels, Dougan says, noting that Kellis distinct voice became fully formed with Rothwells performance and ad-libs. She took the ball and ran with it.

Once cast, Rothwell says she put all of herself into Kelli, though their personalities manifest in very different ways. Both have filters, but Kellis is more porous than Rothwells. Both are loyal, unapologetic, and opinionated, but the degrees to which those qualities come to the surface are varied, and Rothwell found it rewarding as a performer to calibrate parts of herself that made Kelli feel real. The Venn diagram of Rothwell and Kelli has many overlapping portions some obvious, some subtle which ultimately led to a more nuanced portrayal of the character.

Still, Rothwell had to establish her actor boundaries separate from the characters. In one season, someone pitched a scene in which Kelli would have a nip slip, which wasnt something Rothwell felt comfortable doing on camera. I was like, I think thats great for the character, but the actress is not gonna do it. I spoke with her, Rothwell remembers joking. However, set pieces occasionally made it into the script without her express approval. When Kelli gets fingered under the table at the diner in season-two episode Hella L.A., Rothwell had been in another room working on a different episode. When we went back to read each others scripts at the end of the day, I remember [everyones] eyes on me as we were doing the table read. When we got to the page that it happened, they just started laughing. I was like, Its too good not to do.

Its no secret that improv was encouraged on the Insecure set, and Rothwell improvised for every episode she appeared in. When you understand the psychology of a character, its really easy to improvise from their point of view, she says. Youre just reacting to the world around you like they would. It doesnt require a lot of exposition, and youre not forcing a joke. Youre just responding organically and honestly.

In the season-one finale Broken As Fuck, the four girls go to Malibu for Kellis birthday, but tensions simmer in the group. After an awkward drive and an uncomfortable decision about the weekends sleeping arrangements, Issa snaps at Kelli about her inability to shut up. Do you hear yourself? Issa asks. Kelli retorts, Of course I do, I have a podcast. That was a Rothwell improvisation: The scene actually ends on the page a couple of lines before, but the director didnt cut. Issa started that improv run by saying Do you hear yourself? That was unscripted. So I was like, Whats the most Kelli response possible? Of course, Ive got a podcast. I thought it was just a throwaway. I had no idea it would actually make the episode. Years later, fans were delighted when the podcast Prennys Preguntas got its own scene in the season-five premiere.

Season two made Kelli into a meme. When the gang attends an art exhibit in Hella Questions, the conversation turns to Issas hope for a reunion with Lawrence. After Kelli accidentally breaks the news that hes dating someone else, Issa insists she doesnt want any details about this other woman. Supportive, Kelli remarks, You know what that is? Growth, with a hand gesture that resembles a flower blossoming. A natural hand-talker, Rothwell included the movement in the first and second takes, dropping it for the third in order to provide some variety for the editing room. But director Penny, sensing a winning bit, encouraged Rothwell to follow her instincts after the third take.

A comedy with its fair share of drama, Insecure needed a character like Kelli to cut through tense moments. Her antics (and Rothwells line readings) offer some of the most quotable, laugh-out-loud moments in the show; from getting Tased and peeing her pants at Coachella to adopting a British accent to impress a boy at Issas block party, Kelli is the character whom fans are constantly clamoring around for a spinoff. She also has an ongoing, inexplicable beef with Issas brother, Ahmal, which Rothwell believes stems from an unrequited crush before Ahmal officially came out (Hell hath no fury like a Kelli scorned).

But Rothwell and the other writers wanted to make sure Kelli was more than just the wisecrack. In his notes, Dougan has a quote written down from the early days of her conception: Shes used for comic relief, but there are things she says that have meaning. Infusing her with depth was critical. I didnt want her to be the butt of a joke, Rothwell says. I never wanted her to be hypersexualized. I didnt want to fall into clichs or stereotypes.

In Rothwells hands, Kelli contains multitudes: She is unapologetic and irreverent, she has no filter and is self-possessed. But at the end of the day, she is deeply kind and caring, she says. Kelli is there for Issa when her friendship with Molly is crumbling, nudging Issa to reach out and make amends, even though its the last thing she wants to do. In the season-five premiere, she offers advice to Molly about how to restore their rapport, citing rough patches in her friendship with Tiffany that they worked through.

For Dougan, striking this balance was one of the harder parts of writing for the character. Its easy to take things too far. The biggest challenge was pulling back and remembering that Kelli is a real person. In the season-two finale, Kelli tries to run a marathon but has to stop midway when she gets her period. Its a moment of character building that shows Kellis life is more put together than what Molly and Issa perceive: Shes not only drinking heavily and trying to get laid, shes out here training for a marathon and striving towards personal goals when shes offscreen. Thats a situation where we had jokes that were all blood-related, like calling it the Red Wedding, Dougan says. But at the end of the day, it was a real moment where Kelli had a goal she had been working toward and didnt achieve, and she was disappointed. We didnt go all the way, and it was more satisfying as a result.

The final season has seen substantive growth for all characters, including Kellis own journey toward enlightenment. Shes abstaining from alcohol, asking herself (and her podcast listeners) deeper questions about life, and searching for her true happiness. For a season that tried to answer questions like What do you want your legacy to be? and Am I happy?, Preguntas was a good framing device, Rothwell says. I was super excited to have Kelli shepherd us into that idea for the last season.

Even though fans never saw as much of Kellis world as they would have liked, Rothwell thinks that means shes done her job. I take it as a compliment that Ive created someone whos interesting, and whos full and rich enough that [viewers] know theres more to her.

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Originally posted here:
How Kelli Prenny Went From Insecures Eye-Roll Friend to Zany Voice of Reason - Vulture