character study

How Kelli Prenny Went From Insecure’s ‘Eye-Roll Friend’ to Zany Voice of Reason

Photo-Illustration: Vulture. Photos: HBO

The Character: Kelli Prenny, the fourth corner of Issa Dee’s close college friend group. Always prepared with a clever quip or comeback, Kelli was originally introduced as the “party friend”; in the final season, she’s California sober (minus Champagne, which “ain’t alcohol”), on a path to enlightenment, and intent on becoming BFFs with all her friends’ moms.

The Actor: Natasha Rothwell, 41, a longtime improv performer and comedy writer whose résumé 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 show’s first season.

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

The ‘Eye-Roll Friend’

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 HBO’s 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 didn’t 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 Issa’s world with real people aside from Molly and Lawrence, Issa’s 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 Kelli’s 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, you’re 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.

Casting Natasha Rothwell

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; Kelli’s antics are positioned as funny party stories and she employs her signature comedic timing to rag on her friends, from “awkward bitch” Issa’s attempt at open-mic rapping to Tiffany’s “flawless-ass face.” But even in these somewhat broader, cliché character lines, Kelli immediately shows a thoughtful, more feminist side when she holds court about the type of man she’s looking for. Kelli is sexually free and won’t compromise when it comes to dating; from her first scenes, she’s 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 season’s 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, “she’d 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 production’s 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 wasn’t suspicious or even excited about the prospects. I had pretty serious blinders on,” Rothwell recalls. It wasn’t until Rae and Penny asked her to play the part three months later that she realized the character was hers.

Rothwell wasn’t 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 … wasn’t one-note, exactly, but served a specific function. When Natasha was cast, she took the character to entirely different levels,” Dougan says, noting that Kelli’s distinct voice became fully formed with Rothwell’s 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 Kelli’s is “more porous” than Rothwell’s. 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 character’s. In one season, someone pitched a scene in which Kelli would have a nip slip, which wasn’t something Rothwell felt comfortable doing on camera. “I was like, ‘I think that’s 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 [everyone’s] 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, It’s too good not to do.”

Meme Queen

It’s 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, it’s really easy to improvise from their point of view,” she says. “You’re just reacting to the world around you like they would. It doesn’t require a lot of exposition, and you’re not forcing a joke. You’re just responding organically and honestly.”

In the season-one finale “Broken As Fuck,” the four girls go to Malibu for Kelli’s birthday, but tensions simmer in the group. After an awkward drive and an uncomfortable decision about the weekend’s 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 didn’t cut. Issa started that improv run by saying ‘Do you hear yourself?’ That was unscripted. So I was like, What’s the most Kelli response possible? ‘Of course, I’ve 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 Prenny’s 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 Issa’s hope for a reunion with Lawrence. After Kelli accidentally breaks the news that he’s dating someone else, Issa insists she doesn’t 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.

Finding Her Depth

A comedy with its fair share of drama, Insecure needed a character like Kelli to cut through tense moments. Her antics (and Rothwell’s 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 Issa’s block party, Kelli is the character whom fans are constantly clamoring around for a spinoff. She also has an ongoing, inexplicable beef with Issa’s 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: “She’s used for comic relief, but there are things she says that have meaning.” Infusing her with depth was critical. “I didn’t want her to be the butt of a joke,” Rothwell says. “I never wanted her to be hypersexualized. I didn’t want to fall into clichés or stereotypes.”

In Rothwell’s 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 it’s 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. “It’s 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. It’s a moment of character building that shows Kelli’s life is more put together than what Molly and Issa perceive: She’s not only drinking heavily and trying to get laid, she’s out here training for a marathon and striving towards personal goals when she’s offscreen. “That’s 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 didn’t achieve, and she was disappointed. We didn’t go all the way, and it was more satisfying as a result.”

The final season has seen substantive growth for all characters, including Kelli’s own journey toward enlightenment. She’s 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 Kelli’s world as they would have liked, Rothwell thinks that means she’s done her job. “I take it as a compliment that I’ve created someone who’s interesting, and who’s full and rich enough that [viewers] know there’s more to her.”

How Kelli Went From ‘Eye-Roll Friend’ to Voice of Reason