Halley Feiffer's Deadly Frenemies

As of late, playwright Halley Feiffer has learned to field two types of reactions from friends, family and fans.“Oh my God, that was so funny,” some gush after watching her newest dark comedy, “How To Make Friends and Then Kill Them,” about the horrors of a co-dependent female friendship that is staging through Saturday, December 14, at the Rattlestick Playwrights Theater in Manhattan. “We were laughing so much.”

The rest look at her like they want to jump in front of a train.

Ms. Feiffer deems that a success.

It has not been a smooth road getting there, she explained last week during a telephone interview from her home in Brooklyn. Even with her accomplished list of acting and writing credits, all-American good looks and an abundance of famous connections—most notably her father, East Hampton-based cartoonist Jules Feiffer.

“I think the downside, the challenge with that, is, he made it look easy. And it’s not,” the 29-year-old laughed of her father’s success. “And that’s been a challenge: finding my own way, trying to make a career and a living being an artist. My path is different from his path.”

It began with a young Ms. Feiffer swimming through the city’s acting agent pool with the help of her father. She was 12 when one finally signed her, sending her off on auditions for jobs that she rarely booked.

As much as she loved acting, her heart was elsewhere. She was just too afraid to try.

“For whatever reason, writing scared me more than acting,” Ms. Feiffer said. “I knew I wanted to be a playwright, but it frightened me very much. I didn’t really start committing to it until a couple years ago.”

With a high school playwriting class under her belt—at none other than Rattlestick—Ms. Feiffer left the Manhattan hustle and bustle behind, and headed to Wesleyan University in Middletown, Connecticut. Population 47,325.

She didn’t fit in.

“I felt much more isolated than I was anticipating,” she said. “This is really not the case in my life anymore, but in college, I struggled with intimacy and friendships with other women. At that age, we don’t know how to express ourselves honestly and openly, so we will say cutting or passive-aggressive things, hoping that gets the message across. That never works. I was interested in exploring that broken dynamic.”

In 2007, Ms. Feiffer did. “If It’s Weird Now: Short Plays About Friendship” was her first stab at serious playwriting, she said, but something about it just wasn’t right.

“I kept rewriting it and rewriting it,” she said. “I knew it could be really great—or what I think is really great. And it just wasn’t.”

Years passed. The collection sat dormant and unfinished in her computer, tantalizing Ms. Feiffer every time she revisited it between new writing projects or acting jobs. In 2011, she made her Broadway debut alongside Ben Stiller and East Ender Edie Falco in “The House of Blue Leaves,” earning her a Theatre World Award. A month after the show wrapped, she began filming “He’s Way More Famous Than You”—starring and co-written by Ms. Feiffer, who portrays the worst-imaginable version of herself, that is now available on DVD.

“I play a character called Halley Feiffer, who’s an actress who shot herself in the foot and lost her career because she’s a horrible alcoholic and a narcissist and a diva and delusional and insane and treats everyone terribly,” she said. “But it’s a comedy. The inspiration there was a horrible, dark fantasy about what my life would be like if that were true.”

That combination of dark and bleak with humor and mirth—a perspective also shared by Mr. Feiffer—rings true through most of his daughter’s work, including the full-length play “How To Make Friends and Then Kill Them.”

It was about four years ago that Ms. Feiffer figured it out. The trick was distilling her collection’s 40 female characters into three: a sexy bombshell who is always drunk, an insecure talent who constantly doubts herself, and a “horribly deformed girl who can’t do anything right, but is really nice,” she said.

“I think, in some ways, they’re all me. Or parts of myself,” she said. “But it’s a pretty stylized, surreal play. Anything that is based on anything is taken to a crazy, hyper-stylized level that it stops being based on any particular person. It was like a big lump of clay that, by the end, I’d molded into a beautiful bowl.”

Seven years of rewrites later, Ms. Feiffer was still making last-minute edits up until November 5—two days before opening night; two days before watching her oldest play come to life on stage.

“I’m not married, but it’s what my married friends say about weddings,” she said of the show’s premiere. “‘Was it really the best day of your life?’ And they’re like ...”

She paused and, in a girlish voice a few octaves higher, said, “‘Yes.’”

After a month-long run watching the production from backstage or alongside the audience, Ms. Feiffer remains humble—cognizant of her struggles, her successes and, most importantly, her roots.

“We would literally have class up on that stage and I would sit in those seats. And, now, I’m there again,” she said. “Fourteen years later and I’m there in a different capacity, but also the same capacity. It’s really exciting and moving. Because there’s so many points I could have given up. And I’m glad I didn’t have the persistence to give up.”