Life of Kiley

“Conan” writer to headline Playhouse 395 fundraiser

“My 16-year old daughter is now taking drama. What could they possibly teach a 16-year old girl about drama that she doesn’t already know?”

“I don’t have the heart to tell my mother-in-law that Movember is over.”

“My kids aren’t old enough to drink and apparently, neither is my uncle.”

“My wife’s drawing classes are really paying off. She just drew a perfect chalk outline of my body.”

The above tweets recently appeared on the  comic Brian Kiley’s website. A staff writer for Conan O’Brien since 1994 and a standup comic since his college days, Kiley will be performing at Playhouse 395’s annual fundraiser on January 25.

The event will take place at the Tri-County Fairgrounds. For details, see the opposite page.

Kiley has appeared on the David Letterman show six times and won an Emmy award for his writing in 2007.

When The Sheet spoke with Kiley this week, he acknowledged that a lot of his humor is drawn from his family.

“Sometimes, I feel a little guilty about the jokes … but usually they’re okay with it. If they were true things, it would be one thing, but … like that joke about my daughter. My son is more drama than she is.”

“My kids aren’t old enough to drink and apparently, neither is my uncle.” – Brian Kiley

Kiley grew up in Newton, Massachusetts, a suburb of Boston, and attended Boston College, graduating in 1983. He says he began doing standup during his senior year.

Post-college, he went into standup full-time, doing shows all over the country, figuring out what worked and what didn’t.

Having just finished Malcolm Gladwell’s book, “Outliers,” Kiley identified with Gladwell’s chapter on the “10,000-hour rule,” derived from research by Anders Ericsson.

In short, if you want to be an expert at something, spend 20 hours a week on it for ten years and you just might get there.

And that’s just about what Kiley did before fellow comic Louis C.K., who was on Conan’s writing staff at the time, suggested he apply for a job.

So Kiley submitted about fifty jokes culled from his standup routine and got the gig. He’s been with Conan ever since.

“We have similar sensibilities,” Kiley says of O’Brien. “We’re both from big, repressed Irish Catholic families … I didn’t have a lot of trouble getting his comedic voice.”

For Conan, Kiley writes about 35 to 40 jokes every day. Of those, Conan might choose 2 or 3 for that night’s monologue.

“Sometimes, he’ll use a joke as a jumping-off point,” explains Kiley.

Kiley then related a story about how he’d written a joke about Charles Manson being busted in prison for having a cellphone.

Conan then went into a whole riff about whom Manson might be speaking to.

Kiley says his standup act is forever a work-in-progress, and that he incorporates new jokes into every performance.

“I usually try one or two new jokes every show,” he says, even though “most of the new ones won’t work – even if you think it’s absolutely gonna kill.”

He then referenced Jerry Seinfeld, who believes that about 10% of what he writes works.

“You don’t want to do stuff that’s gonna get a big laugh 10% of the time and nothing 90% of the time. You want it to be consistent.”

“And in standup, you never know what you’re walking into,” he adds.

For example, Kiley said he performed before a senior ciitzen’s group in Laguna Woods a few weeks back, where the audience stood up and said the pledge of allegiance before the show.

“I’d never seen that before,” he said.

He did say that one change he’s noticed in audiences over his career is that older people are more accepting of risqué material.

“75 is a lot different than 85,” he observed. “Naughty no. But a little risqué is okay. They don’t want it squeaky clean.”

Playhouse 395 was founded some ten years ago by Jeff Pratt, a teacher at Bishop Union High School who rebelled against the idea of the drama club being shuttered and the green room turned into a storage area for football gear.

According to Artistic Director Martha Reynolds, the group is entirely self-supported, and has never received money from the Inyo Council for the Arts or Inyo County.

It works in partnership with Bishop Union High School to maintain and improve the theater.

Playhouse 395 focuses primarily on musicals. In the fall, it produces a youth musical and in the spring, a community musical – this year it’s Oklahoma!

In the summers, the group puts on Children’s Theater Workshops.