One night in the mid-1980s, Karen Pickering’s mom decided to prepare her daughter for the real world. That meant men.
Her mom’s abusive second husband was out of the picture by the time the two of them stood in a San Diego kitchen, roleplaying how Pickering could handle different scenarios.
Pickering was working as a radio DJ, and starting to hear “horror stories” of what friends from the University of Minnesota were going through in their first professional gigs. “We didn’t have HR departments,” she says.
As she began to try her hand at standup comedy, Pickering combined her mom’s techniques with her own: pay attention, act tough, park near the club under a street light.
Pickering moved back to Minnesota to live with a Joey Ramone lookalike from New Jersey. They both loved Bon Jovi. She soon realized she’d made a “wretched mistake,” one she mined for material. The new stuff was a hit.
“It was real, and the audience senses that,” Pickering says. “And it’s funny, because everyone’s done dumb shit.”
Pickering spent hours at public libraries, reading news stories and writing jokes. She arrived at clubs with a briefcase-full, and recorded all her sets to play back later. She did a bit about handing first dates a questionnaire — “Do you have a checking account?” — and another about the chances Nancy Reagan’s “skinny little neck” would someday get sucked up into the blades of the Marine One helicopter.
One time, a big-name local comic said something “inappropriate” to Karen.
“You should lose some weight,” she shot back, “or I’m going to be a pallbearer at your funeral.” Pickering never opened for him again. “I think I had a reputation for treating everything like business, and being a real bitch,” she says.
During the day, Pickering sold office supplies. She saved PTO and vacation days for gigs in Denver and Chicago. Often, “some low-grade comic” followed her to her car. Guys guessed any woman alone on the road was up for something. Pickering turned them down or told them off.
By the early 1990s, Pickering was “featuring” — the last comic to go on before a headliner — and making trips to New York, where she knew talent agents and casting directors pulled nobodies from the stage for their big break.
After one show, a friend, someone she’d known for years, had her boyfriend walk Karen to her car. “I don’t need to tell you what happened,” she says.
Pickering had done everything right. Played it cautious, looked out for herself, avoided weird scenes, used the buddy system, and didn’t trust strangers. She still wound up “pretty beaten up” at a New York City police station, telling a cop a story, and the name of her rapist. If police or prosecutors pursued the case, they didn’t bother to inform Karen.
Back in Minnesota, she put standup “on the backburner.” She went to therapy, working through post-traumatic stress and “a lot of anger.” She quit the nightclub circuit. She played a few corporate gigs in small, safe, private settings, then stopped doing even those.
“It did kinda take away a dream,” she says of her assault.
Pickering shifted her attention to family and career. Well, careers: After selling office supplies, she worked as an assistant manager at a chain of gyms, supervisor for the restaurant at a Macy’s in Burnsville, and a school lunch lady. Today, she sells shoes.
Earlier this decade, as Karen’s teenage kids flipped through a scrapbook, they learned of their mom’s comedy heyday. They told her to try again.
After 20 years away from the business, Karen’s encore came at a cancer benefit a friend was organizing in Rush City. She still plays that benefit, slotting it into ever-busier weeks at open mics and comedy contests.
She tells jokes about marrying a Minnesotan — “the Lutheran,” she calls him — and the drunken, debauched sights of the Minnesota State Fair, when we let our “inner Bostonian” out. She talks a mile a minute, saves the sex stuff for the later (drunker) crowds, and knows how to turn an audience against the table of loudmouths before they ruin everyone’s night.
Comedian Rana May recognized Pickering's comfort onstage the first time she saw her at an open mic. May didn’t know Karen’s story, but knew she liked how humble she was.
“Oh, I’m rusty,’” Pickering would tell May, who says Karen’s act “made being a mom who lives in the suburbs relatable, and that’s not a viewpoint I’ve ever even wanted to have.”
May invited Pickering to join an online network for women-only comedians, a support group that sometimes warns women about predatory men.
May sees comics like Pickering — “a great, supportive, conscientious person” — as having come of age in an in-between period. Women learned to be “tough,” and protect themselves, but when men did bad things, they had nowhere to turn. Pickering doesn’t disagree.
“I feel like we enabled a lot of things, because it was the way to keep our jobs,” she says. “We had ‘women’s lib’ in the ’70s and… what the hell happened?”
The culture has finally advanced, slightly. Even comedy has moved forward — see: the swift downfall of Louis C.K. — albeit in lurching, ugly steps. Pickering loves the sisterly streak she sees in young comics like May, and admires how entrepreneurial this crop of women is. If this is the new comedy industry, she wants to be part of it.
“It’s more than a hobby for me now,” she says. “I’d like to get my material tweaked a little — then save up my PTO and vacation days, and take some risks.”
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