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We Had a Little Real Estate Problem

The Unheralded Story of Native Americans & Comedy



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About The Book

A Best Book of 2021 by NPR and Esquire

From Kliph Nesteroff, “the human encyclopedia of comedy” (VICE), comes the important and underappreciated story of Native Americans and comedy.

It was one of the most reliable jokes in Charlie Hill’s stand-up routine: “My people are from Wisconsin. We used to be from New York. We had a little real estate problem.”

In We Had a Little Real Estate Problem, acclaimed comedy historian Kliph Nesteroff focuses on one of comedy’s most significant and little-known stories: how, despite having been denied representation in the entertainment industry, Native Americans have influenced and advanced the art form.

The account begins in the late 1880s, when Native Americans were forced to tour in wild west shows as an alternative to prison. (One modern comedian said it was as “if a Guantanamo detainee suddenly had to appear on X-Factor.”) This is followed by a detailed look at the life and work of seminal figures such as Cherokee humorist Will Rogers and Hill, who in the 1970s was the first Native American comedian to appear The Tonight Show.

Also profiled are several contemporary comedians, including Jonny Roberts, a social worker from the Red Lake Nation who drives five hours to the closest comedy club to pursue his stand-up dreams; Kiowa-Apache comic Adrianne Chalepah, who formed the touring group the Native Ladies of Comedy; and the 1491s, a sketch troupe whose satire is smashing stereotypes to critical acclaim. As Ryan Red Corn, the Osage member of the 1491s, says: “The American narrative dictates that Indians are supposed to be sad. It’s not really true and it’s not indicative of the community experience itself…Laughter and joy is very much a part of Native culture.”

Featuring dozens of original interviews and the exhaustive research that is Nesteroff’s trademark, We Had a Little Real Estate Problem is a powerful tribute to a neglected legacy.


Jonny Roberts Drives Five Hours to Every Gig and Five Hours Back Jonny Roberts Drives Five Hours to Every Gig and Five Hours Back
For an Ojibwe social worker and part-time stand-up in the Red Lake Nation, getting to the closest open-mic night requires an arduous five-hour drive. Jonny Roberts says good-bye to his wife, two children, and eight young foster kids before departing on this exhausting routine. Roberts is driving to Minneapolis to do a show for an audience that might not even show up. It’s a long drive there and a long drive back—a total of ten hours—but it’s the only way for this reservation comic to get himself some stage time.

After having logged several hundred thousand miles driving vast distances from gig to gig, his 2004 Chevy Silverado has stopped working. Roberts thinks the transmission is probably dead. He borrows his wife’s black Dodge Nitro this afternoon and heads in the direction of Highway 89. “It’s pretty much farmland all the way until Saint Cloud, Minnesota,” says Roberts. “There are a few malls and gas stations, but mostly it’s a lot of nothing.” As he drives past the water tower with the Red Lake Nation insignia, he stops at the Red Lake Trading Post to fill up the tank. It’ll cost $120 to get him to the gig and back—a gig that pays zero dollars, and will last seven minutes.

Red Lake encompasses eight hundred thousand acres of mostly flat landscape. Roberts grew up here, obsessively recording stand-up comedians off of television, hoarding VHS tapes of the 1980s comedy boom. Commuting is his only option. He has few neighbors who share his passion. “They’ve tried comedy shows at the casino here, but it’s hard to get people to come out. There’s not much interest for comedy shows in this area and not much opportunity for stage time. So I take the two-hundred-sixty-mile trip for the experience.”

There is resilience in Red Lake, yet the reservation reels from intergenerational trauma in the form of addiction and suicide. A survey by the Minnesota Department of Health and Education determined that 48 percent of high school girls have attempted to end their life, and 81 percent have considered it. In a community with fewer than two thousand people, friends, neighbors, and family members are affected. In his capacity as a social worker, Roberts is only too familiar with the issues. As he heads toward the highway, he drives past a series of homemade billboards created by local schoolkids as part of a class project: UP WITH HOPE—DOWN WITH DOPE and IT’S LIFE—OR METH.

Thirty miles into the commute he enters Bemidji, Minnesota, and stops for a bathroom break. Down the street is a statue that stands eighteen feet tall. Made of concrete and plaster, the roadside attraction known as Paul Bunyan and Babe the Blue Ox has adorned thousands of postcards since 1937. Now armed with a bag of packaged popcorn, Roberts takes U.S. Route 2 out of the city and fumbles with a phone cord. He cues up a playlist of podcasts—WTF with Marc Maron, Urban Indianz hosted by Gabriel Night Shield, Red Man Laughing hosted by Ryan McMahon, and the Monday Morning Podcast with Bill Burr. He has four more hours to go.

Arriving in Minneapolis just as the sun is setting, he walks into the Spring Street Tavern, where fifteen young comedians are milling about. There are nine people in the crowd. Roberts sits in a corner, reviewing a notepad, scratching out some topics and adding others. Tonight is his first bout of stage time in forty-seven days.

Ninety minutes later, he’s onstage telling jokes. “I think it’s great that Bruce Jenner transitioned to Caitlyn Jenner,” he tells the sparse crowd. “But I don’t think she should have picked a young woman’s name. I mean—she’s seventy years old. Are you kidding me? Her name should be Gladys.”

After the show, the other open-mic comedians are hanging out, smoking joints, talking about their next gig, but Roberts is already gone. He has to take his houseful of kids to day care in the morning. It’s 11 p.m. and there’s a five-hour drive ahead of him.

“I’ve been doing stand-up for eight years,” says Roberts. “Sometimes I think I should just quit.” Compared to his contemporaries in Los Angeles and New York, the amount of stage experience Roberts has is minimal. In New York, a comedian with eight years of experience can get onstage every single night. Someone who’s really hustling can do as many as six shows in a single evening. Roberts is lucky if he gets onstage once a month. That makes it hard to move forward. Most open-mic hopefuls are between the ages of eighteen and twenty-three. Roberts is in his early forties. “It’s an advanced age for sure,” he says. “Although they said Rodney Dangerfield went back to comedy at forty-four. So that’s always in the back of my mind.”

Some of his ambition is motivated by a desire to get away from his job, and some of the things he has seen as a social worker have left him shaken. “I just want to walk away from the things I read about in the files. I just want to walk away from what I see on a daily basis.… I don’t know how much longer I can deal with this.… I have no outlet.” Roberts hopes stand-up is the answer.

About The Author

 Kliph Nesteroff is the author of We Had a Little Real Estate Problem.

Product Details

  • Publisher: Simon & Schuster (February 15, 2022)
  • Length: 336 pages
  • ISBN13: 9781982103057

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