Comedian Charlie Hill was the first Native comedian to appear on late night television. The picture is a still shot from his first appearance on "The Richard Pryor Show" in 1977. The book by Kliph Nesteroff, dubbed "The Human Encyclopedia of Comedy," released in 2021, focuses on Native American humor. The book title is drawn from a punchline by Hill, "We had a Little Real Estate Problem." (Source: YouTube)

The most famous punchline in comedian Charlie Hill’s stand-up routine is now the title of a new comedy book.

This story also appeared in Indian Country Today

“My people are from Wisconsin,” Hill would say. “We used to be from New York. We had a little real estate problem.”

Hill, in fact, is a central focus of the new book, “We Had a Little Real Estate Problem: The Unheralded Story of Native Americans & Comedy,” by Kliph Nesteroff, a non-Native writer with decades of experience as a stand-up comedian, comedy historian and author.

Nesteroff had been asked to write a book about a broad swath of comedy in the digital age. One of the chapters he pitched was on Native comedy and how groups like The 1491s have become successful by posting comedic sketches online.

“The publishers were more excited about that one chapter than anything else, so the focus became a whole book on the untold history of Native comedy and comedians,” Nesteroff told Indian Country Today recently by phone from Los Angeles.

The book, released earlier this year by Simon and Schuster, digs deep, going back to the late 1880s and the Wild West shows, when Indigenous people were often forced to tour. Such acts slowly turned to vaudeville and burlesque-type shows.

Then came Cherokee humorist Will Rogers, whose popularity by the 1930s got his message out widely in newspapers and on the stage before he was killed in a plane crash in 1935. Rogers gets a strong reveal in the book as a biting activist instead of the folksy cowboy he has come to represent.

By the 1970s, Hill had taken the lead. A citizen of the Oneida Nation of Wisconsin, he was the first Native comedian to appear on “The Tonight Show,” and on shows hosted by comedians Richard Pryor and David Letterman. Both Pryor and Letterman had been rising comedians along with Hill in Los Angeles in the 1970s, and made good on promises to help each other as their stars rose.

Hill, who died in 2013 at age 62, helped clear the way for the next generation.

Among those featured in the book are Jonny Roberts, known as Jonny R, the Ojibwe Outlaw; Kiowa-Apache comic Adrianne Chalepah, who founded the Native Ladies of Comedy; and The 1491s, the successful sketch troupe whose members have branched into such sitcom hits as “Rutherford Falls,” and theater shows, “Between Two Knees.”

But Hill remains central to the book. Nesteroff said he never met Hill but has the blessing of Hill’s family to use his joke as the title; he tells Hill’s story in tantalizing chapters broken up by other comedians’ stories.

“I had initially written the book chronologically,” Nesteroff said, “but the editors felt that Hill was such a major breakthrough figure – appearing on national TV in ribbon shirts telling Native joke monologues – that we had to draw the story out until the end of the book. He opened the door to the mainstream.”

But as the saying goes, “comedy is tragedy plus time,” and so, too, goes Native humor. How to make genocide funny? How to make a race thought to be extinct and merely mascots relevant?

“I had to tell the harsh truths about Native history in the U.S.,” Nesteroff said, “but balance that with how it became comedy. I didn’t want to be too depressing about it but had to relay it in the way that it became comedy material.”

The book has drawn praise from critics, including The New York Times, which described Nesteroff as “the premier historian of comedy because of his knack for unearthing forgotten stories.”

David Treuer, the Leech Lake Ojibwe journalist and author of “Rez Life” and “The Heartbeat of Wounded Knee,” described the book as a “gem,” according to Simon and Schuster.

“He chips away at the myths of the stoic or long-suffering fate of ‘The Indian,’” Treuer said. “In its place, he creates a vibrant counter-narrative that exposes the hilarious, irreverent, ambitious heart of modern Native America.”

‘Human Encyclopedia of Comedy’

Nesteroff, a native of British Columbia in Canada, started out as a stand-up comic but gave it up after eight years to pursue writing, television and radio.

Now living in Los Angeles, he has worked as a contributor to WFMU radio and CBC Radio One, and has appeared regularly on National Public Radio affiliates.

His first book, “The Comedians: Drunks, Thieves, Scoundrels and the History of American Comedy,” was released in 2015 to high praise in literary circles, drawing a nod from Kirkus Reviews as a “love letter to the funny business.”

Vice Magazine dubbed him “The Human Encyclopedia of Comedy.”

His latest book takes the same deep look at Indigenous comedy, where each generation has faced its own challenges. The book pulls in how the comedians were involved in the major movements of their time and how that influenced their work.

Hill became friends with actor/singer/activist Floyd Red Crow Westerman, activist John Trudell and actor Max Gail, all of whom were involved with the beginnings of the American Indian Movement. That allowed Hill to speak with direct experience about both past and contemporary Native issues.

Trudell’s borderline comedic manifestos that he issued on Radio Alcatraz are reprinted in the book to show how he tried to make sarcastic fun of broken treaties.

Hill started his career when he read Vine Deloria’s book, “Custer Died for Your Sins,” when he was 18. The biting humor made him realize comedy was his future. But how to get there from Wisconsin? And how to reconcile shows he watched like “The Lone Ranger” where the Indian was mostly a silent – and not very funny – sidekick?

A new book, “We Had a Little Real Estate Problem,” by one-time comic Kliph Nesteroff, takes a close look at Indigenous comedy from the 1800s to today’s internet circuit. (Photo courtesy of Simon and Schuster)

He got a job at a radio station in Green Bay, Wisconsin, and filled the air time with jokes. He then joined the American Indian Theater Ensemble in New York, and soon was doing stand-up in Greenwich Village. That led to the Comedy Store in Los Angeles, where he met Pryor and Letterman.

Jonny R faced different challenges. A social worker from the Red Lake Nation, he often drives five hours to the closest comedy club while helping take care of eight foster children and two of his own.

He calls his cross-country trek “The Bad Decisions Tour,” and riffs about pop culture.

Women enter the picture later on. Nesterhoff thinks the harsh demands of travel to questionable venues and the time away from home in the early days of comedy kept women away.

Chalepah, who grew up on the Kiowa/Comanche/Apache reservation in Oklahoma, toured with the 49 Laughs Comedy group before founding the Indigenous women’s troupe, Ladies of Native Comedy. Her website notes she “has been getting in trouble for her mouth as long as she can remember,” and was suspended from school for being a class clown.

A mother of four, she balances home life with travel from her home base in northwest New Mexico. Her stand-up comedy draws on her small-town roots and the culture shock she experiences in bigger cities, and how Natives react to hippies, cowboys, urban cowboys and city slickers.

She’s also featured in “Rutherford Falls,” the hit show on Peacock that features Native actors and writers.

The 1491s — named for the last year before Columbus reached America — are a five-man sketch troupe that started with an online video. The troupe includes Sterlin Harjo, a Seminole/Muscogee filmmaker; Ryan Red Corn, Osage, a graphic artist and photographer; Migizi Pensoneau, Ponca/Ojibwe, a television and film writer and producer; Dallas Goldtooth, Mdewakanton Dakota/Dine, a writer and artist; and Bobby Wilson, Sisseton Wahpeton Dakota, a visual artist and actor who also is involved in “Rutherford Falls.”

“The American narrative dictates that Indians are supposed to be sad,” Red Corn said in a statement released by Simon and Schuster. “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.”

Looking Ahead

The rise of cable channels, Indigenous film festivals, and internet outlets has made the entry into Native comedy easier than it’s ever been.

Today, The 1491s and filmmakers like Steven Paul Judd are able to use YouTube to get their filmed sketches out in ways that Will Rogers and Charlie Hill never could.

Standing Rock has also become an unlikely mass Indigenous connection.

“I was super tired but my mind was on fire,” Wilson recalls in the book. “You’ve got hundreds of tribal nations coming together, you think about the historic context, many of these nations had never interacted. It was a movement of prayer but then the non-Native hippies came in, so we decided to give them all ridiculous Indian names. It was a joke, but this is what we do in stressful situations. We tease each other.”

Harjo says in the book that he got his first calls to work in TV after Standing Rock made front-page and nightly news. Hill’s early TV appearances can now be seen with one click.

“I started out writing about every Native comedian,” Nesteroff said, “but it became like an encyclopedia. I had to focus on the ones that really made strides in the field. It became a much richer, deeper story than I imagined.”