We Had a Little Real Estate Problem

A nonfiction book by Kliph Nesteroff.

Kliph Nesteroff

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. (From Simon & Schuster)

Kliph Nesteroff is a Canadian stand up comic and comedy historian. His previous book, The Comedians: Drunks, Thieves, Scoundrels and the History of American Comedy, came out in 2015 to positive reviews.

From the book

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.

From We Had a Little Real Estate Problem by Kliph Nesteroff ©2021. Published by Simon & Schuster.

Interviews with Kliph Nesteroff

In 1977, Oneida comic Charlie Hill made his primetime debut on the legendary yet controversial Richard Pryor Show. Hill’s influential career in comedy began with one punchline: “My people are from Wisconsin. We used to be from New York. We had a little real estate problem.” That punchline is now the title of a new book that gives readers an in-depth look into the history of Indigenous comedians, from vaudeville acts to The Comedy Store in Los Angeles. Tom Power talked to Kliph Nesteroff, the author of We Had a Little Real Estate Problem: The Unheralded Story of Native Americans & Comedy, as well as one of the Canadian stand-up comics profiled in the book, Dakota Ray Hebert. 21:00

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