We Had a Little Real Estate Problem: The Unheralded Story of Native Americans & Comedy

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.

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