To the extent Will Rogers is known today, it’s as the folksy founding father of topical political comedy, the first comic to tell jokes about the president to an audience including the president. Woodrow Wilson apparently could take a joke.
What’s often overlooked about the early-20th-century superstar is that he was Native American, a fact centered and explored in Kliph Nesteroff’s new book, “We Had a Little Real Estate Problem: The Unheralded Story of Native Americans & Comedy.” Nesteroff doesn’t just map a direct line from Rogers’s Cherokee roots to his political perspective; the author reintroduces Rogers as an altogether modern comic: moody, depressive, with uglier prejudices than his aw-shucks image would indicate.
Nesteroff digs into an episode in which Rogers faced a backlash for using a racial slur about Black people on the radio in 1934. This led to denunciations in newspapers, protests and boycotts — with Rogers stubbornly doubling down a year before dying in a plane crash. “That story was scrubbed from history books,” Nesteroff told me in a video interview.
In recent years, Nesteroff, 40 and often seen wearing a fedora, has carved out a niche as the premier popular historian of comedy because of his knack for unearthing such forgotten stories.
A meticulous collector of showbiz lore, Nesteroff filled his 2015 book, “The Comedians: Drunks, Thieves, Scoundrels and the History of American Comedy,” with fascinating detours about obscure figures like Jean Carroll and Shecky Greene. One of his early articles that got attention was a 2010 blog post about Cary Grant’s enthusiasm for LSD. Then relatively unknown, the movie star’s drug use has since made its way into Vanity Fair and even a documentary.
“Now I wouldn’t write about it,” Nesteroff said, saying he gets annoyed by histories that keep going over common knowledge: “I want to write about the details people don’t know.”
His new book, which darts back and forth in time, is a sprawling look at Indigenous comedians, an overlooked branch of comedy. The book’s title (“We Had a Little Real Estate Problem”) is the punchline to a joke by the unsung hero of this narrative, the Oneida Nation comic Charlie Hill. (The setup: “My people are from Wisconsin. We used to be from New York.”) A contemporary of David Letterman and Jay Leno in the Los Angeles comedy scene of the 1970s, Hill was a handsome performer with superbly crafted jokes who became one of the few famous Indigenous stand-ups. Nesteroff writes that Hill was the first and only such comic on “The Tonight Show.”
On his network television debut, on “The Richard Pryor Show,” Hill delivered a tight, five-minute set that skewered Hollywood stereotypes of Native Americans and described pilgrims as “illegal aliens,” likening them to house guests who won’t leave. Hill performed for three more decades and was a stalwart at the Comedy Store (although he barely received any airtime in the recent five-part documentary on the club), inspiring many Indigenous comics. “What Eddie Murphy was in the ’80s for young Black comics, that’s what Charlie Hill did for new young Indigenous comedians in the last 15 years,” Nesteroff said.
And yet, while there are many more Native American comics today, including the members of the sketch troupe 1491 that Nesteroff chronicles in his book, mainstream opportunities remain scarce. “When we hear diversity in Hollywood, Native Americans are seldom included under that umbrella,” Nesteroff said. “That needs to change.”
His book provides context for an argument about the importance of representation, detailing an exhaustive history of the racism suffered by Indigenous people in popular culture, tracking stereotypes of the stoic, humorless Native American from pulp fiction and animation (which was particularly egregious) to “I Love Lucy” and “Dances With Wolves.”
Nesteroff begins his book describing growing up in Western Canada, where images of Indigenous artists, he says, are more common than in the United States. For years he worked as a stand-up comic, and confesses he still misses performing. He got sidetracked after his online posts about showbiz history drew attention. An appearance on Marc Maron’s podcast in 2013 led to his first book deal.
Back then, he balked at being called a historian. “That’s what a boring person does,” Nesteroff said, summarizing his previous prejudice rooted in a checkered academic career. (He was expelled from high school for roasting teachers in a speech for school president.) But he has since embraced the term, even saying it’s “his role to educate people,” and he has done so as a talking head on CNN and Vice.
Nesteroff still has the instincts of a comic. “I always go for the best story because I am still at heart an entertainer,” he said. “My biggest fear is being boring.”
That’s evident from our conversation, which he packs with detail-rich stories and occasional impressions. When asked about his Hollywood neighborhood, he said he didn’t want to reveal it “because of internet fascists,” but immediately started explaining its showbiz history, including a building nearby where an actor from one of the cult director Ed Wood’s movies committed suicide. “People say L.A. doesn’t honor its history, but it’s not true when it comes to residential buildings,” he said. “It’s a status symbol to live in Greta Garbo’s old house. The house from ‘What Ever Happened to Baby Jane?’ was just put on the market.”
Nesteroff prefers writing about the past over the present, but they often blur in his books. In “Real Estate,” he describes protests against white actors playing Native American roles dating all the way to the 1911 film “Curse of the Red Man,” which led to meetings between Indigenous delegations and President William Howard Taft that sound remarkably similar to current controversies. In another chapter, Nesteroff recounts an argument between Will Rogers and the journalist H.L. Mencken from the 1920s, about how much harm comedy can do, that could be taken from any number of podcasts today.
Nesteroff finds that people are amazed to see history repeating itself — “it blows minds,” he said — but like a comic who knows not to make a punchline too on the nose, he declines to draw a connection with the current day. “I’d rather the reader discover it themselves,” he said, before adding that the echoes are definitely intentional.
If there is one consistent theme from his intrepid reporting on the roots of comedy, it’s this: there’s less new under the sun than you think.
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