FLIPPING OUT

I just finished reading a biography, Flip, by Kevin Cook (Viking, 2013), about a renowned comedian from half a century ago. The recent Tennessee law which attempts to ban public drag performances—the language refers to “male or female impersonators”—inspired me to look back on the life and work of Flip Wilson, the most famous part-time female impersonator from my own childhood. 

 

It's not that Clerow “Flip” Wilson set out to be a female impersonator. No one would have described him as such. He was a comic. He spent years trying to get gigs to do his standup routine on the Chitlin’ Circuit, a series of venues open to having Black performers, as well as in places in the western U.S. In Stockton, California in 1954, he stumbled upon a hit routine, teaming up with a piano player, Charles Calloway. 

Calloway played and sang a brokenhearted blues 

tune. When he got to the chick who done him wrong, 

Flip flounced on-stage in a blond wig and tight skirt. 

Nervous laughter from the crowd as Calloway played 

on, wailing about his girl leaving him for a man with 

a bigger bankroll. Now Flip gave the piano a bump 

with his hip.

 

“Wasn’t just his bankroll was bigger, honey!”

 

The crowd roared. [p. 42]

 

Wilson—and the club owner—knew the routine would keep an audience coming back. There was no taboo to a man donning a wig. As biographer Kevin Cook writes: “[E]ntertainers from Sophocles and Shakespeare to Tony Curtis and Jack Lemmon, then starring in Some Like It Hot, had proved there was a simple[] factor at work: drag was just funny. Wilson constantly tweaked his act, filling legal pads with jokes and analyses. As the fifties rolled on, he’d honed his drag bit into a Black, streetwise version of Queen Isabelle of Spain, initially balking before commissioning Christopher Columbus to sail the seas. (“That’s a lot of money, honey! You want me to hock my crown jewels?”)

 

After grinding it out for years, Wilson’s big break came in 1965 when Redd Foxx, a bigger Black comedian he knew from crossing paths at various venues, mentioned him during an appearance on “The Tonight Show.”

Johnny Carson…asked, “Redd, who’s the funniest 

comedian out there right now?”

Foxx didn’t hesitate.

“Flip Wilson.”

 

The shout-out got Wilson a spot on the show. Carson loved the standup routine and kept inviting him back. Flip Wilson became a guest host on the show, drawing higher ratings than Carson himself. NBC gave Wilson his own special, airing in September 1969, introducing America to what would become Wilson’s most famous character during one of the skits.

Jonathan Winters, cross-dressing as gray-haired, matronly Maude Frickert, boarded a plane 

ruled by a stewardess decked out in high heels, 

a hip-hugging mini-dress, and a wig with a flip. 

“Anything I can get for you, little old broad?” 

the stewardess asked.

 

“Yes,” said Winters-as-Maude. “Get me a 

little old man, Miss…?”

 

“Geraldine,” Flip said. “Geraldine Jones, honey. 

That’s J-O-N-E-S…honey.” [p. 114]

 

As Cook succinctly states, “Here was the coming-out of a character that would dominate Flip’s act and much of the rest of his life.”  

 

Skit with Lily Tomlin as Ernestine
and Flip Wilson as Geraldine

It’s strange trying to make sense of stars with lasting legacies and those who are almost forgotten. I’m surprised how few people, even five years younger than me, remember Flip Wilson. The biography establishes Flip as an entertainer who broke down barriers for Black comedians. In an era when the television variety was popular, Flip Wilson became top in the field when “The Flip Wilson Show” debuted in 1970. It was the number two show of 1970-71 and 1971-72, bested only by “Marcus Welby, M.D.” and “All in the Family” in respective seasons. At a time when there were only three major networks and often only one television per household, Wilson’s show was family viewing for tens of millions of Americans as the lead show for the Thursday primetime lineup. His friends George Carlin and Richard Pryor were both writers for the show which lasted four seasons, accounting for ninety-four episodes and included a wide range of guest such as James Brown, Big Bird, Roy Clark, Lily Tomlin, Perry Como, Louis Armstrong, Marcel Marceau, Aretha Franklin, Tony Randall, Carol Channing, Stevie Wonder, Muhammad Ali, Tim Conway, Paul McCartney, Jim Nabors, Burt Reynolds and Leonard Nimoy.

 

Wilson’s character, Geraldine Jones, was a household name, making the cover of magazines like Jet, Ebony and TV Guide. (Wilson, as himself, made the cover of both Life and Time in 1972.) In one poll, Geraldine Jones beat out Carol Burnett and Mary Tyler Moore as “America’s favorite comedienne.” Her catchphrase, “What you see is what you get,” was especially funny, delivered by a character in drag. 

 

It's hard to imagine that drag is a push-button issue in 2023 when Geraldine Jones was so beloved a half century ago. Cook devotes one paragraph to mentioning what Wilson called a “blacklash” to Geraldine:

To Flip’s consternation, many Black men who 

liked and supported him recoiled from 

Geraldine. “We all watched the show,” one 

recalls, “but I shut it off when he did that part. 

I had sons eight and ten years old, and I 

wasn’t letting them see him dress up as a 

woman. That wasn’t the way to represent a 

Black man.” [p. 145]

One would think that any reticence would have run its course by now.

 

Wilson was undeterred. While he tired of fans constantly asking him to do his Geraldine impression for the rest of his life, he viewed the character as a role model. “Geraldine may not project the image of a refined, sophisticated lady, but she’s honest, she’s frank, she’s affectionate, she’s independent. I think every woman should be like that.” [p. 146]

 

Flip Wilson, who died of cancer in 1998 at the age of sixty-four, was no saint. As a person, he doesn’t even come off as likable. Clerow had to be scrappy during a tough childhood and the years of trying to get by with low-paying gigs. He regularly used drugs, first claiming they helped him write funnier bits and then out of habit or perhaps addiction. He hooked up with many women and was too egocentric and immature to be a decent father. (To be fair, his childhood offered no role models.) Still, I remember watching “The Flip Wilson Show” with my parents and all of us being entertained. He had a cool vibe and used his big eyes to make many of his lines come off as funnier than they were. He had a preacher character who was more concerned with jacking up donations than saving sinners.

 

Lucille Ball & Geraldine

In the eighties, Wilson had a short-lived family sitcom, “Charlie & Co.,” that co-starred Gladys Knight and Jaleel White, the future Steve Urkel on “Family Matters.” But I remember him most fondly for wearing a wig and donning a dress as Geraldine Jones. I wish Geraldine were around today to give drag-fearing politicians from Tennessee and other regions a good talking to.