CHET CHESHIRE, the WONDERLAND M.C. and his feline and real-life inspirations


The musical “Speakeasy” begins in darkness.  The overture has concluded, all lights have dimmed, we can’t see anything and all we hear is a chime like tone (on an octave of G). Then a tiny spotlight reveals a debonair smile.  The light broadens to frame the top-hatted head of Chet Cheshire, the Master of Ceremonies of the Wonderland nightclub.  He sings the musical’s opening number, also called ”Speakeasy”:

Chet Cheshire serves a special function in the musical “Speakeasy – the Adventures of John and Jane Allison in the Wonderland”.  As the M.C. of the Wonderland nightclub in New York during the Roaring Twenties he is perfectly situated to sing those songs that establish the themes and moods of the speakeasy and the musical itself, as well as slyly comment on the action enfolding in and about the Wonderland.  And as “Speakeasy”, inspired by Lewis Carroll’s Alice books, is a decidedly magical realist affair, Chet Cheshire also has the power to bend time and space to his whims and flit in and out of scenes at will, playfully complicating and manipulating the actions of our hero and heroine, John and Jane Allison.

As such the character Chet Cheshire lives in a musical theater tradition that includes such famous characters like the M.C. from Cabaret, the Leading Player from Pippin or El Gallo from The Fantasticks, to name a few.  These are characters that act as narrators of or commentators on the action, that help set the world and feel of the musical and guide the audience inside.  Although they may get involved in the plot, they mostly tend to stand separate or above the rest of the characters.  They also are more likely to break the “fourth wall” and share a special relationship with the audience that the rest of the cast doesn’t.

Gene Malin

Gene Malin

When Chet Cheshire sings the opening number “Speakeasy”, we recognize him to be the impresario in a nightclub we will eventually learn is called the Wonderland.  It may not be clear at this moment whether Chet is singing only to the imaginary patrons of the Wonderland in 1929/1930 or whether the actual contemporary audience is included.  But eventually the audience will recognize that Chet is speaking to all who can hear and see him.  More quickly the audience will note that Chet’s name evokes the Cheshire Cat from Alice in Wonderland.  What most will not know (at least not without looking at the program notes) is that Chet is also inspired by the real life performer Gene Malin.

The Cheshire Cat is probably the most famous of the many strange characters Alice meets in her adventures in Wonderland and Through the Looking Glass.  More than any denizen of Wonderland, he appears to have the clearest sense of the place:

‘ “We’re all mad here.  I’m mad.  You’re mad.”

“How do you know I’m mad?” said Alice.

“You must be,” said the Cat, “or you wouldn’t have come here.” ‘

The Cheshire Cat confounds the King and Queen

The Cheshire Cat confounds the King and Queen

He also appears and disappears at will, with his smile and his head first to be visible, and last to vanish.  As such he tends to stand apart from the rest of the Wonderland characters.  During the croquet scene he literally rises above all, his disembodied head floating above the fray, blithely impervious to the Queen’s demand that they be “off with his head”.

Chet Cheshire too will appear to Jane and then John Allison as unexpectedly and magically as the Cheshire Cat does to Alice.  He will whimsically needle both with questions and remarks that will nudge both on their separate paths towards the Wonderland nightclub and self-discovery.  He will also prove himself elusive to the authorities’ grasp when they finally try to take action against him.

Gene Malin

Gene Malin

Gene Malin was the most famous performer of the short-lived Pansy Craze of 1929.  A six foot, 200 pound fellow who was unabashedly flamboyant and effeminate, Gene worked as a drag performer (as Jean Malin or Imogen Wilson) in West Village clubs after stints as a Broadway chorus boy (reportedly he kept losing chorus boy jobs because he was too effeminate).  He made the big time during the so-called “Pansy Craze” of 1929 when major Times Square nightclubs hired “lavender” acts to give the upscale crowd a taste of the Village or Harlem Queer scene.  Gene Malin’s act was to be his own unabashedly flamboyant, effeminate self, not in drag but in a tux, yet unapologetically swishy, elegant and witty.  Often audience members would taunt him, but to their own peril.  The most popular part of Gene’s act was the devastating way he put down his homophobic hecklers.  He was also big and strong and not afraid to defend himself with his fists.  There are several stories of him getting the better of those who would try to bash him.

Gene (Jean) Malin autograph

Gene (Jean) Malin autograph

The Pansy Act wouldn’t last long – nightclubs soon realized that employing “lavender” acts made them more prone to police raids – and eventually the end of Prohibition and the stricter social policing of the 1930’s made life very difficult for openly homosexual performers.  But Gene Malin at least avoided that fate; he was still the highest paid nightclub performer at the time of his death at the young age of 25 in 1933.  After performing a “farewell performance” at a club in Venice, California he presumably gear-shifted incorrectly and accidentally drove his car off the pier into the water.  He was killed instantly.

There are a few fascinating records and a pre-code film clip of Gene Malin singing and doing drag; but by most accounts the greatest draw of his performance was Gene simply being his mercilessly witty, unabashedly Gay self.  “Speakeasy’s” version of Gene Malin, Chet Cheshire, recreates Malin’s irreverent act, but also makes Chet a singer who can croon like Bing Crosby or belt like Nelson Eddy, embracing all singing styles of his era.  And like the Cheshire Cat, Chet is imbued with more than a little ineffable magic.


To read more about Speakeasy, check out The Speakeasy Chronicles from the Category tab to your right.  And to listen to more Speakeasy demo recordings, venture here.

About dannyashkenasi

I'm a composer with over 40 years experience creating music theater. I'm also an actor, writer, director, producer, teacher and general enthusiast for the arts.
This entry was posted in LGBTQ Alphabet Soup, The Speakeasy Chronicles and tagged , , , , , , , , , , , , , . Bookmark the permalink.

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