Dick Gregory and Tim Boxer
at the Chicago Playboy Club 1961
Power Of Publicity Rocketed
SHOWED the world what the power
of publicity can achieve when I discovered Dick Gregory and
launched him in orbit in Chicago 1961. I was a reporter for City
News Bureau, a newsgathering cooperative that fed fast-breaking
police news to the newspaper and television news desks. At the
same time I wrote an entertainment column for the
Near North News, a
widely read weekly that covered the Gold Coast and Near North
One night on my regular rounds on Rush Street,
Chicago’s glitzy showbiz district, I heard gales of laughter
coming from the Fickle Pickle, a college hangout. I waved to the
owner, ordered a tea (the joint had no liquor license) and
listened to a comic I’d never heard before.
“Nothing’s free these days,” Dick Gregory was
saying. “You can’t even hate me free. Costs two hundred and
fifty dollars to join the Ku Klux Klan — and you still got to
buy your own sheets.” He had everyone in the white crowd
“I sat at a lunch counter for nine months. Then
they integrated and didn’t have what I wanted.” Here was a wit a
college kid could relish, and these young intellectuals were
roaring all through his act.
His incisive humor was so captivating that I
stayed after the show. We talked late into the night. I told him
how fascinated I was with his act, so insightful, that he
belonged in the top tier of show business, not in an obscure
He told me how he’d been working all the Negro
night spots on the South Side, including the famous Roberts Show
Lounge. “But that’s not where it’s at. I can stay there the rest
of my life. But I won’t get anywhere and I won’t make any money.
What I need is to break into the white nightclubs uptown, like
Mr. Kelly’s or the Playboy Club.”
“Don’t you have a manager?” I asked.
“I’ve had plenty of offers from Negro managers,”
he said, “but I don’t want anything to do with them.”
Mighty strange talk
coming from one who claims to speak up for the
“The Negros can’t help me,” he explained. “They
don’t know how. All the prestige clubs are owned by the Jews.
Negro managers can’t get through the door.”
As he saw it, the only one who could help him
would be a manager with two essential attributes: white and
Jewish. “They’re the only ones who can get me into the top rated
lounges. The Negro managers don’t have the know-how or the
connections. It takes a Jew to open the door.”
In all my wanderings along the nitery circuit, I
was unaware that Jews held all the power in the entertainment
world. In fact many of the major clubs were run by Italians,
Greeks, Irish and others besides Jews. I didn’t care to argue
the point with someone steeped in stereotypes. I saw Gregory as
the vanguard of a new type of cerebral black entertainer — not
the tired buffoonery of Amos ‘n Andy — and I jumped at the
opportunity to jumpstart this revolution in American show
It was fate that the greatest comedy find of the century shook
hands with a man who fit the racial requirements of a press
agent whose mission was to launch him to the heights of show
business with the simple device of publicity.
Dick Gregory 2016
“We’ll make it together,” he said as we bonded.
Money was no consideration; enthusiasm was all. He gave me his
word that he’ll compensate me eventually. After all, what could
I ask from someone who was making all of five dollars a night at
a coffeehouse? Such mundane matters as my fee were deferred for
future deliberation. I was excited to promote what I saw was a
superstar ready to orbit. That night I morphed from City News
Bureau journalist to self-taught publicist. It wasn’t difficult
— it just takes chutzpah.
Gregory already had an agent, Associated Booking
Corporation, headed by Joe Glazer in New York (whose ethnic
credentials fitted in with Gregory’s plan). The Chicago office
was handled by Freddie Williams, a formidable Irishman. They
were able to get Gregory bookings in spots that mostly catered
to black audiences. Apparently they did not see his potential
further than his home base.
I gave up my two newspaper gigs to hang with
Greg. Then it happened. The regular comedian at the Playboy Club
took ill. It was a Saturday night when the showroom is usually
sold out. Victor Lownes, Hugh Hefner’s right-hand man in charge
of entertainment, was in a panic. Williams saved the day by
offering to send Gregory, a complete unknown, to fill in. Lownes
had no choice.
As fate would have it, the room filled up with
frozen food conventioneers from the South. Undaunted, Gregory
bounced on stage and smoothly won them over with his brilliant
quips and profound observations of our social ills and
prejudices. They never heard wit like this before, especially
coming from a black man. Every line drew bursts of raucous
laughter. Gregory electrified the audience — he killed!
The thunderous applause confirmed my instincts.
This man is a star! He belongs on this stage. I can’t let this
one-nighter pass into obscurity. This is a break that may never
happen again. My heart was racing.
I ran to the house phone and asked for Victor
Lownes. The operator said sorry, he was not in the club. My
heart sank. I insisted she call him at home. I knew I was
intruding on his privacy —on a Saturday night! — but I was
determined to seize the moment. I held the phone in the air so
he could hear the boisterous reaction of these southerners to
Gregory’s topical humor.
As a Niagara flow of applause flooded the
showroom Lownes asked, “What’s his name?”
“Dick Gregory,” I said. “You put him in here for
one night. You have to come over and see how sensational he is.”
Lownes came and looked and booked Gregory for a
three-week engagement. That made me the world’s busiest praise
agent — pushing Gregory’s witticisms (and name) to the Chicago
newspapers on a daily basis. It wasn’t hard when you’re working
with brilliant material. The lines at the club started forming
every day. Lownes was forced to extend Gregory’s show for a
second three-week run, then a third.
Every midnight I ran around to the newspaper
offices. I was a familiar sight to the night guards as I dropped
off envelopes of Gregory’s humorous lines on the desks of the
city’s major columnists. Every morning I showed Gregory how the
press was promoting his name as the town’s new star. All the
columnists eagerly cooperated — actually competing with each
other —as they welcomed these items to spice up their columns.
The first columnist to break Gregory’s name in
print was the Chicago
Tribune’s Herb Lyon who enthused, “Hottest and most unusual
new talent in show biz is a young Negro comic, Chicagoan Dick
Gregory, who works in the satirical manner of Mort Sahl, Bob
Newhart and Shelly Berman. He grabs his material from the
headlines and is an overnight smash at the Playboy club’s
Irv Kupcinet of the
Sun-Times, who loved
Gregory’s satirical comedy, said he was the talk of the town.
Tony Weitzel in the
Daily News tabbed him
as the Negro Will Rogers. “In the Congo,” Gregory responded,
“they call Mort Sahl the white Dick Gregory.”
barrage of publicity brought out the hard-nosed critics.
Their reviews were totally ecstatic.
My ardor knew no bounds. I reached for the summit —the local
bureau of Time
magazine. I invited them to see for themselves. No response. I
called again. I knew that the tsunami in the newspapers will
force them to change their mind. They came, they saw, they gave
Gregory an entire page. That made Gregory a star and I was
walking in the clouds.
GREGORY STORY ON STAGE
Hefner gave me credit for the cultural upheaval I masterminded
in Chicago. In his introduction to Gregory’s first book,
From the Back of the Bus (Dutton 1962), he described how “a
young, inexperienced, but inexhaustible press agent, Tim Boxer,
badgered a Time magazine writer into watching Gregory
work,” which resulted in a feature article brimming with “lush
praise.” (Hefner admired my efforts to the extent that he
directed Lownes to appoint me his public relations director in
New York for the new Playboy Club and magazine.)
The public clamor enabled bigtime New York agent
Joe Glazer to get this Chicago phenomenon
Jack Paar Tonight Show
for his first national TV exposure, followed by a clutch of plum
bookings in the uppermost clubs, such as the upper crust Blue
Angel in New York and the fabled hungry I in San Francisco.
Gregory made it. His dream was coming true.
called it “an historic breakthrough in show biz annals” which
made Gregory “the first standup comedian of his race to crack
the plush intimery circuit, and in such force.” The bible of the
entertainment industry went on to acknowledge how I discovered
Dick Gregory and made him a star overnight:
"Owing to the almost daily raptures of several
Chicago columnists, career of young Negro comedian Dick Gregory
is streaking off the launching pad like a Canaveral success.
Leading the stampede for Gregory, Windy City scribes have shown
a virtual mania to “item” the comic, and the result has been a
skyrocket that has even blasé tradesters impressed. Consensus is
that, for the comparable stage of development, Gregory outcomets
Bob Newhart, another Chi product. Comic already has a press
agent, however, and almost without saying."
Years later at a party in Los Angeles, Bill
Cosby thanked me for my efforts on behalf of Dick Gregory, who
broke the ceiling and made it possible for Negro standup
comedians to follow. Not until I vaulted Gregory to the heights
of superstardom were black standups welcome at the sophisticated
clubs for the
first time in the annals of American culture. As Hefner noted, I
was instrumental in helping Gregory become the first Negro
comedian to make his way into the nightclub big time. It was a
significant moment in the civil rights revolution, little known
by the public but acknowledged to me by such prominent African
American comedians as Nipsey Russell and Timmie Rogers as well
as Bill Cosby.