Before Dick Gregory’s big break performing at Hugh Hefner’s Chicago Playboy Club, there was Herman Roberts and his Roberts Show Club.

Gregory got his comedy start in Chicago at that club, 6622 S. Parkway. Call it forgetfulness or even erasure. But Gregory had been nurtured and embraced by fellow strivers in pockets of black tenacity before he was invited to ply his comedic wit and social critiques one January night in 1961 at Hefner’s club.

It was a big deal when Hefner came to Roberts’ club to see Gregory. So when Gregory got the call to fill in for a white comedian, Roberts, too, was excited because “this was the first big breakthrough for blacks performing,” wryly noting, “the same thing almost put me out of business.”

Desegregating the local nightclub scene was one for the culture, while setting Gregory up for bigger and better things: What was supposed to be a well-paying, one-night gig famously turned into two weeks, and led to a profile in Time magazine and a “Tonight Show” appearance with host Jack Paar. Gregory had ushered in the concept of “crossover,” black entertainers performing for white audiences. And his success also portended the beginning of the end of the black nightclub scene, as desegregation allowed blacks to spend time and money outside of their communities.

When Richard Claxton “Dick” Gregory died last month in a Washington, D.C., hospital at age 84, obituaries for the St. Louis native tended to skip straight to his being “discovered” while rendering nuanced race-based social commentary before white audiences tickled by his refreshing approach.

But before that, he worked for Roberts, now 93, for $25 a night.

In true Great Migration fashion, Gregory found community, purpose and roots in Chicago that fed his career and his conscience. Even after he and his family moved, he often returned to support social justice causes and political movements, including Harold Washington’s successful 1983 bid to become the city’s first black mayor. Of course, Chicago was a haven for socially conscious black performers, like jazz singer Oscar Brown Jr. and gospel great Mahalia Jackson, who put up the Rev. Martin Luther King Jr. in her Chatham home, according to historian Timuel D. Black.

Wherever he was, Gregory often prioritized fighting for civil rights: He marched in Selma, Alabama, with King, protested the Vietnam War, and years later engaged in hunger strikes for a number of causes, including Middle East peace, the Equal Rights Amendment and ending police brutality.

So much of today’s public conversation about social justice finds antecedents in Gregory’s work and stances. Gregory lost income by taking a stand, just as free agent quarterback Colin Kaepernick is paying the price for taking a knee during the national anthem to protest racial oppression. Where Gregory had faith in his method, Chicago’s Chance the Rapper has exercised his agency to chart a different path in the music industry, and he’s winning. Chance, too, is deeply rooted here, having donated more than $2 million to the financially troubled Chicago Public Schools, the same system Gregory protested to provide a better education for black students over 50 years ago. And where it took the hashtag #BlackLivesMatter to spark a new generation of activists, black life always mattered more than anything to Gregory, even money.

“That was the edge in his comedy; he made racism seem kind of stupid,” says John H. Bracey Jr., chairman of Afro-American Studies at the University of Massachusetts at Amherst, who was a graduate student and activist at Northwestern University when he met Gregory.

Living with wife Lillian and his growing family in Hyde Park, Gregory was naturally drawn to local politics and lent his “vigor” and point of view to local causes, such as education reform, Black says. Gregory ran for mayor in 1967 against Richard J. Daley, says Black, who recalls Gregory working with him and the Chicago Committee, a diverse group of Chicagoans — black, Latino and white — eventually linking up with A. Philip Randolph’s Negro American Labor Council.

A young woman holds a poster reading, “Be quick! Vote for Dick Gregory, Mayor of Chicago,” during a commemoration of the Selma to Montgomery March at George Washington Carver Park in Selma, Alabama on April 9, 1966.

“Dick Gregory was all over the country with comedy acts as well as his performances dedicated to bring about equality and change,” Black says.

Gregory once used his star power to outwit local Mississippi politicians who had stopped distributing food surpluses to poor blacks in the 1960s. Gregory chartered a plane to bring in tons of food, and participated in Student Nonviolent Coordinating Committee (SNCC) sit-ins and voter registration drives.

Gregory, in fact, put up a $25,000 reward for an arrest and conviction in the 1964 murders of civil rights workers James Chaney, Andrew Goodman and Michael Schwerner in Neshoba County, Mississippi, Bracey says.

“He put it in a bank account until someone met the requirements, and we had a couple of fundraisers for the families of the people who got killed,” says Bracey of the case, which wasn’t solved until 2005 when Edgar Ray Killen was convicted of manslaughter for his role in the deaths.

Black, 98, recalls working with Gregory during the Willis Wagon years in the early ’60s. At that time, critics of Schools Superintendent Benjamin Willis protested the overcrowding and segregation of black children, who were crammed into poorly constructed mobile units at schools and on vacant lots, exposing the children to the elements.

West Side activist Brenetta Howell Barrett recalls substandard bathroom facilities in the units that “couldn’t accommodate usage” or “may not have been functioning.” Black parents, activists and groups like The Woodlawn Organization agitated for black children to attend roomier white schools, but the powers that were refused to redraw boundaries to accomplish this.

“He was a very active person,” Black says of Gregory. “During his profession in California, he would come back to Chicago regularly to give leadership to the school boycotts of the 1960s. He came and marched over to the mayor’s house. He would march them over there and protest, then come back to the South Side and make an assessment of how it went.”

The Washington Post recounts the 1965 march from City Hall to Daley’s home where Gregory and “several dozen peaceful protesters were arrested for disorderly conduct.”

Barrett, 85, remembers Gregory joining demonstrations against the Willis Wagons and subsequent school boycotts in 1963 and 1964 as she worked with a coalition seeking adequate funding for black schools, parity in hiring and retaining black teachers and administrative personnel, and “basic things like up-to-date books.” Gregory was known for being an accessible celebrity, speaking at rallies, community gatherings and fundraisers when there was no money to give him.

He “had no compunction” about coming, she says. “Once, he came to a theater on Madison that looked like a stadium full of people. He spent as much time as he would have spent on stage as a feature act, and that was tremendously appreciated.”

Evanston’s Bennett Johnson II, a civil rights activist since his youth, remembers working with Gregory when he was attending Roosevelt University.

“I can’t recall the year, but we were trying to find a candidate for mayor and went to see Dick Gregory near Lake Park,” Johnson says. “We were talking to him, and his kids came into the room. He cursed. He called them m———ers and things like that. We were startled by it, of course, but he said, ‘I’m trying to get them used to the language.’ ”

Johnson’s recollection tracks with the oft-told story of how Gregory had his wife call him the N-word so he, too, could get used to it, according to Chicago Tribune columnist Clarence Page.

“I felt like he was authentic,” says Chicago-based Diane Nash, a founding member of SNCC and an organizer of the 1961 Freedom Rides to desegregate interstate travel. “If he believed something, that’s what he did. He did come to Mississippi and demonstrate with us in the early ’60s, and he was obviously very insightful.”

George O’Hare, 90, remembers his good friend as “not just a showperson but a human being that really cared about things in the world.”

In the ’60s, O’Hare was a young sales executive with Sears Roebuck and Co. who liked using his expense account to visit local nightclubs. After seeing Gregory perform several nights in a row, Gregory struck up a conversation, and O’Hare ended up giving him a ride home in his used gray, two-door Ford Coupe with no back seat.

“I started driving him home every night,” O’Hare said. “In those days if you were white, you’d be in the passenger seat. I was driving the car, and he was in the passenger seat. People would slow down and look at us.”

O’Hare reveals that tapping the zeitgeist was actually the secret to Gregory’s sauce: “He was comedy from when he woke up till he went to bed at night. He would buy all the newspapers and magazines and go home and read them, and create jokes about the articles. So when he went into white nightclubs, it related to the white people.”

Gregory is inadvertently responsible for desegregating the record aisles at Sears, O’Hare said. When Memphis-based Stax Records sought to sell records featuring black singers there, O’Hare says he hesitated even though he knew whites loved the likes of King Oliver and Cab Calloway. Back then, good artists would sell no matter what color they were, but as soon as a picture of a black person appeared on an album, “all of a sudden they said don’t bring them in our stores,” O’Hare explains.

He brought the idea up to his friend Gregory, who pushed back: “What do you mean, ‘should you?’ ”

“The music business changed because Dick Gregory told me to put black artists in Sears on the end caps on the aisle so you could see they’re black,” says O’Hare, noting that record sales in his 34-store Chicago region went from $3 million to $38 million in a single year.

Though Gregory wasn’t an elected leader of the various local causes he supported, “People followed Dick because of the character he was,” Black says.

The manner in which Gregory would leverage serious issues in the service of comedy and vice versa was uplifting, Black says: “He was not the chosen leader, but he was a leader because he was inspirational.”

A celebration of Dick Gregory’s life will be open to the public on Saturday, Sept. 16, 2017, at City of Praise Family Ministries in Landover, Md. For details, visit: 

Deborah Douglas is an award-winning journalist who teaches at Northwestern University. She can be reached at or on Twitter at @deadlinedd.

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