Don Rickles called out the five most disgusting racist stars in old Hollywood Golden Age history. For 60 years, Don Rickles walked onto stages from the Sahara to the Sands to the Tonight Show to the Oval Office, and across those six decades, he built a career on a single revolutionary premise.
The premise that nobody in the room was safe from his tongue. No matter how famous, no matter how powerful, no matter how protected by the carefully maintained images their publicists had spent millions of dollars constructing. Frank Sinatra heard Rickles insult him to his face and survived the experience.
Presidents endured the same treatment. Every star who ever set foot in Las Vegas felt the same heat. Johnny Carson famously nicknamed him Mr. Warmth, a joke so dark that it turned into one of the most affectionate titles in American entertainment history because everyone in show business understood that nobody on the planet was less warm than Don Rickles when the lights came up and the microphone went hot.
What separated Rickles from every other insult comedian of his generation, and what made his approach to comedy genuinely revolutionary, was the way he handled race. The Jewish kid from Queens deployed racial stereotypes as a way to expose them. Performed bits that put the audiences own discomfort on display, and built personal friendships with Sammy Davis Jr.
and Sidney Poitier and dozens of other black performers who genuinely loved him because his humor punched at racism rather than at the people racism targeted. Black entertainers knew Rickles stood on their side, and that fact uniquely positioned him to observe the people in Hollywood and Las Vegas who did not. A close colleague who worked with Rickles across multiple decades recalled that Don remembered every slight, every cruelty, every moment he watched a black colleague humiliated by a system designed to extract their talent while
denying their humanity. The memories accumulated across his 60 years in entertainment, from his earliest days in the Catskills through the Vegas explosion of the 1960s into his Tonight Show appearances and his late career in films like Casino and Toy Story, and Rickles carried those memories the way other comedians carried their best material, ready for deployment when the moment was right.
When he published his memoir, Rickles’ Book, in 2007, that moment finally arrived. Rickles wrote about the contemporaries he had loved, the friends he had buried, and the racists he had despised, and the candor of those passages startled the entertainment journalists who had assumed Rickles would soften with age the way most comedians do. He did not soften.
He named names, told stories, exposed contradictions, and made clear that the gentleness he showed his friends had nothing in common with the contempt he carried for the people who had treated those friends as less than human. Most disgusting among the stars Rickles called out across his career and his memoir were the Hollywood titan who used his position to build the institutional machinery that destroyed black performers’ opportunities for decades.
The eccentric billionaire whose obsessive control over his studios extended into racial policies that shaped what generations of Americans saw on screen. The casino executive who forced one of America’s greatest entertainers to exit through the kitchen after performing for thousands of white people in the same building.
The manager who built the biggest career in American music history on black sounds while keeping the actual black artists invisible. And the entertainer whose entire fortune came from painting his skin dark to mock black people for white audiences who paid record prices to laugh at the caricature. These were not subtle racists. These were not the secretly compromised stars whose contradictions required documentation and explanation.
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The five figures Rickles named represented the people everyone in entertainment knew were poison. The ones the industry protected because their power or their box office or their political connections made the protection worthwhile. And according to Don Rickles, what they did to his friends and to the colleagues he respected made them deserving of every harsh word he ever spoke about them.
These are the five most disgusting racist stars in old Hollywood Golden Age history Don Rickles called out across his 60 years in entertainment. The ones whose names made him visibly angry in interviews until the day he died in 2017. Starting with number five. Number five. Cecil B. DeMille, the founding father of Hollywood.
Few names in the history of American cinema carried more institutional weight than Cecil B. DeMille. Because DeMille had been there at the beginning, directing Hollywood’s first feature-length film in 1914, building the visual language of the biblical epic across The Ten Commandments and Samson and Delilah and King of Kings, and establishing himself across five decades as the most powerful director Hollywood had ever produced.
The inaugural Cecil B. DeMille Award for lifetime achievement Golden Globes in 1952 carried his name, an award still given in his name to this day. The Hollywood Walk of Fame, the Directors Guild, the entire institutional apparatus of American cinema carried DeMille’s fingerprints, and his death in 1959 turned him into the kind of figure no working filmmaker dared criticize publicly.
Don Rickles was just emerging in Vegas when DeMille died, but every comedian and every performer who came up in entertainment during the 1950s knew the stories about who DeMille had actually been when the cameras stopped rolling on his productions. The myth of DeMille as the genteel patriarch of American cinema, the dignified man in jodhpurs barking orders from his director’s chair, concealed a documented history of using his enormous institutional power to build the machinery that would devastate black
performers and progressive performers across two decades of Hollywood history. Co-founding the Motion Picture Alliance for the Preservation of American ideals in 1944 placed DeMille alongside John Wayne, Hedda Hopper, Adolphe Menjou, Ward Bond, and other figures who would spend the next decade enforcing the Hollywood blacklist.
The alliance operated as the primary mechanism for identifying and destroying performers whose politics threatened the conservative vision DeMille and his colleagues envisioned for American entertainment. And the performers they targeted most aggressively included anyone who supported civil rights, attended integration meetings, or used their platforms to advocate for racial equality.
DeMille personally supplied the House Un-American Activities Committee with names, leads, and testimony the committee deployed to build cases against blacklisted performers, and the cases the committee built relied on the same racial logic the alliance had been promoting, the logic that progressive politics on race constituted evidence of communist sympathy worthy of professional destruction.
Public criticism came from the Anti-Defamation League over the alliance’s tactics and the anti-Semitic and racist undertones of its blacklist enforcement. But DeMille’s institutional power within Hollywood remained so vast that the criticism rolled off without consequence. What Rickles found particularly disgusting about DeMille was the public reverence that continued to surround his memory long after the documented evidence of his blacklist activities had emerged.
The Golden Globe still gave out a Cecil B. DeMille Award. Film schools still taught his productions as foundational works of American cinema. The director who had spent the final 15 years of his career building the institutional machinery that destroyed dozens of careers and shaped what an entire industry believed about racial politics received only celebration in the public memory, while the people his alliance had targeted often died in obscurity.
A close colleague recalled Rickles observing in a private conversation that DeMille produced movies about Moses leading his people out of bondage while spending his real life building a system designed to keep certain people in their bondage, and that no greater contradiction existed in the history of American cinema than the director who taught audiences about freedom from a position of building the most effective tools for taking freedom away from his colleagues.
Number four, Howard Hughes, the eccentric billionaire. For four decades Howard Hughes ranked as the most powerful and most peculiar figure in American business. The aviator who broke speed records, the billionaire who controlled RKO from 1948 to 1955, the eccentric who would eventually retire from public life into the obsessive isolation that defined his final two decades, and the man whose influence over Hollywood and Las Vegas reached into corners of the entertainment industry most observers
never fully understood. By the time Don Rickles was establishing himself as the king of Las Vegas insult comedy, Hughes had already begun his quiet acquisition of Vegas hotels and casinos that would eventually give him control over significant portions of the strip. Rickles performed in Hughes-controlled venues throughout the 1960s and into the 1970s.
And the racial policies Hughes enforced through his casino ownership directly shaped the experience of every black performer who worked the strip during those years. Hughes ran his Vegas properties on the same racial principles he had run RKO, which meant black performers could appear on the marquee, fill the showrooms, generate the revenue that built the city, while being forbidden from the hotel rooms, the restaurants, the swimming pools, and the front entrances of the buildings where their talent made
everyone else rich. The RKO years revealed Hughes’s approach to race in cinematic terms most clearly, because under his control the studio that had once produced films like Cabin in the Sky shifted away from any meaningful black representation, with Hughes personally vetoing projects that would have featured black performers in lead or equal status roles.
The studio’s black employees during his tenure documented the racial atmosphere he created, an atmosphere where their continued employment depended on accepting hierarchies other studios were beginning to dismantle. Hughes’s personal life provided additional context for his racial views, because his documented relationships and business dealings reflected the same selective exclusion that characterized his professional choices, with the eccentric billionaire surrounding himself with a small circle of trusted aids who shared his
racial assumptions and enforcing those assumptions across every business he touched. His control over Jane Russell’s career grew famous for its obsessive specificity, and the same control extended to dozens of other performers and crew members whose professional lives Hughes shaped according to standards that ranged from quirky to disturbing.
What Rickles witnessed in Vegas was the practical reality of Hughes’s racial policies translated into the daily humiliations black entertainers experienced at properties Hughes owned. Sammy Davis Jr. could pack the showroom at the Desert Inn which Hughes acquired in 1967 while being forced to navigate the same indignities that had defined black performers Vegas experience for decades.
The change in ownership at properties like the Desert Inn did not translate into meaningful change in racial practice because Hughes had no interest in dismantling systems that profited him. A former colleague recalled Rickles observing that Howard Hughes had enough money to buy whatever world he wanted and chose to use his fortune to keep the world exactly as small and exactly as white as it had always been for him and that the saddest part about Hughes was not his eccentricity, but the way the press treated his racism as
one more quirk in the catalog of weirdness that defined the great American billionaire. Number three, Jack Entratter, the Sands Hotel strongman. Of all the names Don Rickles called out across his 60 years in entertainment, no entry generated more sustained emotion in his interviews than Jack Entratter because the Entratter story involved Sammy Davis Jr.
directly and Davis was not just one of Rickles’ closest friends, but the brother he had chosen for himself in an industry that made interracial brotherhood enormously costly. Jack Entratter ran the Sands Hotel and Casino from 1952 until his death in 1971, presiding over the most glamorous showroom in Las Vegas during the years when the Rat Pack defined American entertainment and the Sands Copa Room hosted Frank Sinatra, Dean Martin, Sammy Davis Jr.
and the late-night Summit performances that became legend. Entratter was charming, well-connected, mob-affiliated, and powerful in ways that turned him untouchable within the Vegas hierarchy. Emerging from the Copacabana in New York, he brought with him the racial policies that had defined that venue. Policies he enforced at the Sands with the same iron consistency.
The Sands booked black performers because black performers sold tickets. Sammy Davis Jr. could pack the Copa Room every night of an engagement, drawing wealthy white audiences who paid premium prices to watch him sing and dance and tell jokes that crossed racial lines in ways nobody else in entertainment was attempting.
The audiences applauded, requested encores, and left convinced they had witnessed something genuinely progressive. What those audiences never saw, and what Jack Entratter enforced with absolute consistency, was the exit through the kitchen. After Davis finished his sets at the Sands, after the standing ovations and the encore performances, he could not walk through the lobby of the hotel where he had just headlined.
The casino entrance remained off-limits. The restaurants where his fans were dining. The hotel rooms where they were staying. All of it stayed closed to him. Entratter required Davis to exit through the kitchen, navigate the service corridors, and find his way to the segregated boarding houses on the west side of Las Vegas where black performers were required to lodge regardless of their fame or their fees.
The policy was no casual oversight or remnant of a less enlightened era Entratter had failed to update. The policy was a deliberate enforcement of racial hierarchy Entratter maintained personally, with documented confrontations between him and performers who tried to challenge it. When Sammy Davis Jr. attempted to use the front entrance during one of his early engagements, Entratter reportedly told him directly that his contract did not include lobby privileges, and that if Davis wanted to continue performing at the Sands, he
would continue using the back doors like every other black performer who had ever worked the venue. Don Rickles witnessed the policy firsthand throughout the 1960s because Rickles performed at the Sands during the same years Davis was headlining, and the two men became close during exactly the period when Entratter’s racial enforcement was at its most aggressive.
Rickles saw his friend exit through kitchens night after night while audiences cheered for him from the showrooms he had just filled. Rickles heard Davis describe the indignities of the boarding houses, the navigation of service corridors, the small daily reminders that no amount of talent or fame could buy a black performer access to the same air the white audience breathed.
Rickles wrote about the Sands era in his memoir with controlled fury, naming Entratter directly and describing the policies in clinical detail because he wanted readers to understand exactly what one of America’s greatest entertainers had endured at the hands of a casino executive who lived comfortably on the revenue Davis’s performances generated.
The kitchen exit was neither metaphor nor exaggeration. The literal architecture of Las Vegas racial policy in the 1950s and 1960s came down to physical doors and service corridors enforced by men like Jack Entratter who profited enormously from the talent they were refused to treat as fully human. A close colleague recalled Rickles becoming visibly angry whenever the Entratter name came up in conversation late in his life, telling friends that Sammy Davis Jr.
had been the greatest entertainer who ever lived, and that men like Jack Entratter had spent two decades making him use the back door of the buildings where his talent paid the salaries of every white person inside, and that some chapters of Vegas history were not nostalgia or romance, but documented cruelty disguised as showroom glamour.
Number two, Colonel Tom Parker, the manager who built Elvis. For two decades, Colonel Tom Parker controlled the most valuable career in American entertainment, managing Elvis Presley from 1956 until Elvis’s death in 1977, building the King of rock and roll into a global phenomenon while taking 50% of his client’s earnings and shaping every major business decision of Elvis’s career.
Parker was Dutch-born, traveling carnival background, fake military title, and possessed of a business cunning that turned Elvis Presley into the most commercially successful solo performer in the history of recorded music. Don Rickles knew Parker through the Vegas years because Elvis’s Vegas residency from 1969 onward overlapped extensively with Rickles’ own Vegas dominance, and the two men encountered each other repeatedly at the International Hotel and at the industry gatherings that defined Vegas in the 1970s. What Rickles observed about
Parker, and what eventually emerged through years of documentation and the testimony of musicians and industry insiders who watched the Parker operation up close, was that the entire commercial empire Parker built around Elvis was structured to profit from black music while keeping black artists invisible and uncompensated.
Elvis Presley grew up immersed in black music, attended black church services in Tupelo and Memphis, learned his vocal style from the gospel and rhythm and blues traditions that defined southern black culture, and recorded his earliest hits as direct interpretations of songs originally created by black artists.
“That’s All Right, Mama”, the song that launched his career, was an Arthur Crudup composition. “Hound Dog” originated as a Big Mama Thornton recording. The musical vocabulary Elvis brought to mainstream white American audiences came from black vocabulary, learned and absorbed and translated for a market that would never have bought the originals.
Parker structured the business around that translation with deliberate calculation. The original black artists whose songs Elvis was recording received minimal compensation, often having signed away their rights for token sums in the racially exploitive recording contracts that defined the 1950s music industry. Parker negotiated Elvis’ deals with full knowledge of the racial economics involved, and he made no effort across two decades to advocate for the original artists or to ensure that Elvis’s enormous platform was used to spotlight
the black musicians whose work had made his career possible. The international tours Parker refused to book for Elvis remained one of the most peculiar features of his management, and the standard explanation involving Parker’s undocumented immigration status held up under scrutiny only partially because the deeper truth involved Parker’s calculations about the racial dynamics of international audiences.
European audiences who knew the original black artists Elvis was covering might have asked uncomfortable questions about the racial economics of his career, and Parker preferred to keep Elvis insulated from the international scrutiny that would have raised those questions. What Rickles understood about Parker, and what he eventually documented in conversations with musicians and entertainment journalists, was that the Parker operation represented the most successful financial extraction of black creativity in American music history.
Parker took 50% of Elvis’s earnings. Elvis took the lion’s share of what remained, and the black artists whose musical innovations had made the entire empire possible received fractions of pennies on the dollar, while Parker’s compound and Elvis’s Graceland filled with the wealth that black creativity had generated.
A former producer recalled Rickles observing in a private conversation that Colonel Tom Parker built the biggest career in American music history on stolen sounds, and made sure the people he stole from never got close enough to be photographed in the same frame, and that the genius of Parker’s racism was that it operated entirely through contracts and bookings and business decisions, leaving no public record of bigotry while extracting more wealth from black music than any single white man in the
history of American entertainment. Number one, Al Jolson. The most disgusting performer in American entertainment history. There was no entry on Don Rickles’ list more foundational to the entire history of racism in American entertainment than Al Jolson. Because Jolson had not merely participated in blackface performances one element of his career, but had built his entire fame, his entire fortune, his entire historical legacy on the systematic mockery of black identity for white audiences. Every major
performer who ever painted their skin dark to entertain a white crowd was working in a tradition Jolson had defined and perfected. And the cultural damage of that tradition extended across nearly a century of American popular entertainment. Born in 1886 in what is now Lithuania, Jolson emerged in vaudeville in the early 1900s and quickly turned into the highest-paid entertainer in America, performing in blackface across Broadway and the touring circuits while developing the exaggerated mannerisms, the dialect, the
rolling eyes, and the kneeling delivery that would become the visual language of blackface for decades. His 1927 film The Jazz Singer, the first feature-length motion picture with synchronized sound, turned Jolson into the most famous performer in the world and embedded blackface performance permanently into the foundation of American cinema because the film that launched the talking picture era featured Jolson in extended blackface sequences the studio marketed as the film’s emotional centerpiece. Don
Rickles came up in Catskills and vaudeville traditions that were still digesting Jolson’s enormous influence when Rickles was a young comedian in the 1950s. And what Rickles understood about Jolson, and what he eventually said about him in interviews late in his career, was that Jolson represented the original sin of American entertainment racism, the foundational performer whose work had legitimized blackface as mainstream commercial entertainment and made it possible for every subsequent star from Eddie Cantor to Mickey Rooney
to Judy Garland to participate in the same tradition without facing immediate cultural reckoning. What separated Jolson from later blackface performers, and what made his case particularly disgusting in retrospect, was the totality of his commitment to the form. Other performers who deployed blackface across the 1920s, 1930s, and 1940s treated it as one technique among many in their performance toolkits.
Jolson treated it as the core of his artistic identity, performing in blackface across thousands of performances, recording dozens of songs in the blackface vocal style, and using his enormous cultural authority to defend the practice publicly throughout his career as legitimate American entertainment.
The defenders of Jolson’s legacy across the decades since his 1950 death have argued repeatedly that he held genuine personal affection for black performers, occasionally championed black artists privately, and represented a complicated rather than straightforwardly racist figure in American cultural history. The arguments contained partial truths.
Jolson did help certain black performers professionally. He did express what he considered admiration for black musical traditions. He did break some industry color lines in limited ways. None of those mitigating facts address the central problem of Jolson’s career, which was that he built the most successful entertainment business in American history on the premise that white audiences would pay extraordinary sums to watch a white man paint his skin dark and mock the identity of the people whose musical traditions he was
simultaneously borrowing from. The contradiction was neither subtle nor accidental, but central to the commercial proposition of Jolson’s entire career. And the success of that proposition shaped what American audiences expected from popular entertainment for the next 40 years. What Rickles found particularly disgusting about Jolson was the cultural laundering that followed his death because the 1946 biographical film The Jolson Story and its 1949 sequel Jolson Sings Again presented Jolson as a sympathetic American success story while
minimizing or romanticizing the blackface that had defined his career, and generations of American film goers learned to remember Jolson as a beloved entertainer rather than as the foundational architect of mainstream blackface performance. The institutional memory of American entertainment continued treating Jolson as a complicated figure deserving of nuanced appreciation, while the cultural damage his career had caused continued shaping how American audiences understood race and performance. A close colleague
recalled Rickles observing late in his life that every comedian and every musician and every performer who ever participated in racial mockery for laughs was working in the tradition Al Jolson built and that the disgusting thing about Jolson was not just what he personally did across his decades of blackface performance, but what his enormous commercial success made possible for everyone who followed him because Jolson proved that white audiences would pay premium prices to watch black identity reduced to
caricature. And that proof became the business model for an entire generation of American entertainment. What Don Rickles called out across 60 years, 60 years Don Rickles spent inside the entertainment industry performing alongside the men who shaped American show business watching them up close at the casinos and the studios and the late night gatherings where the biggest names in entertainment crossed paths with each other repeatedly across the decades.
What he witnessed across those six decades was the gap between who American audiences believed these stars to be and who they actually were when the lights came down and the kitchen doors opened and the performers who had filled the showrooms were sent back to the segregated boarding houses where their fame did not protect them. Five names.
The Hollywood founding father who built the institutional machinery that destroyed dozens of careers and shaped what an entire industry believed about racial politics for decades. The eccentric billionaire whose obsessive control over his studios and his Vegas casinos translated into racial policies that humiliated black performers across every property he owned.
The casino executive who forced Sammy Davis Jr. to exit through the kitchen after performing for thousands of white people in the same building. The manager who built the biggest career in American music history on black sounds while making sure the actual black artists who created those sounds remained invisible and uncompensated.
The entertainer whose entire fortune came from painting his skin dark to mock black identity for white audiences who paid record prices to laugh at the caricature. Rickles called all of them out across his 60 years in entertainment. He named them in his 2007 memoir. He named them in his interviews.
He named them in the late-night conversations with comedians who would eventually become the next generation of insult comics carrying forward his tradition. The reason he called them out was simple. Rickles believed that comedy could expose racism only if comedians had the courage to identify racists by name.
And the names he carried for decades belonged to the people who had hurt his friends most directly. What separated Rickles from the other Vegas comedians of his generation was his willingness to remain angry across six decades. His refusal to let the comfortable amnesia of nostalgia rewrite what he had personally witnessed, and his insistence that the people who had built their fortunes on racial cruelty be remembered for the cruelty rather than the fortune.
Rickles named names. He wrote about hypocrisy. He gave interviews until he was almost 90 years old in which he refused to soften his judgments about the men who had treated his friends like property. The cameras showed America one version of these five icons, and Don Rickles called out another version entirely.
And what he witnessed across 60 years was that the most institutionally protected reputations in American entertainment were almost always the ones built on the most direct racial damage, that the men who shaped the industry’s public memory were sometimes the men whose private behavior had done the most harm to the people who could least afford to be harmed, and that the only way to make the lie stop was for someone who had been in the room to finally point at the people who had built the room and tell the truth out loud about what they had been doing
inside it. Which revelation shocked you most? Did you know about these documented accounts before today? Share your thoughts in the comments below. And if you found this exploration of Hollywood’s hidden history valuable, do not forget to like and subscribe for more untold stories from entertainment’s complicated past.
