Chelsea Handler's New Netflix Special Proves She Still Doesn't Understand White Privilege

In an alternate universe, Chelsea Handler could have been canceled a handful of times. It could have happened when she said three-year-old Pax Jolie-Pitt, who was born in Vietnam, would grow up to be a "horrible driver" and "amazing at nails." She could have gotten in trouble for the way she hyper-sexualizes Black men, as she did when she called Rick Ross "Chocolate Thunder" and "Black Magic" while straddling him at the 2010 MTV Video Music Awards. The final straw could have come in 2014 when she titled her book Uganda Be Kidding Me and had her co-star Chuy Bravo dress as Hitler to celebrate Germany's World Cup victory.

Instead, the book became her fourth New York Times bestseller. And though Chelsea Lately, her late-night comedy show, was canceled by E!, it wasn’t because of her Nazi joke, which happened two months after the cancellation. In the five years since the thoughtless book title and Hitler reference, Handler has inked lucrative deals with Netflix and NBCUniversal and written another bestselling book. In other words, she seems to keep getting a pass. Last week, in an interview with Jimmy Kimmel about her new Netflix documentary, Hello, Privilege. It's Me, Chelsea, Handler revealed she was forced to take sexual harassment training after she grabbed a Black woman's butt while the crew was filming a spoken word night for minority students at the University of Southern California.

Even here, she managed to dismiss her predatory behavior by turning it into a joke about being handsy—honking people's breasts or tapping somebody on their "Pikachu"—a sleight-of-hand one can only chalk up to her white, female privilege. Kimmel laughs (somewhat nervously) while listening to Handler recount this, but if Handler were a man, one can assume his response would have been much more grave. It's clearly a privilege to be Chelsea Handler because, despite numerous cancellable insults and other instances of inappropriate behavior, she doesn't seem to be going anywhere any time soon. On the surface, that's what makes her new documentary an interesting proposition: For the first time in her career, she seems to be willing to ask why she gets to stick around.

"I was white, I was pretty, and I had a big mouth and for some reason, that was rewarded in Hollywood," she says of her rise in the beginning of the new documentary. Handler's reputation on race is spotty, and following previous attempts to address that through comedy—such as in 2016’s tone-deaf Chelsea Does Racism—she seems to be trying on a new approach. The 64-minute Hello, Privilege takes a more somber approach with significantly less humor than its predecessor. Handler is taking a closer look at the ways her whiteness contributes to an otherwise sloppy sketch of race in America. It’s as though she’s finally ready to have tough conversations without hiding behind the tasteless jokes.

"I'm clearly the beneficiary of white privilege, and I want to know what my responsibility is moving forward in the world that we live in today where race is concerned," she says in the opening. Handler is in pursuit of a post-racial society: "I want to know how to be a better white person to people of color without making it a thing." Except, white privilege has always been a thing.

White privilege isn’t merely another social media buzzword in an internet culture obsessed with being "woke"; it is a descendant of centuries of racism and structural oppression, one that continues to predetermine America’s "winners" and "losers." For its benefactors, it's an uncomfortable phrase, one that forces an analysis of whiteness as something other than just the "norm"—and that is frequently dismissed on the erroneous basis that "privilege" is something reserved for the wealthy. In reality, there are multitudes of daily invisible acts that count as white privilege, from the "for normal hair" label on a shampoo bottle to not fearing for your life while engaging with the police.

"White privilege is one of those invisible things that white people are acculturated not to notice, because if we notice them, we might be responsible for addressing them," said Dr. Laura Smith, professor of psychology and education at Columbia University's Teachers College. "It's the whole portfolio of advantages, opportunities, civic protections, and open doors[…] that accrue to you because of your skin color privilege. It's also a portfolio of absences—the absence of violence and discrimination in your life—that you can look the other way and avoid commenting on directly. That's how the whole thing rolls along to another generation. You don't mention it if you see it."

For a long time, Handler didn't seem to see it. In Chelsea Does Racism, she boasted about her "egalitarian" approach to jokes, deeming it "almost racist not to" poke fun at stereotypes targeted at all races. Much of the 2016 documentary shows Handler in elegant dinners and therapy sessions, making the discussion about herself. Instead of seeking to understand the origins behind the stereotypes, it became about finding out what she was "allowed" to say. "Political correctness is the handicap of any real conversation and I hate it," she said in that film, echoing a common refrain among white comics whose words offend.

Chelsea Does Racism's most compelling moments arrive when she leaves Los Angeles and decamps for the South, in a seeming attempt to take the temperature on people's attitudes on race generations after slavery. At a historical plantation museum in Charleston, SC, Handler asks white residents their opinion on that history. One says, "People were taken care of"; another suggests that slaves and slave owners “were just all a big family." While in Charleston, Handler also visits the family of Walter Scott, an unarmed Black man who was killed in 2015 after a traffic stop, two weeks before Dylann Roof opened fire at Emanuel African Methodist Episcopal Church, killing nine Black churchgoers. "Negroes have lower IQs, lower impulse control, and higher testosterone levels in general," he wrote in his manifesto. "These three things alone are a recipe for violent behavior." The murder of the Charleston 9 only gets a brief mention on a title card in Handler's docuseries, but it is a piercing reminder that perpetuating stereotypes isn't harmless. It can have deadly repercussions.

If Chelsea Does Racism was the comic's way of dipping her toe in the pool of race relations, Hello, Privilege sees her braving the deep end without floaties. The beginning of the film finds Handler at the aforementioned open mic night, which was started for minority students by Jody Armour, a law professor at the University of Southern California. That night, the topic is white privilege, and Chelsea captures people sharing their thoughts. One audience member says the solution is "deeper than a documentary," while another points to the irony of Handler’s project. "Feel free to edit this out, because I'm embarrassed to be here with you because this is just another example of white privilege," she says. "What are you going to do with it other than come into this space and take?"

When it comes to dismantling racism, people of color are too often cast as both the tortured and the teacher. With Hello, Privilege, Handler seems to realize that the burden of that work should fall on white people. "We need to talk to people who are white and stop asking Black people to solve our problems because it's a white person's problem," Handler says when she returns to her car, sitting just a few feet away from Billy, her Black driver.

Much of Hello, Privilege exposes how invisible white privilege is to white people. A young woman says, "It's not something [she] sees very often," to which Handler asks: "But would you see it if you're white?"

When the comedian interviews a group of Republican women from Orange County, one of them uses air quotes when talking about "the white privilege thing." Others say they are more concerned about "Black privilege" granting people space in colleges and workplaces, even though studies show that in areas like education and hiring, white women benefit more than any other group from affirmative action. Like many other white people, on both sides of the political spectrum, they seemed to ascribe to the myth of equal opportunity: the idea that everyone is afforded the same chance at life.

To understand how deeply flawed that myth is, we need look no further than an anecdote Handler shares about own life during the film, about her former boyfriend, Tyshawn. "We got caught three times with dime bags," she said on Jimmy Kimmel Live! "Each time he was arrested and each time they told me to go back to my neighborhood." The two dated and Handler was even pregnant with his child when she was 16 until her parents decided she would have an abortion. Despite nearly failing out of high school, Handler transferred to an alternative school and graduated on time. Tyshawn matriculated through the prison system. In Hello, Privilege, Handler travels to his childhood home in New Jersey to see him for the first time in 25 years. He's adjusting to life after spending 14 years in prison for armed robbery.

"At that time, that was just the thing I had to do—or I felt I had to do," Tyshawn tells Handler about his choice to sell drugs in high school. His mother speaks candidly about the addiction issues she struggled with while raising her son. "I was mad at my mom because she married a Black man that gave me knotty hair and dark skin," she says. As Tyshawn grew older, they struggled to get along. "He was blaming everything on me, like I was blaming everything on [my mom]. It was just a vicious cycle." Tyshawn's mother had dreams for her son to become a professional football player, dreams the "cycle" didn't allow. "He was on his way," she says. "He had scholarships and everything. He took the wrong turn."

By the end of Hello, Privilege, Handler seems more mature than the woman who once asked Al Sharpton why she couldn't joke about fried chicken and watermelon. But the story about her grabbing a woman’s butt begs the question of what her activism looks like when the cameras aren't rolling. Chelsea Does Racism and Hello, Privilege may be respectable first steps, but they aren't enough to excuse Handler's past and present behavior. Being a white ally to people of color goes beyond the proverbial "invite to the cookout." And dismantling white privilege shouldn't come at the cost of the people of color around you.

After all, as Dr. Smith reminds us, “You can process your feelings about what's hard about it with white people, not the people of color in your life. They're exhausted. They're trying to survive." It’s a truth that Handler seems to be beginning to come to terms with, perhaps without realizing that on more levels than one, she needs a doc like Hello, Privilege much more than any of the people of color she interviews. "One of the parts about being a white ally,” Dr. Smith says, “is realizing that every single thing that you have to say about racism, all the people of color you know already thought of it a long time ago, and they've lived it out.”

Kristin Corry is a staff writer for VICE.