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Is Chelsea Handler’s exploration into white privilege worth the watch?

Comedian Chelsea Handler set out to create a documentary exploring her white privilege in an attempt to be a better ally to POC.

The intention is positive, but the documentary lacked a lot. Handler seemed to bite off more than she could chew. She did, however, make it clear that being Jewish does not exclude you from white privilege.

Handler begins by speaking to two Black comedians about what she’s setting out to do. She asks Tiffany Haddish and Kevin Hart to tell her the most important thing they’d like white people to know about white privilege.

A question that already limits the conversation and is inherently hard to answer. Chelsea’s learning right? Haddish makes an emotional speech about having a generational wealth of knowledge, power, and economic means.

But somehow Chelsea ends up somewhere making a joke about an old Jewish man dying in Tiffany’s arms during a Bat-mitzvah? Already not a great vibe.

Rocky start

Early in the documentary, Chelsea goes to a gathering of young people, primarily college students discussing white privilege through an open mic type forum.

After introducing herself and explaining why she’s there and asking to learn, several people of color had critiques to share. One woman, in particular, pointed out the privilege of even being able to make a documentary centering around Chelsea. And she’s right.

It’s ironic that making a self-reflecting documentary about white privilege is actually a privilege. Let’s not kid, this film will make money, Netflix money.

It will be a calling card of virtue for its star (even if that’s unintended by her). And as another attendee of the open mic expressed, a documentary talking about privilege won’t change things, action will.

Listening and learning falls short

Chelsea did listen though. As best she could in her journey through discovering whiteness, it was apparent that she was listening. She heard the frustrations of POC saying they’re tired of teaching white folk about their own issues with whiteness.

So, Chelsea changed course and sought out to talk to white people about privilege. And again, despite the intentions being positive, it had a surface-level impact.

The whites she talked to overwhelmingly downplayed or denied white privilege and Chelsea barely questioned them. The montage felt like a poorly executed correspondent package from the daily show because none of the hard-hitting questions or debating or redirecting consciousness was there.

But she tried again. This time with a group of female conservatives, most of which started out denying white privilege and later lightly considering the possibility of its existence.

This part of the film might have been the most beneficial.

In too deep

During her conversations with white Tennessee rapper Jelly Roll, Chelsea realized something about her privilege. While in high school she had a black boyfriend who frequently got into trouble related to drug possession while she got off easy.

The realization was a cringe-worthy watch. It was important for her exploration of white privilege but seeing it again in a documentary on Netflix felt sus.

It could be the idea that Chelsea is making money off of her journey to wokeness and that she’s gaining social status off of her realization that she has the privilege. But her next step was particularly jarring.

She went to visit said ex-boyfriend to share her realization. But the conversation was more about how he ended up in jail for 14 years, a story he said he didn’t want to talk about, but Chelsea persisted. The meeting with his mom and talking about their drug addiction just felt wrong after that.

The takeaway

The big takeaway from the documentary that was reiterated by several of the people interviewed was that white people need to have the difficult conversations about whiteness with each other and be allies 24/7 not whenever they feel guilty.

The truth is, every white person’s journey into realizing their racial privilege and working on being an ally is different. It takes time, it takes mistakes. Chelsea’s mistakes aren’t the issue, so much so as the televising of those actions as heroic feats.

Don’t watch this thinking it will have a revolutionary impact on how white America views its own privilege. Watch the 13th again instead if you’re looking for that kind of life-changing knowledge.