Stream It Or Skip It: ‘Milestone Generations’ on HBO Max, a Documentary About Groundbreaking Black Representation in Comic Books

Now on HBO Max, Milestone Generations is an hourlong documentary chronicling the all-too-brief history of Milestone Media, the first-ever comics company owned by Black artists and telling the stories of Black characters. The company enjoyed a four-year run in the 1990s thanks to a publishing deal with DC, who produces this potentially revelatory reminder that a handful of writers, artists and businesspeople were ahead of their time in the push for cultural representation.

MILESTONE GENERATIONS: STREAM IT OR SKIP IT?

The Gist: Cliff Smith – better known as Method Man – sits behind the teacher’s desk in a staged classroom, talking about comic books. (Side note: I WOULD LIKE TO TAKE THAT CLASS, PLEASE.) Historically, the vast, vast majority of the medium’s creators were white males writing and drawing the adventures of white heroes. It was that way for decades, until the needle started to move in the 1970s with DC’s Black Lightning hero, who voice actor Phil LaMarr appreciated because his afro was attached to his mask, not his head. LaMarr amuses himself by impersonating how he imagines Black Lightning talks with his afro on, and with his afro off.

Around the time of that character’s funnybook debut, Denys Cowan was a young teen who started reading comics, and dreaming about making them. By the early 1980s, he was part of the DC stable (and also Marvel, but that’s glossed over here), and made a name for himself drawing The Question. He plugged away, splitting time between white crusaders like Batman and the Flash, and the occasional Black hero, like Dethlok and… Prince? Yes, Prince, the musician and one-time-only subject of a DC comic.

Method shifts to Black history when talking about the explosive crossover of Black culture in the early 1990s: Hip-hop, sports superstars, In Living Color. In 1992, Cowan was wandering through a comic convention, pondering the marked lack of people who looked like him drawing and starring in comics, when he spawned an idea to create his own company consisting of Black creators telling stories about Black characters. He gathered Michael Davis, Dwayne McDuffie and Derek T. Dingle as partners, and they founded Milestone Media. And get this – they retained ownership rights to their characters when they got DC to publish and distribute their books.

So POW! And WHAPPO! They came up with Blood Syndicate and characters like Static, Icon and Hardware, all representing Black culture. No detail was spared – the books were a little more expensive than others because of a complex coloring system that allowed them to show a diverse variety of Black skin tones. The doc is a little smudgy on the numbers, but Cowan and the like all attest to the books’ solid sales stats – and yet, they didn’t get the respect they deserved from retail establishments and DC higher-ups who thought all-Black superhero comics would never appeal to non-Black readers. Clashes and divisions ensued. By 1997, Milestone comics ceased making books, although Static found new life in an animated TV series, Static Shock. The project was great while it lasted, and was looked upon fondly by its creators. Until 2020, when Milestone was reborn, as comics (available now!) from some founding artists as well as a bevy of new ones for the sometimes turbulent current times. There’s also big plans for movies and animation. Hooray for franchises!

What Movies Will It Remind You Of?: Well, it’s not Crumb. Not at all. It brings to mind Enter the Anime, a doc about anime that isn’t really about anime itself, but a specific streaming company’s anime offerings, and isn’t really a doc, but a glorified promo reel.

Performance Worth Watching: LaMarr is the funnyguy who can also put the subject matter into proper context. But Cowan is the doc’s consistent, steady presence, the man who tells the story of Milestone with earnest conviction.

Memorable Dialogue: Opening narration: “When you’re a kid, you’re really focused on just drawing comic books. You’re not thinking about, ‘I’m a Black comic book artist. I’m gonna change the industry’… the only thing that matters is what you’re trying to do. Bring that thing that you wanna do into existence, no matter what.”

Sex and Skin: None.

Our Take: Being a DC-produced documentary about a DC property, Milestone Generations gives off a lot of promo-fluff vibes, bridging the gap between historical retrospective and soft-serve marketing. It maintains a serious tone with playful notes as it gently addresses systemic racism in the comics biz without sinking its teeth too deep into heavier content. It doesn’t name names, because DC in 2022 doesn’t want to make DC in the mid-1990s (or the ’80s or the ’60s or…) look too bad.

But I also think the Milestone story will be revelatory for people who weren’t deeply entrenched in 1990s comics culture. The works of Cowan and co. definitely flew under the radar, partly due to discriminatory attitudes, and partly due to the decade’s major comics-biz glut (it was a time when many creators successfully fought to retain commercial rights for their properties, and launched enough independent publishing houses to give Marvel and DC a run for their money). Hardware and Spark definitely didn’t get the marketing push that the work of big-name artists did. At the very least, some of us will be inspired to hunt down some back issues and enjoy the forward-thinking stories.

But this is also a story about people who were so far ahead of the cultural-progress curve, their innovation wasn’t appreciated until well after the Milestone offices were shuttered. The rebirth of Milestone is clearly the result of a recent push for broader representation in many entertainment mediums; Milestone Generations quietly asserts that this handful of Black men were doing it before anybody else.

Our Call: Milestone Generations is a worthy, potentially educational (and concise!) watch that highlights some unsung heroes of the comics field. STREAM IT.

John Serba is a freelance writer and film critic based in Grand Rapids, Michigan. Read more of his work at johnserbaatlarge.com.

Stream Milestone Generations on HBO Max