We take black mega-celebrity endorsers as a given today: Michael Jordan, Oprah Winfrey, Beyonce, the husk that was once Tiger Woods. They wield a kind of agency that seems to continually reset the upper limits of black aspiration, while remaining more or less incidental to the median black condition.

It wasn’t always so. There was a moment in the 1960s, for example, when the Supremes were one of the biggest acts in show business, with a string of Top 10 hits. But the trio weren’t making a lot of money endorsing products made by big companies — or, at least, not endorsing those products to “mainstream” (read: white) audiences.

According to Tom Burrell, the pioneering ad executive and the subject of the latest Code Switch podcast, Coca-Cola would only placed ads featuring the Supremes on black radio, so worried was the soft drink giant that the trio might scandalize white consumers

That line of reasoning held sway for a long time, until people like Tom Burrell helped dislodge it. Burrell one of the very first black men in advertising, and his hire for a job in an agency’s mailroom was considered so risky that the company’s CEO had to be called in from vacation to sign off on it. And because Burrell was a black man climbing the corporate ladder in the 1960s, he saw his work as part of a larger project. Burrell understood, too, that he wasn’t just selling burgers for McDonald’s, but politics: His ad campaigns were always informed by his belief that they should portray black folks in the most affirming light.

Today we call this “respectability politics,” the practice of using “positive” portrayals to counter unflattering stereotypes as a way to further racial equality. There are lots of valid critiques of this line of thought — is discrimination against black people who are less “respectable” somehow more justified? — but it was in step with the mores held by many folks of that era. It’s the reason so many images of the civil rights movement show protesters in dresses and crisp shirts and ties — their appearances beyond reproach. It was a media play, by activists, for the hearts and minds of the broader public.

Sonari Glinton, a business correspondent at NPR, brought us Burrell’s story. He says Burrell changed how advertisers thought about who they could sell to, and who their audiences might buy from. Burrell’s agency found that white audiences responded more positively to ads with black actors and celebrities targeted to black people than they did to ads aimed at white consumers. (Make of the implications there what you will.)

As Sonari and I talked, we couldn’t help but note the odd coincidence that the first shining exemplars of the crossover black pitchman — O.J. Simpson and Bill Cosby — are today seen by an awful lot of folks as supervillains. “O.J. was the first to demonstrate that white folks would buy stuff based on a black endorsement — as long as it was not pressed as a black endorsement,” said Harry Edwards, a sociologist at the University of California, Berkeley, during the Oscar-winning documentary, O.J.: Made In America.

A key to understanding the robust support those two men still enjoy in some places is remembering that their particular celebrity always carried a different gravity than that of their white contemporaries — regardless of whether they personally leaned into it. Simpson famously avoided speaking out on racial issues, and Ezra Edelman, the director of OJ: Made in America, told us last fall that those famous Hertz commercials featuring Simpson were cast so that he was the only black person in them. It was never just Pudding Pops, then, but politics: Simpson and Cosby became famous when being black and on America’s TV sets was still a novel and subversive notion, even a dangerous one.

That doesn’t, and shouldn’t, make those men any more sympathetic. But it might shed light on the people who still vocally defend them; they were not only selling products but a seductive vision of a black America not weighted down by American racism. A black celebrity accused of the same crimes but who rose to prominence at a later time — a time with different politics around race and gender — might not enjoy the same tortured benefit of the doubt. (When Burrell, a generational contemporary of those two, was asked in 2014 what he made of the avalanche of sexual assault accusations against Cosby, he offered up a politician’s non-statement: “It’s sad if it’s true, and it’s sad if it’s not.“)

The squeamishness about black pitchmen as the face of “mainstream” ad campaigns lingered even after Burrell (and yes, Cosby and Simpson) terraformed the marketing landscape. Decades after the Supremes’ heyday, in the Cola wars of the 1980s, Coca-Cola offered Michael Jackson — by then, on his way to becoming the biggest and most ubiquitous celebrity in the world — a $1-million dollar endorsement deal. But it envisioned a “targeted, ethnic campaign,” recalled Jay Coleman, a businessman involved in the negotiations, told Billboard in 2009.

Jackson passed, and instead, inked a then-record endorsement deal with the competition: Pepsi. That deal spawned Pepsi’s inescapable “New Generation” campaign that ran for nearly a decade on primetime network TV; Pepsi’s sales and market share climbed. Meanwhile, Coke’s position fell, all while being implicitly cast as the preferred soft drink of out-of-touch fogeys and not the “new generation.”

The campaign also served as an inflection point, the moment in which it became clear that corporations might benefit more from their proximity to a black star than the other way around. And it also, perhaps, presaged the world on the horizon, where the influence of those stars would become at once more pronounced and less inherently charged. America has gotten pretty used to ubiquitous black celebrity, even as it’s still trying to figure out what to make of black folks, broadly.

Copyright 2017 NPR. To see more, visit http://www.npr.org/.