While shock jock humor is the brand that made Howard Stern famous, an interview on Magic Johnson’s 1998 late-night talk show “The Magic Hour” pushed the limits even for him, creating one of the most uncomfortable moments in late-night TV history.

In a new interview with Variety, Johnson looked back on his hosting stint prior to the April 22 release of “They Call Me Magic,” an Apple TV Plus docuseries that covers his life and career — including his brief chapter in the late-night seat. And though “The Magic Hour” was an overall flop, hated by critics and canceled after three short months, it’s Stern’s appearance on the program that still gets talked about today as a blatant example of how entertainers could get away with making racist comments before things changed in our culture.

“So many times, I wanted to say something and hit him at the same time — on air,...