I think for radio, I’ll agree Terry Gross is one of the best that has ever lived. I love her so much and have so much respect for her. But for me, I still think the spectacle of Oprah, her awareness of the right moments, the right beats, the drama, makes her the best interviewer alive. I'm a media nerd and a former journalist, and I rewatch her interview with Lance Armstrong every few years because it’s just such an amazing interview. Terry Gross is amazing, and I’m not trying to take anything from her. And she’s had her dramatic moments with subjects, for sure. But Stern and Oprah have that added performer element that puts it over the top and into another level. One of the reasons I think Mike Wallace was such a good newsman and broadcaster was because of his background as an actor and game show host. He had the sensibilities for what made good television.
As for why I call Oprah a journalist and not Stern? I mean, Oprah has worked in news. She has research teams for her various shows and projects. Her talk show could definitely delve into tabloid stuff (especially in the 1980s, though she pulled back before the format became deranged in the 1990s), but like Donohue (a legit newsman), but she started working in local news when she was still in high school. She’s the definition of a broadcast journalist. For every tabloid story she’d get into (which often were often not far removed from what you’d see on Dateline or 20/20 or 60 Minutes or other newsmagazine programs), she’d also do deeper dives into reporting highlighting stuff that people in her audience didn’t know about. She'd visit places and talk to the people. And yes, she had research and fact checking teams on her show. Oprah is a journalist in my mind. She’s a populist and her audience target is different than the typical reader of FT or even the New York Times or people who regularly listen to NPR, but she’s a journalist all the same.
Stern, in comparison, is a DJ and a talk show host. He was a program director and disc jockey who then got into shock jock stuff at the height of that era and then created a genre-defining morning show. He reads headlines but he doesn’t do news. He might break news based on his questions, because he’s incredible at his job, but he’s not trying to tell a larger story or narrative. He's not going to go to a town in America that didn’t have Black people for 75 years to talk to residents and try to get to the heart of the racism. He's not going to go to Auschwitz with Elie Wiesel. What he can do is make the subjects he interviews reveal more about themselves than they planned. He can make people comfortable enough to show who they really are. And his technique is the same technique any good journalist would use, but he wouldn’t call himself a journalist and neither will I.
The line between broadcaster and broadcast journalist is thin, to be sure. And someone like Terry Gross or Charlie Rose are definitely more on the “journalism” side than Oprah usually is. But Oprah is still trying to tell broader stories. She’s still doing research. Stern is much more akin to Johnny Carson or Mike Douglas, Merv Griffin, David Letterman, etc. Oprah isn’t Diane Sawyer, but she’s closer to that direction.
Both are great and I don’t think Stern not being a journalist hurts him or his credibility or his work at all. If anything, he doesn’t have to be held to the standards of journalism or whatever. Whereas Oprah has been rightfully criticized for having people on her shows over the years spreading pseudo-science.
To put it another way, if you lie in an interview with Howard Stern and he knows you’re lying, Howard might push back on your or make fun of you a bit, but he’s going to let you go on an lie. But if you lie to Oprah, and she knows you’re lying, she'll push back. She's usually not combative, but she'll dig in more. And if she finds out you lied to her? After she defended you? She'll eviscerate you in front of a live studio audience, alongside media critics from the top newspapers in America, as part of a discussion on truth and ethics and fact checking. She'll admit her own culpability and faults, she'll take her lumps, and then she'll cut you to the core in front of God and everyone.