Keep your friends close and your enemies closer – or, if you are Howard Stern, never let them know which category they fall into.

Stern opened up about his rumored decades-long feud with media mogul Oprah Winfreyboth 71, during a recent episode of Andy Cohen’s SiriusXM show Andy Cohen Live.

During the interview, Cohen57, asked Stern about his ‘enemies,’ and who the controversial shock jock has repaired his relationships with over the years.

‘I think about who are Howard Stern’s enemies at this point or punching bags,’ Cohen mused during the episode.

‘And I get the sense that you’ve either publicly or privately kind of mended fences with them. But it seems like Oprah might be the only Howard Stern foe or enemy that you still have?’ he asked the radio host.

However, Stern insisted that’s not the case.

‘No, I love Oprah,’ Stern replied, with a surprised Cohen replying: ‘You do?’

‘I follow Oprah. I enjoy watching Oprah,’ Stern said, admitting he’s never actually spoken to Winfrey.

‘I think she’s afraid,’ he continued. ‘I know (Winfrey’s best friend) Gayle King very well. And I think at one point she suggested, “Oh, we should get together with Oprah.” I said, “You better check with Oprah. You better. Don’t surprise her with me.”‘

He later admitted he’s ‘fascinated by Oprah.’

‘I like sometimes how Oprah is so unaware,’ he explained during the show. ‘Maybe she is aware, but I suspect – I’m an Oprah follower – sometimes she’s unaware of the way she shows her wealth.’

He declared he ‘couldn’t do that,’ and clarified he doesn’t think she’s wrong, but has some issues with her opulence in the current climate.

‘We all know she’s wealthy,’ he pointed out. ‘But I think in the world right now, there is such a disparity between those who have and those who have not. And it’s only getting worse… so I find it funny.’

‘And I’m not gonna sit there and tell you I don’t think it’s funny. I go, “Wow, Oprah is unapologetically wealthy,” and good for her. But I don’t hate Oprah at all. I think she’s brilliant.’

Stern and Winfrey’s apparent feud goes back to 2004, after he called on the Federal Communications Commission to investigate The Oprah Winfrey Show over potentially indecent content on the program, following the agency’s crackdown on his show.

In 2022, Stern called out the media mogul for showing off her lavish lifestyle on social media.

The controversial radio host spoke about how Winfrey ‘loves showing off’ her wealth and is ‘not embarrassed by’ it during an episode of The Howard Stern Show.

‘It’s f***ing mind-blowing when you follow her on Instagram,’ he told his co-host Robin Quivers, before adding, ‘You gotta be a little self-aware and know that there are people struggling out there.’

‘Oprah’s not embarrassed by her wealth at all,’ he said. Stern also stated that when you follow the famed talk show host on Instagram you ‘see her estates, her gardens, the people who service her.’

Stern continued his critique, adding that Oprah ‘knows’ how to be rich and ‘likes’ to show it off.

‘Which is something I’m not comfortable with,’ he added. ‘I don’t think that people should show off their wealth.’

Quivers responded by insisting: ‘Oprah’s just showing you her life. She’s not showing off.’

However, Stern said he didn’t see it that way and her posts lacked self-awareness.

‘You gotta be a little self-aware and know that there are people struggling out there, Robin. You got to. You gotta kind of think about people who don’t have — to eat. You know what I’m saying? I mean, come on. You gotta be a little bit aware of this.’