During the Nov. 28 episode of “The Howard Stern Show” on SiriusXM (via Mediaite), the radio host said that “Oprah’s not embarrassed by her wealth at all” and somewhat lacks self-awareness considering she frequently posts about her wealthy lifestyle despite people struggling out there in the real world.

Stern’s radio co-host Robin Quivers pushed back against Stern, claiming Oprah is merely offering a window into her life and “not showing off.”
Later in the episode, Stern was a bit more complimentary toward Oprah when discussing her annual tradition of inviting students from her South African school, The Oprah Winfrey Leadership Academy for Girls, to her home for Thankgiving.