3 Celebrities Who Took on Oprah Winfrey

As one of the most enigmatic TV personalities in the world, Oprah Winfrey is a legend on the screen. She has been a global broadcast sensation for decades and is typically seen in over 100 different nations. She is also the head of Harpo, a major production company worth tens of millions. She is, for many, a media treasure. Not everyone, though, gets on with Oprah when they meet.

Who are some of the people who decided to take her on? Who ended up on her talk show and wound her up?

Photo: @oprah/Instagram

James Frey

Frey was a guest on Oprah’s book club section, and it was a very messy experience for all involved. Frey was exposed during the book club segment for his memoirs, “A Million Little Pieces”, which Oprah ironically tore into millions of pieces.

The book was more or less a complete fabrication, and Oprah felt ashamed for endorsing the book to others. Frey was brought back so that Winfrey could tear strips off him, to the amusement of the audience.

Jonathan Franzen

Another victim of the Book Club, Franzen was someone who took exception to be selected. Sniping at the show and saying that Winfrey had a habit of choosing “one-dimensional” reading material, Oprah was quick to deselect the book and tell Franzen that he was no longer invited to the show. Naturally, Franzen took a fair bit of flak for this choice and was eventually apologetic and regretful of the decision that was made. A lesson learned, we hope.

Photo: @letterman/Instagram

David Letterman

When David Letterman spent the mid-90s trying to make a dreadful joke about Oprah Winfrey and Uma Thurman having confusing names, it went down about as well as most of his jokes. Letterman ended up in a bit of a feud with Winfrey over it, and it took until 2005 – a whole decade – for the duo to sort it out. We assume Letterman saw the error of his ways and realized that his joke wasn’t that unique, funny, or interesting – certainly not enough to have it create a years-long feud.