The Oprah Winfrey Show aired for an astonishing 25 seasons and accumulated an equally incredible 4,561 shows or episodes. Now that sure is a lot of guests.
In her tenure as leading television host, Oprah had many guests on the show, ranging from medical professionals to normal, everyday people and, of course, celebrities. Now the last category was sure to get a lot of ratings and over the years, with many episodes dedicated to stars making the most headlines.
But not all of these interviews went off as planned. Sometimes, the stories at hand were a tad too controversial, or even the interviews themselves kind of took some interesting directions, so to speak.
Regardless what the reasons, here are some pretty interesting moments from the show, and as always, we’ll take the bad with the good.
15 Regretted Being On Oprah: Lance Armstrong - She Was A Tad Too Hard On This Legendary Cyclist
It was big news when Lance Armstrong admitted to ‘having a little help’ at winning all of those bicycle races over the years.
But when he went on Oprah to talk about his side of things, many believed that it was she that was a tad too on the offensive, doling out hard-hitting questions with quite a bit of an edge to her tone.
14 Would Return In A Heartbeat: John Travolta - BFFs Until The End
Now this megastar has had his epic moments on the old Oprah Winfrey Couch. He and she are great friends, and if he isn't talking about his latest film project, they always find things to talk about… from food to dancing, exercise, flying, well, we're sure you get the picture.
John would visit with Oprah no matter the occasion, we're sure.
13 Regretted Being On Oprah: Tom Cruise - He Was Coerced Into Displaying His Feelings
Journalists are trained to gain a subject’s trust, and then betray it to gain info—a school of thought she has shown often in her interviews. This was quite obvious in Oprah's infamous interview with Tom Cruise.
Well, Oprah got him to open up about his then relationship with Katie Holmes, and well, the rest is history. He’ll never live that couch hopping down, poor dude.
12 Would Return In A Heartbeat: Mitch Albom - Always An Oprah's Book Club Selection
Over the years, Oprah has had a lot of authors on her show. Oprah’s Book Club is pretty renowned, and if you make her list, rest assured you’re in for some pretty decent sales.
Mitch Albom was definitely given the honor, and not only that, but she financed the made-for-TV film based on his first novel, Tuesdays With Morrie.
11 Would Return In A Heartbeat: Madonna - The Queen Of Pop
Before there was Lady Gaga, there was Madonna, an icon of multiple ages. But maybe we’re biased, as she definitely was popular in the eighties, nineties and new millennium.
But bias aside, she is untouchable and will rein for many years to come. Her performance on the Oprah Winfrey Show was epic and she’d return to chat with Oprah any day of the week.
10 Regretted Being On Oprah: James Frey - A Big 'No-No' In Oprah's Book
James Frey is the author of three best-selling books. But it was his first book, A Million Little Pieces, that garnered him the most attention. In Oprah’s aforementioned Book Club, she prefers to feature real stories based on real events.
Well, when it came out that Frey's novel was a bit more fiction than fact, Oprah publicly admonished the author.
9 Would Return In A Heartbeat: J.K. Rowling - From One Queen To Another
There probably isn’t a more successful writer in the business today, and it’s all because of her characters in the Harry Potter series of books that did it.
But this woman knocked past mega-hit authors out of their positions (with a little help from Harry). Her appearance on Oprah was a great way to get to know her story.
8 Would Return In A Heartbeat: The Cast Of Friends - The Appearance Served As A Promo
The television sitcom Friends was a global phenomenon, and it basically launched these charismatic six actors. For the duration of ten years, the show was indeed ‘must-see TV,’ as the network, NBC was fond of saying.
It was during the beginnings of the show’s influence that the entire cast was on Oprah and it definitely helped launch them to prominence.
7 Regretted Being On Oprah: Hugh Jackman - A Good But Traumatizing Experience
Hugh Jackman, aka, Wolverine, is known for doing a few of his own stunts. In great shape, the man is definitely comfortable getting physical during his film shoots, so when the opportunity came to perform this zip line stunt on Oprah, he jumped at the chance—literally!
It almost went very sour and very quickly at that. He sustained injuries, but at least the interview itself wasn’t as tough.
6 Regretted Being On Oprah: Elizabeth Taylor - Refusal To Answer Questions
Elizabeth Taylor was the queen of cinema during the mid to late 20th century. But being used to the public eye for so many years didn’t mean she liked being asked about her personal life.
On her appearance on the show, Elizabeth refused to answer any questions regarding her very personal life, which made for some awkward moments.
5 Would Return In A Heartbeat: Sylvester Stallone - Dodging A Few Tough Questions
Sylvester Stallone is definitely an icon, and soon, he’ll be celebrating 50 years in the business known as ‘Show Business.’
But it was in 1988 that he was going through a pretty tough divorce, and with the launch of the third installment in the Rambo series of films, he allowed Oprah into a home he was renting at the time and answered a barrage of tough questions.
4 Regretted Being On The Show: Barbara Streisand - A Painted Mic!?
Now we must admit, she definitely made a few appearances, but there was in fact one that Barbara Streisand will never be able to live down.
On one of her appearances, she actually requested that the microphone she used be spray painted white to match the set, the couch, her clothes, and yes her little dog. Um, what?
3 Would Return In A Heartbeat: Dr. Oz - Always 'The Authority' On Your Health
Dr. Oz is the type of guy you could listen to for hours, and at the same time, he can also scare the living life out of you if you take everything he says word for word.
He knows what’ll hurt you, and it was these qualities that Oprah saw in him when she had him on the show early on and helped launch his fame.
2 Would Return In A Heartbeat: Dr. Phil - She Launched His TV Run
Oprah did the same thing for Dr. Phil, who has enjoyed a very long tenure on TV as well. He’s helped many get over a plethora of issues, including psychological problems, and of course, relationship woes.
Oprah and he remain friends to this day and he sure is grateful for the help she gave him at the start of his TV fame.
1 Regretted Being On The Show: Jay Leno - Grilled Him A Tad Too Hard
Before Jimmy Fallon, Jay Leno was the man to see, and after he retired the first time, his spot was given to Conan O’Brien. However, quickly thereafter, the show was given back to Jay.
The moment in TV history was caught up in a lot of controversy. And at the height of all that controversy, Oprah was right there, ready to ask the tough questions.
Sources: Wikipedia, Oprah