From a few accidentally-on-purpose innuendos to slips of the tongue and sticking it to difficult guests, Oprah Winfrey knew how to make good TV during her 25-year run hosting The Oprah Winfrey Show, which left the air in 2011.
However, on Monday's episode of Harry, the roles were reversed when host Harry Connick Jr. had Miss Winfrey in the hot seat to promote her latest book, The Wisdom of Sundays: Life-Changing Insights from Super Soul Conversations.
When the crooner-turned-talk-show host asked the media mogul who her "worst" guest ever was, the billionaire producer revealed that a lawyer who couldn't stop name dropping his book topped her naughty list.
That got us thinking about her many jaw-dropping moments over the years, which there were plenty of, as well as her plethora of awkward encounters with guests.
Check out the top five most awkward interviews over the years...