6 most awkward moments on The Ellen DeGeneres Show: cringeworthy interviews with Taylor Swift, Justin Bieber, Caitlyn Jenner and more

- The just-cancelled hit talk show had its misses too, like that game based on Grammy award-winning Taylor Swift’s dating life that the singer begged to stop
- DeGeneres also displayed a censored nude of Justin Bieber, challenged Caitlyn Jenner about her LGBT views and had a spat with Dakota Johnson
Ellen DeGeneres announced the end of her daytime talk show on Wednesday (May 12). While the show will be remembered for its funny bits, charitable moments of giving and plenty more, its 19-year run definitely had its awkward moments too.
Here’s a list of some of the most cringeworthy interviews:
Justin Bieber

DeGeneres had Justin Bieber on her show in November 2015. On television, the two are typically seen as close friends, but on this episode, their conversation was more uncomfortable than friendly. Before Bieber’s appearance, a new paparazzi photo of him was released, showing the then 21-year-old nude while on holiday. DeGeneres displayed the censored version of the photo on the giant screen behind her, asking Bieber to explain what happened.
Wendy Williams

Less than a year later, DeGeneres brought on daytime talk show host Wendy Williams. The negative energy between these two was clear. While speaking with Williams, DeGeneres wasn’t her usual quirky and extroverted self, and let Williams take most of the time of their interview.
The interview quickly shifted toward the two playing DeGeneres’ popular game Head’s Up in which Williams was tasked with acting out a celebrity that DeGeneres would guess. Bieber came up again and Williams delivered a cringeworthy remark mid-game.