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

May 19 , 2021

Not all of Ellen DeGeneres’ interviews were hits; her chats with Caitlyn Jenner, Dakota Johnson and Taylor Swift bombed particularly hard. Photos: Handouts, YouTube

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:

How does Ellen DeGeneres spend her US$370 million net worth?

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.

Court victories for Michael Jackson

Taylor Swift

Despite the fact that Taylor Swift must have a lot to talk about, especially considering her musical talent and her Grammys to go with it, over the course of her career, many have been razor-focused on her love life instead. Swift has had a long dating history, and DeGeneres thought it would be comical to bring that up on her show in the form of a game involving a cowbell. As the list grew longer, Swift became more uncomfortable and begged for the game to end. This segment was particularly hard to watch.

Caitlyn Jenner

Before Caitlyn Jenner announced her surprise run for California governor, DeGeneres had her on the show to discuss a variety of topics – including same-sex marriage, obviously an important subject for DeGeneres, as she herself is lesbian and is married to Portia de Rossi. But Jenner is openly conservative and during their conversation, DeGeneres pointed this out in a blunt way. Before coming out as transgender and changing her views, Jenner was against same-sex marriage. DeGeneres decided to challenge Jenner to see if her views really did change, and the tension was palpable.

Who’s the richest Shark Tank cast member?

Dakota Johnson

Dakota Johnson was featured as a guest in 2019, following her 30th birthday. The interview opened with DeGeneres asking about her birthday party and remarking that she wasn’t invited. Johnson immediately clapped back, saying that DeGeneres was invited to the party but just failed to show up. She also mentioned how in previous appearances, DeGeneres had given her “s***” about not being invited to previous parties she held. DeGeneres was visibly stunned by the whole situation, and audiences in the studio and at home must have felt similarly.

Sofia Vergara

Sofia Vergara and DeGeneres are typically regarded as close friends based on interactions they have shared over the years. However, in one appearance, DeGeneres and Vergara played a game that seemingly targeted Vergara’s accent. The interaction was humiliating to say the least.

Want more stories like this? Sign up here. Follow STYLE on Facebook, Instagram, YouTube and Twitter.

Fame and celebrity

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