Ellen DeGeneres is hilarious, warm, and undeniably charming on her daytime talk show, The Ellen DeGeneres Show, which has been on the air for more than 15 years. Her sweet nature puts her guests at ease, even when she asks them uncomfortable questions about their dating lives or pregnancy status.
Unfortunately, not even DeGeneres’ quick wit, humor and laid-back demeanor could salvage these awkward moments.
From a thieving audience member to a Kanye West rant to a bizarre misunderstanding with Ryan Seacrest, some of these segments are more cringe-worthy than comical.
In May 2016, Kanye West literally left DeGeneres speechless. She asked him if he has regretted anything he’s tweeted, and the rapper launched into a rant lasting more than six straight minutes. His tangents included everything from his artistry to fashion design to bullying to race to Facebook.
It was clear that at a certain point, DeGeneres decided to just sit back without interjecting and let him get everything off his chest.
In light of the psychotic breakdown the rapper suffered six months later, his rant on Ellen has morphed from something originally interpreted as silly to somewhat dark and sad.
In May 2017, singer Jessica Simpson gave an interview with DeGeneres that was such a trainwreck, the hostess couldn’t keep a straight face.
Simpson started off the interview slurring and sounding slightly out of breath, insisting to DeGeneres that she wasn’t pregnant. It got worse from there.
She discussed mermaids not being allowed to pee on her children, the definition of “manhandling,” and the duration of her relationship with her husband –which was a bit unclear. She mentioned that her husband may or may not give her massages while he’s sleeping, and then discussed her billion dollar fashion empire.
DeGeneres broke the fourth wall several times to give a look to the viewers at home, but she eventually cut to a commercial to put Simpson and the audience out of their respective miseries.
DeGeneres confronted Caitlyn Jenner about her conservative views on marriage equality in a September 2015 sit-down that forced the transgender activist to later clarify her opinions.
She went on to say that over time, she doesn’t want to , quote, “stand in front of anybody’s happiness.”
DeGeneres, who’s married to Portia De Rossi, gently pointed out that the word “marriage” is in fact important because she wants the same word that everyone else has.
After the episode aired, Jenner wrote on her website, “Like many people, there was a time when I didn’t realize how important it is for gay couples to have the right to get married. After hearing from my gay friends and learning more about the hardships they faced because of discrimination, it became clear to me that everyone should be able to marry the person they love.”
In 2017, pop superstar Katy Perry appeared on Ellen to play “Will You Perry Me,” a version of “Who Would You Rather.”
Before the game began, the singer whined….
Apparently, DeGeneres forgot Perry ever had a husband. Visibly wanting to change the subject, Perry motions to the producers behind the scenes in an effort to cut the segment –but to no avail.
In this 2017 episode, actress Nicole Kidman perfectly shades fellow guest and Food Network star Giada De Laurentiis.
The ladies begin by making artichoke arancini, which they roll into balls. DeLaurentiis asks DeGeneres if she’s ever, quote,”made any kind of balls,” and DeGeneres breaks the fourth wall, turning to the crowd for laughs.
deLaurentiis then asks Kidman if she’s ever made any balls…
Moments later, DeLaurentiis appears to be impressed with Kidman’s arancini ball rolling..
When it’s time to actually cook the balls, Kidman asks DeLaurentiis where the timer is and rolls her eyes when DeLaurentiis informs her there is no timer.
Once DeGeneres and Kidman sample DeLaurentiis’ finished plate, they are not impressed, to say the least. DeGeneres chews for a while, and Kidman gives a visibly flustered DeLaurentiis her review…
In a June 2017 segment designed to see just how honest her studio audience is , DeGeneres caught several would-be thieves.
She set up a table with free swag and a sign that instructed audience members to only take one item. Most audience members were honest and didn’ take more than one item…but then there was Nancy. Nancy takes a cup, a keychain, a shirt, and a shot glass, and then when her friend asks her if she’s taking extra swag , Nancy tells her to “shut up.”
A bit later, Nancy returns one of her stolen items and swaps it out for a hat. Unfortunately for Nancy, DeGeneres calls her out in front of everyone.
DeGeneres then makes Nancy sit in “Ellen Jail” on the stage.
In January 2008, Ryan Seacrest appeared on The Ellen DeGeneres Show on her birthday and gave her a Bingo game for them to play at her regular game nights.
Toward the end of the segment, Seacrest finds a small gift bag near his seat. A horrified Seacrest clearly thinks the blue metallic bingo marker is, well, something much more inappropriate for daytime TV.
In his best attempt to change the subject, Seacrest tries to play some bingo.