Top 10 Most Awkward Ellen Moments



Top 10 Most Awkward Ellen Moments

VOICE OVER: Rebecca Brayton WRITTEN BY: Tal Fox
The most awkward Ellen moments are impossible to look away from, no matter how hard you try. For this list, we'll only be considering uncomfortable moments with Ellen's celebrity guests, as there's only so much awkwardness we can handle in one list.
You know when you don’t want to watch but you just can’t look away? Welcome to MsMojo and today we’re counting our picks for the Top 10 Most Awkward Ellen Moments.

For this list, we’ll only be considering uncomfortable moments with Ellen’s celebrity guests, as there’s only so much awkwardness we can handle in one list.

#10: When Wendy Williams Told Ellen She Looks Like Justin Bieber

The animosity between these talk show hosts didn’t go unnoticed by the viewers. And if things weren't already uncomfortable enough, a game of “Heads Up!” sent our cringe scale through the roof. Ellen would quickly regret joking about Wendy’s unapologetic honesty after she found herself the subject of it, when Williams claimed that she looks like Justin Bieber. We can see that our host was clearly thrown by the comparison but, while the rest of us were left squirming in our seats, she just laughed it off like a pro.

#9: When Celine Dion Clapped Back Over Her Son’s Hair

The Canadian singer is normally easygoing and funny when she makes the talk-show rounds. However, when Ellen took a jab at her son’s hair, this mamma bear was not impressed and instantly went on the defense. After asking Ellen if she has a problem with her son’s appearance, she proceeded to lay down the law about critiquing her child. And as the atmosphere in the studio turned frosty, it’s very obvious that Ellen has hit a nerve. Despite the host’s best attempts to move the conversation along, the awkwardness continued to linger.

#8: When Ellen Grilled Taylor Swift About Her Love Life

Taylor Swift’s love life is a pretty well-covered topic thanks to her music but that doesn’t mean she can’t set some boundaries. This wasn’t the only time Ellen grilled the singer about her dating history, but it is the most uncomfortable to watch. Ellen was relentless in quizzing Swift about who she’s dated, even turning it into a game until Taylor finally cracked and demanded she stop. We can feel the awkwardness radiate through the TV, but somehow Ellen missed all the signals, and trust us, they’re not all that subtle.

#7: When Ryan Seacrest Gave Ellen a Birthday Present

Everyone loves receiving presents, but when Ryan Seacrest gifted Ellen a bingo set for her 50th birthday, as a humorous jab at her age, little did he know it would become the gift that kept on giving. Now, any bingo aficionado would know what an ink dauber is, but Seacrest was visibly startled by the object and it doesn’t take long before everyone realized what he was thinking. This moment was definitely more embarrassing for him than anyone else but, come on, man, it’s a family show, what were you thinking?

#6: The Whole Jessica Simpson Interview

This interview made us cringe so hard at the time, but has turned out to be so sad. When Jessica Simpson popped by to talk about her music and fashion line, things pretty much went off the rails from the moment she sat down. Whether she was talking about relationships and pregnancies or mermaid parties, like Ellen, we were at a total loss for words at how quickly things took a turn for the bizarre. But Simpson acknowledged in 2020 that she was actually drunk at the time, as she wrestled with addiction. That put the cringe in a whole new tragic light.

#5: When Ellen Forgot Katy Perry Had Been Married

Remember when Katy Perry married Russell Brand? Ellen didn’t. In fact, when she announced a game called, “Will You Perry Me” the singer joked about not wanting to get married again but she’s just met with a blank stare from the host. Perry awkwardly reminded her of her short-lived marriage to the British comedian and even brought up the fact that she gave her wedding presents on the show. Even audiences at home could feel the painfulness of this exchange and fingers everywhere etched for the remote just to escape the awkwardness.

#4: When Ellen Cooked with Giada De Laurentiis

If Nicole Kidman thought reliving her bizarre Oscars clap would be the most uncomfortable moment in this episode, Giada De Laurentiis soon made us all forget about that with a rather bewildering cooking segment. Viewers were left unimpressed by her condescending and rude manner, and Kidman’s side glances and eye rolls are about as subtle as the chef’s tactlessness throughout the segment. Clearly Nicole had enough, as she threw back some shade of her own. You know what they say, if you can’t stand the heat, get out of the kitchen.

#3: When Ellen & Caitlyn Jenner Discussed Same-Sex Marriage

Caitlyn Jenner is a vocal advocate for LGBTQ+ rights . . . that is, until the subject of same-sex marriage. So you can imagine things got tense when the host broached the subject that is so obviously close to her heart. Jenner momentarily got defensive when Ellen pointed out that she’s a Republican, but despite claiming that her views have now changed, Ellen doesn’t seem to be convinced at all of that. As Ellen continued to challenge her guest, both sides managed to stay cool and composed. Nevertheless, you could have cut the tension in the studio with a knife.

#2: Kanye’s Rant

This hip hop legend is notorious for his unpredictable behavior, and this is hardly the only time he has left his hosts at a loss for words. During this interview, Kanye went on what can only be described as a monologue, that lasted for around six minutes. His erratic train-of-thought was met by silence in the studio, and even Ellen knew that there was nothing she could do to get this interview back on track. He concluded by apologizing for getting real on daytime television and, miraculously, Ellen actually managed to get in the final word.

#1: When Dakota Johnson Called Ellen Out for Missing Her 30th Birthday Party

As we’ve seen already, Ellen’s memory can get her into a lot of trouble. When Ellen called out Dakota for not inviting her to her 30th birthday party, the actress doesn’t miss a beat in shutting this false accusation down. Not only, it turned out, was Ellen invited, but she didn’t even give a reason for not attending. Dakota then told Ellen how her favorite comedian, Tig Notaro, performed at her party and Ellen’s face dropped instantly. Johnson then swooped in mercifully — or was it sharply — with an “ . . . other than you”. Get ready to squirm in your seat!