Top 10 Cringiest Pete Davidson Moments

Nobody likes seeing someone chew with their mouth open. Unfortunately, millions of viewers were witnesses to this bad habit thanks to Pete Davidson. During the 2018 Video Music Awards, his then-fiancée, Ariana Grande, received the award for best pop music video. As she walked onstage, a camera caught Davidson chewing gum with wild abandon. A later shot revealed that he was still going at it while Grande gave her speech. You’d think someone who is on live TV weekly would be more careful about being caught with his mouth open. Then again, it’s completely possible that Davidson didn’t care who saw his tonsils.

Four years after Ariana Grande’s grandfather passed away, she posted an endearing old picture of them together on Instagram. Later that day, Davidson commented “omg what a cutie” on the photo. An impassioned section of Grande’s followers called him out for trying to compliment his fiancée during a somber occasion. Davidson replied that his remark was aimed at her grandfather and criticized people for trying to start drama. Although his cutie comment is open to misinterpretation, zealous commentators might be more to blame than anyone here for this awkward exchange.

Justin Bieber's dad Jeremy isn’t considered to be the most upstanding individual. He’s gotten in trouble with the law and even walked out on his popstar son for a while. This gave Davidson enough reason to make a blistering joke at the Justin Bieber roast. The comedian began by noting that he regrets losing his father in the 9/11 attacks. However, meeting Jeremy Bieber was so apparently so terrible, it made Davidson happy he grew up without a father. The punchline drew both laughs and gasps from the crowd - one of those moments when you’re not sure whether to laugh, cringe, or maybe a mixture of both.

Davidson and Grande weren't exactly been shy about their relationship. The engagement ring, their declarations of love, the constant talk of their bedroom habits... Needless to say, the public didn’t need to see more of their PDA in this awkward Instagram video. In the post, Davidson goes in to kiss Grande tongue-first. Instead of moving away, she turns, enabling his tongue to go on top of hers. Thankfully, the video ends before we see more of their unorthodox kissing style. It’s a short post, but the image of their tongues crossing was forever burned on the back of some people’s eyeballs.

What’s the best way to show your support for a politician? If you’re Pete Davidson, the answer is new ink. In 2017, he showed off his new leg tattoo of Hillary Clinton on Instagram while calling her a hero in his captions. The tattoo itself isn’t atrocious, exactly, but it’s not easy to tell who it is at first glance. While a few of his followers roasted the political ink, Hillary herself responded with her seal of approval. No matter what people think of the unconventional tattoo choice, Davidson will always be able to take comfort that his hero was a fan.

During Aretha Franklin’s funeral, Ariana Grande was subjected to a couple of questionable encounters. After Bill Clinton appeared to check her out, Bishop Charles H. Ellis III made a cheap joke about Grande’s name before placing his hand on the side of her . . . chest? When Davidson was asked how he felt about both incidents on Howard Stern’s radio show, he joked about how proud he was seeing Clinton’s eyes glued to Grande, and opined that the bishop’s hand placement was probably unintentional. This enraged some Ariana fans, who felt he was objectifying his then-fiancée.

Davidson’s reaction to the Aretha Franklin funeral affair wasn’t the only controversial part of his Howard Stern interview. In 2018, the comedian spent time in Syracuse, New York working on the movie “Big Time Adolescence,” but he didn’t seem to like the city much. Davidson called Syracuse “trash” and claimed it was “worse” than his hometown, Staten Island. Locals were not happy to have their city insulted by an outsider. Their backlash was severe enough to make Davidson’s friends cancel a planned Syracuse comedy show. While the incident was unfortunate for everyone, we hope it doesn’t discourage him from his characteristically blunt style of humour.

It seems like Davidson can’t go a week without controversy cropping up around his relationship. On the 44th season premiere of “Saturday Night Live”, he spoke about his engagement on the Weekend Update. But when he joked about swapping Grande’s birth control with mints in order to baby trap her, and ensure the continuation of his now lavish lifestyle, he struck a nerve with some viewers, and the joke quickly turned sour. Tirades on twitter attacked him for making light of abusive behaviour, condemning the comedian as creepy and inappropriate.

Never one to let the dust settle before mining recent events for humour, Davidson was roundly criticized when he settled on an essay written by basketball player Kevin Love, detailing how a panic attack caused him to seek out counseling. To Davidson’s credit, he began by expressing support for Love’s decision to share. However, he then joked that his own mental issues were worse, and so the athlete really should’ve “stayed in his lane”. Some viewers felt the comedian used SNL to trivialize Love’s panic attack, and that his approach distracted from the message that it’s alright to talk about mental health issues.

An Ariana Grande concert in Manchester was marred by tragedy in 2017 when a suicide bomber killed twenty-two people. That same year, Davidson used the horrific event to make a joke during a stand-up set. According to audience members, the comedian implied Ariana Grande reached new heights as a celebrity because a terrorist never attacked a Britney Spears concert. The joke drew massive criticism online and from the victims’ loved ones. When Grande addressed the controversy, she supported Davidson’s right to create edgy humor but still called the Manchester joke unfunny. Although Davidson has used comedy to talk about terrorism before, this joke came out way too soon.