When Kourtney Kardashian Laughed at Her 'Sobbing' Sister Kim: "You Have An Ugly Crying Face"

Kim Kardashian's (in)famous "ugly crying face" is no secret now. However, the inception of it was back from a segment from their reality TV drama Keeping Up with the Kardashians. The queen of wits, Kourtney Kardashian, laughed mercilessly at the SKIMS founder for crying and even passed some hurtful remarks.

The Kardashian sibling, Khloe, took to Instagram to post a throwback video of the eldest, Kourtney, making fun of "sobbing" Kim. The video clip was part of the half-hour Keeping Up: Kardashians On Vacation special that aired on E! in May 2008. The drama unfolded when the 42-year-old was caught on camera, dejected and inconsolable. 

The camera focused on Kim, who yelled at the POOSH founder, "It's not funny; get out of here if you're going to continue to laugh at me. I'm tired of it." The lens shifted and panned to the eldest Kourtney at the other corner of the room, heartlessly laughing and denying, "I am not," with a big smile on her face. 

The scene had the other two siblings- Khloe and brother Robert, looking confused and solemn. The scene then cuts to the Lemme founder, who was heard saying in a confessional, "I start laughing at Kim when she's crying because I just can't help it; she has this ugly crying face that she makes." 

The clip continued to show the mother-of-four crying harder than before as she vented, "You're sitting there laughing. It's not funny." However, Kourtney kept denying that she didn't find it funny, but her face contradicted her claims. The clip was part of the Kardashian's ski trip in Colorado.

The vacation was arranged by their stepfather, Caitlyn (formerly Bruce) Jenner, in an attempt to ease the family tension. But all in vain, as the others seemed to have ganged up against Kim. Fortunately, the brawl was a thing of the past, and the sisters grew up from that episode and moved on with their lives. 

However, the fashion mogul's "ugly crying face" metamorphosed into an iconic meme, to the extent that on Tenor, there are GIFs in the name of 'Kim's ugly crying face.' In one of her encounters with pop sensation Katy Perry, the Hulu star bonded with the Fireworks singer over their expressions while crying. 

The Roar singer was brought to tears by an American Idol contestant, Fire's last-minute duet with Jayna Elise, and she posted the video on her Instagram account alongside the caption, "Hi, this is my ugly cry face. Watch #idol now to get us," as reported by E! News. Kim, who already mastered the "ugly crying face," found the singer's post relatable. 

She commented on the 38-year-old American musician's post, "We all have one." Later, in 2012, Kim addressed her iconic crying face during the filming of KUWTK over her then-marriage to Kris Humphries. "Ok, I have to admit I do not look cute crying. LOL! And I do cry a lot," she wrote on her blog. 

Editor's note: This article was originally published on September 21, 2023. It has since been updated.