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Top 10 Most Hilarious Keeping Up with the Kardashians Moments

VO: Lisa Yang WRITTEN BY: Mark Sammut
Whether reality or fiction, funny is funny! For this list, we’re looking at those moments when the Kardashians – intentionally or accidentally – produced comedy gold. Join MsMojo as we count down our picks for the Top 10 Most Hilarious Keeping Up with the Kardashians Moments.

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Top 10 Most Hilarious Keeping Up with the Kardashians Moments

Whether reality or fiction, funny is funny! Welcome to MsMojo, and today we’ll be counting down our picks for the Top 10 Most Hilarious Keeping Up with the Kardashians Moments.

For this list, we’re looking at those moments when the Kardashians – intentionally or accidentally – produced comedy gold.

#10: Scott Prank Calls Kris as Todd Kraines

Like any reality show about the rich and famous, "Keeping up with the Kardashians" has a couple of running gags, including one involving a family friend, a hilariously bad impersonation, and an oblivious Kris Jenner. Fed lines by Kourtney, Scott Disick prank called the famous momager pretending to be Todd Kraines, a real life luxury lifestyle agent who had no idea what was going on . . . and the rest is history! At the time, Scott had no idea who Todd was, a fact that only made the whole thing all that funnier.

#9: A Drunk Kris Falls into the Pool

Whenever the wine starts to flow, magic tends to happen! Whether delivering or on the receiving end of a punchline, Kris Jenner is a constant source of comedy! Ever since the mum drunkenly elected to get a tattoo, Kris has repeatedly stolen the show by simply letting the alcohol do the talking. The family's wine tasting trip to Napa ranks among the series' more memorable moments; however, nothing beats a tipsy Kris jumping into a pool while straddling a penguin float. Kourtney's reaction speaks volumes.

#8: Kris’s Allergic Reaction

Before everyone grew obsessed with Kylie Jenner's fuller lips, another Kardashian's mouth ended up seizing the headlines. Unfortunately, Kris' swollen appearance was not pre-planned. During a family trip to the Dominican Republic, the momager was bitten by an insect, causing the reality star's upper lip to swell to the size of a sausage. Kris was understandably upset by the surprising turn of events, but the same could not be said for the rest of the family. Now, in all fairness, people pay good money for this type of look.

#7: Kris & Khloé TP Kim’s Place

Nobody likes feeling ignored. Coincidentally, nobody appreciates coming home to a house covered in toilet paper either. Unable to join-in on Kim and Kourtney's bonding session over babies, Khloé vented to Kris over a couple of drinks. Before anyone could say tequila, one thing led to another and Kim's house was TPed. The vandals would have gotten away with it too, if it weren't for those meddling security cameras . . . oh and Khloé spraying Kris' name on a wall. If a prank is good enough for a frat house, it is good enough for "Keeping Up with the Kardashians."

#6: Kim's Cry Face

This may sound kind of mean, but Kim's cry face is hilarious! After all these years and countless iterations, the Kardashian sibling's expression while sobbing has become something of a meme, and Kourtney was among the first to point out her sister's unfortunate cry face. Regardless of the situation's sincerity or whether the waterworks seem warranted or not, Kim's cry face guarantees that no scene ever gets too serious or heartbreaking. For better or worse, "Keeping Up with the Kardashian" taught viewers the importance of finding humor in tragedy.

#5: Kourtney’s Mouth Is Frozen after a Visit to the Dentist

This moment is documented proof of why everyone hates going to the dentist. After having some work done on a molar, Kourtney met Khloé for a nice relaxing lunch. Or, that would have been the case if the oldest Kardashian sister could talk or smile. With the right side of Kourtney's face completely numb after an earlier dentist appointment, the stylish celebrity presented an easy target for some classic sibling mockery. Apparently, not even temporary paralysis is enough to discourage a Kardashian from appearing in front of cameras. After all, the show must go on.

#4: Welcome to the Hood

When it comes to reality shows, one has to expect a certain amount of cringe humor. However, nobody was prepared for this! Earnestly playing the part of the friendly neighbor, a role Kris typically knocks out of the park, the celebrity tried and failed to prove that she was one of the cool moms. Just in case the "Welcome to the hood" part was not cringy enough, and it most certainly was, Kris opted to spit some bars for good measure. Please, someone, drop the mic!

#3: Kim Takes a Selfie as Khloé Heads to Jail

One of the more controversial early "Keeping Up with the Kardashians" incidents saw Khloé violating probation and, sequentially, heading to jail. Due to overcrowding, the youngest Kardashian spent less than one day behind bars, but the family was understandably worried as they accompanied Khloé to jail. Well, everyone except Kim, who dedicated the entire drive to taking selfies and ignoring the soon-to-be prisoner. Finally, Kris had enough of the celebrity's behavior and scolded Kim for being so self-absorbed. To be fair, everyone grieves in their own way.

#2: Kim Loses an Earring

During a trip to Bora Bora, Kim was playfully thrown into the ocean by future ex-husband, Kris Humphries. What happened next belongs in reality TV hall of fame! Following a brief period of jubilation, Kim suddenly realized that she was one earring down and started to panic. Assuming the $75,000 piece of jewelry had sunk to the bottom of the ocean, Kim responded by unleashing the waterworks, which – as everyone knows – is almost always hilarious. In due time, the earring turned up safe and sound, but Kim's reaction will be remembered forever.

Before we unveil our top pick, here are a few honorable mentions.

Kylie and Kendall Impersonate Kim

Kris Walks in on a Naked Scott

Kris Prank Calls Random People

#1: Sisters Fight after Kim Buys a Bentley

Sibling squabbles are common in most families, and the Kardashians are no exception. Early on in the show's run, Kim's fame overshadowed the rest of the cast, a fact that caused a bit of tension between the sisters. Annoyed by Khloé and Kourtney's behavior at a car dealership, Kim armed herself with a purse and launched a counter-attack. Swinging wildly in Khloé's general direction while spouting insults and iconic one-liners, Kim's outburst suggests someone should think twice before annoying the celebrity. Hell hath no fury like a Kardashian scorned.


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