Post Malone's Top 20 Funniest Moments

#20: Balancing Solo Cups on His Head

While he’s great at telling a joke, some of his funnier moments come from him taking part in some random activity. He’s always out to have a good time, even if it’s something silly and inconsequential. So him publishing a video of himself balancing a comically large stack of red cups on his head was on brand in the funniest way possible. The visual alone was hysterical, but he took it to an entirely new level by adding in some dance moves from the game “Fortnite.” It proved he was still in tune to what the Internet found funny, despite his vast fame. The vibes were truly immaculate, and it ended up being the best way to advertise “Wrapped Around Your Finger.”

#19: Sharing His Dream of Meeting Ed Sheeran

One of the best parts of becoming well known has to be being acknowledged by or even befriending your own favorites. Post proved just how relatable he was by revealing his own fantasy of meeting Ed Sheeran. Rather than just say he’d like to meet him at a concert or awards show, he detailed all the different activities he’d want to do with the British singer while at “Medieval Times.” The image of them dressed up in Renaissance attire while sharing a pint of mead is priceless enough on its own, and his earnestness towards his own interests made it even better. We can only hope they’ll eventually get to spend that day together, and that it’ll be everything he hoped for and more.

#18: Posting His First Grill

Being able to laugh at yourself is such an important trait, especially if you’re going to put yourself out there to millions of people. Malone has always been aware of his own endearingly cringe moments. This was especially apparent when he posted a photo of himself as a teenager wearing a pair of sunglasses and a grill – which may or may not just be a set of braces. It was a moment of self-awareness that made him seem more human. It reminded his fans of their own blunder years and of how far Post had come since then. The fact that he felt so comfortable showing this goes to show how confident he is about his past and present self.

#17: Dancing to Shania Twain

There are some moments that make you realize how normal Post is compared to other celebrities, and this is only one of them. While at the 2019 American Music Awards, the legendary Shania Twain was performing her classic hit, “Man! I Feel Like a Woman.” While most would’ve just stood there or clapped along, he was excited to show his love for the track. He created his own choreography, and jokingly played to the camera. It immediately endeared him to viewers everywhere, making them imagine what it’d be like to party with him. It was clear he was there to have a great time, and honor an icon while doing it. His positive energy was infectious, and helped bring some life to the industry event.

#16: Taking Jimmy Fallon to Olive Garden

Jimmy Fallon got to live out the dreams of millions of people when he got an invite to dine with the artist at his favorite restaurant - Olive Garden. He had previously told the late night host about how the Italian restaurant was his favorite place to go to after every achievement — even hitting #1 on the charts. When Fallon revealed he’d never eaten there, the rapper immediately knew he had to change that. This led to a segment where the two had dinner together. It was humorous from beginning to end, whether they were sampling wine or learning Malone’s breadstick hack. The night ended with Jimmy giving him the rights to the restaurant’s old slogan, truly bringing everything full circle.

#15: Pretending to be a Dentist

A musician, a businessman, and even a dentist – is there anything he can’t do? While hanging out with his friends, he somehow managed to get his hands on some legitimate dentist equipment. The first thing he did with it? Put it on and pretended to clean his friend’s teeth. He even playfully leaned into some of the more stereotypical aspects of the profession, such as asking if he’d ever flossed. It showed how grounded the entertainer was, and how he could still relate to everyday experiences despite having been famous for so long. The fact that he still has his silly side after all these years is a testament to how normal he is under all the glitz and glamor.

#14: “Is Meatball An Fruit”

With this, he proved that he’s one of the greatest philosophers of our time. Post’s sense of humor is a product of the Internet Age, making some of his jokes stupid and comical all at once. One tweet that sums this up perfectly was when he asked if meatballs could be considered a fruit. Obviously, the answer is no — but the fact that his question seemed to be genuine made it even funnier. The incorrect grammar was the cherry on top, making it seem more like a meme from an online comedian than one of the biggest rappers in the world. What made it even funnier was his fans playing along with the joke, creating a moment that everyone in his community could enjoy.

#13: Talking About Self-Defense for Mice

There are some things people say that make you wonder what’s going on inside their head. Post in particular has wondered about things that the average person hadn’t even considered before. The best example of this comes from his appearance on “The Joe Rogan Experience.” While talking about how his cat had successfully caught and killed a mouse, the conversation soon turned into one about how felines have unfair advantages while hunting their prey. He naturally followed this up by positing the idea that if mice knew self-defense tactics, then his cat may not have won at all. Besides being hilarious to picture, it’s also a pretty solid point — and makes us wonder what other hypothetical situations he’s put this much thought into.

#12: His Jacuzzi Selfie

When it comes to subverting expectations, no one does it better than Post Malone. He can take the most luxurious experiences and still somehow make them amusing to his fanbase. Nothing sums this up better than a picture of him taken in a jacuzzi. While other celebs would’ve taken the opportunity to flex the fact they were in an elegant location, he decided to go another route. He ended up making himself the butt of the joke by having the caption reference bathroom humor instead. It perfectly summed up his own sense of humor, while also setting himself apart from his counterparts in the industry. Only he could take such a simple moment and somehow spin it into comedy gold.

#11: Turning Nursery Rhymes into Raps on “Good Mythical Morning”

While he’s made several appearances on the long running YouTube show and its spin-offs, the most memorable by far is his first collaboration with them. “Good Mythical Morning” is known for their comedic challenges and have been a staple on the platform for over a decade. A Post collaboration was unexpected but definitely welcome – especially when it was revealed they’d be turning classic nursery rhymes into hip-hop songs. He blew Rhett and Link out of the water, with his Sugarhill Gang version of “Itsy Bitsy Spider,” paying respect to their artistry and putting his own twist onto the song at the same time. His quick thinking and timing were both impeccable, proving that he could add improv to his long list of talents.

#10: Getting Called Out for Morning Beers

It’s no secret… Post Malone has a real affinity for Bud Light. He is rarely seen without one in his hand - consistently brings a few cans of the stuff to seemingly every interview he does. He also takes a “Bud Light break” at the the start of the track “Yours Truly, Austin Post” from his album “Stoney.” When sitting down with the Ebro In the Morning show at Hot 97FM, his drinking habit was called out because, as Peter Rosenberg put it: “it’s 10:09 in the morning.” Without missing a beat, Post replies “it’s Light” - as if light beers are an appropriate morning beverage. But for the record, he’s not sponsored by Bud…yet. 


#9: His First Live Stream on Twitch

Given Post Malone’s massive success, it can be easy to forget how young he is. Born in 1995, Post is a gamer, like many other young people his age. Seeing him livestream on Twitch for the first time however, was a hilarious exercise in humanizing the larger than life figure. He tries to get a feel for the service and how the chat function works, and makes little quips about his own fame and fan-appreciation over the course of the nearly 3 hour stream. But the best part is simply seeing him get into the game. He chirps, he rages, and just generally comes across as a hilarious dude to play with.

#8: Forgetting His Own Lyrics on Mass Appeal

If you’ve listened to his album, you know that Post is more than just a rapper - he mixes it up with a little dash of country, folk and rock too. So when Mass Appeal caught up with Post Malone in NYC, they thought it only natural to take the young talent to one of the most revered guitar stores in the U.S. (if not the world) - Rudy’s Music. Post is his usual charming self, regaling us with tales of his guitar playing youth. But the laugh out loud moment comes at the end of the video when Post Malone is asked to perform his acoustic jam “Feeling Whitney” and he totally forgets the lyrics to his own song!

#7: His Cringey Breakfast Club Interview

Whenever Post Malone does an interview, he leaves a lasting impression. While many celebrities try to come across a certain way, you can tell that Post just goes with the flow, being himself and saying whatever comes to mind. When he visited The Breakfast Club in 2015 however, that attitude was tested. You can tell that co-host Charlamagne Tha God has issues with the young white rapper and tries to trip him up, but Post’s self-deprecating ways and genuine approach save him.The interview feels like one big troll, and though it gets awkward at times, the results are often also quite funny - especially when Post is talking about basketball, his dad’s job, or his girlfriend.

#6: Going Undercover for GQ on “Actually Me”

GQ has a fun segment where celebrities create new accounts on social media networks and online communities like Twitter, Facebook, Quora and Reddit, and then give answers to people’s questions about them. This series usually gets good results, but there’s just something about Post Malone’s honesty that makes this episode a cut above the rest. He’s just so candid; he doesn’t give a damn about creating a mystique or aura. The answers are so innocent and hilariously honest, we can’t imagine that any of the users actually believed the real Post Malone had responded.

#5: The People vs. Post Malone

In the Noisey series “The People Vs.”, Post Malone is asked to go through the comments on his “White Iverson” video. Whether he’s getting complimented, insulted or being hit with some sort of odd combination of both, he keeps a smile plastered on his face and takes it all in stride. Again, his honesty plays a big part in making this video so funny. From his surprisingly lengthy thoughts on the character of Bolbi from Jimmy Neutron to the admission that, no, he did NOT actually sink that shot in the music video, Post Malone drops truths left right and center - all the while keeping it breezy - with the odd cussing out for good comedic effect.

#4: Having Dinner with Martha Stewart & Snoop Dogg

Martha Stewart certainly has reinvented herself, hasn’t she? Before her jail time, no one could have imagined her doing a collaboration with Snoop Dogg, or throwing such a hilarious jab at one of her dinner guests. Though this entire dinner segment is entertaining - and Post is a hoot with his many little quips and queries - Stewart steals the show when she asks what Post Malone is doing at their dinner if he only has one good song? Rather than bristle or get tripped up, Post just seems to love it. The more she rags on him, the harder he laughs. Then again, getting burned by Martha Stewart would make for a pretty novel experience. 


#3: Brian Imanuel’s Mariachi Band Surprise

Much like Post Malone, Jakarta-born Indonesian rapper/comedian Brian Imanuel, known by his stage name Rich Brian, brings his own distinct style to the rap game. In 2017, at the Rolling Loud Festival, Imanuel hired a full mariachi band to surprise the “White Iverson” rapper with a full performance of his song “Congratulations.” Suffice it to say… Post freaking loved it. The Texas rapper is all smiles as he takes in the unexpected performance, sipping on a Bud Light and dancing along to this unique rendition of his track. By the end, it’s a full blown singalong. It’s funny, but it’s also just downright heartwarming. Of course, Post soon returned the favor.

#2: “Why Don’t You Love Me?”

So… this is a whole lot of something. It seems that before Post Malone dropped “White Iverson” and caught everyone’s attention in the world of hip hop, he was doing… whatever this is. Apparently he used to go by the name of Leon DeChino and had a partner in crime by the name of Jazzy Eff. Everything about this video is absolutely ridiculous, from the production value and music to the dance moves and insane get-ups. Rap might be the industry in which Austin Richard Post found success, but given his fun-loving attitude, we can understand how he first gravitated towards comedy music. So sit back, relax, and have a good laugh courtesy of a pre-fame Post Malone.

#1: Hot Ones

If you’re ever trying to pitch someone on Post Malone as not just a musician but a personality, and only have time to show them one video… this is it. First We Feasts’ series “Hot Ones” sees celebrities answering questions while eating increasingly spicy hot wings. As you can imagine, Post Malone’s perma-chill attitude pairs hilariously with this challenge. Over the course of the 19 minute episode he gives us such classic moments as “I don’t like it” and “I think I’m gonna steal his dog.” Hearing him try to talk about his views on sauce after tackling the spiciest wing? It’s pure YouTube magic. Post Malone… thanks for the laughs!


When has Post Malone made you laugh the hardest? Let us know in the comments below.