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VOICE OVER: Phoebe de Jeu WRITTEN BY: Nathan Sharp
It happens to the best of us, but these are nonetheless the most awkward handshakes of all time. For this list, we'll be looking at the most hilariously bizarre and awkward handshakes of all time. Our countdown includes Conan O'Brien & PewDiePie, Joseph Gordon-Levitt & Stephen Merchant, Donald Trump & Shinzo Abe, and more!
Script Written by Nathan Sharp It happens to the best of us. Welcome to WatchMojo, and today we’ll be counting down our picks for the Top 10 most awkward handshakes of all time. For this list, we’ll be looking at the most hilariously bizarre and awkward handshakes of all time. We will only be including traditional handshakes on this list, so, for example, that time Ryan Seacrest tried to high-five a visually impaired man will not be included.

#10: Conan O’Brien & PewDiePie

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Back in 2016, famed YouTuber PewDiePie visited “Conan” to play and promote the video game “Far Cry Primal.” After Conan kills a man in the game, he goes in for a bizarre mixture of a high five and a handshake. It starts with what looks like a high five before quickly transitioning into a handshake. Unfortunately, PewDiePie is still in high five mode and fails to adapt to the change in hand placement. The results were quite awkward, to say the least. Not one to let an awkward situation slide, Conan comments on the “awful” highshake and claims that he never wants to do that again. We don’t blame him.

#9: Shinzo Abe and Xi Jinping

Now here’s a handshake where the awkwardness is not so much in the physical act itself, but the whole situation . . .not to mention that it happened on the world stage. In 2014, Chinese-Japanese relations were, shall we say, not all that good. And that is hilariously manifested in this supremely awkward handshake where Japan’s Abe is not only forced to wait for Xi Jinping to mosey on over, but the Chinese leader doesn’t actually respond to Abe or utter a syllable the entire time. That is some seriously cringey geopolitical drama right there.

#8: “Definitely Not Awkward Here”

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Professional gaming tournaments are a goldmine for awkward handshakes. Case in point - this bizarre handshake from a tournament in Australia. Despite the announcer asking the contestants to shake hands, they seemingly can’t commit to the act. Their hands hover within inches of each other and fail to connect for a solid five seconds, almost like there’s a force field preventing them from touching. One of the men even goes in for a backwards handshake with his left hand! The announcer can only look on in complete bewilderment. As do we.

#7: Green Jacket Ceremony

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Golf is a very professional and courteous sport, and it favors gentlemanly conduct above all else... which makes awkward situations like this even more awkward. PGA golfer Bubba Watson won the Masters Tournament in 2012. It’s just too bad that the height of his professional career was marred by such a cringey handshake! As he stands to receive the green jacket, Chairman of the Augusta National Golf Club Billy Payne goes for a handshake. However, he lowers his hand at precisely the wrong time, forcing Watson to deke Payne and go left. Payne can only stand there and scratch his nose in embarrassment.

#6: The Double Left Hanging

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Daytime television is great. You never know what you’re going to see! And sometimes that includes a rare double left hanging. After Christopher wins the showcase, host Drew Carey goes in for a celebratory handshake. Unfortunately, Chris is too busy celebrating to notice. He realizes his mistake and goes back for a handshake, but at this point Drew is too busy hosting to acknowledge his incredibly awkward and hilariously prolonged attempt. You have to hand it to Christopher - the man is committed to honoring a handshake!

#5: Kevin Love’s Freethrow Handshake

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It’s customary for basketball players to give a little handshake or a brief touching of hands after each free throw attempt. This custom resulted in a very funny interaction between Timberwolves players Kevin Love and Wesley Johnson. Johnson goes for the handshake, but Love is late in reciprocating. Johnson gives up and walks away, but Love is dedicated to getting his handshake. He follows Johnson like an obedient dog, all while Johnson enticingly wiggles his fingers. They finally connect, but Love had to walk what seems like miles to get there.

#4: Joseph Gordon-Levitt & Stephen Merchant

There’s nothing more embarrassing than missing a handshake in front of millions of people! While appearing on “The Tonight Show,” guests Joseph Gordon-Levitt and Stephen Merchant took on Jimmy Fallon in a lip syncing contest. Levitt loved Merchant’s performance and went in for a congratulatory handshake. Unfortunately, Merchant had turned towards the audience and didn’t see Levitt’s outstretched hand, effectively leaving him hanging on national television. We don’t know if that was unintentional or a secret power move on Merchant’s part...

#3: Literally Dragged Offstage

It’s nice to know that even world leaders can’t get the handshake down. In 2015, we received one of the most awkwardly hilarious handshakes of all time between Hungarian Prime Minister Viktor Orbán and former President of the European Commission Jean-Claude Juncker. After a successful and totally not embarrassing handshake, Orbán...forgets to let go. Either that, or Juncker refuses to release him from his grasp! Either way, the handshake ends with Juncker quite literally dragging Orbán out of the room. He looks like a child crossing the street with his dad. But hey, we all have our childish instincts.

#2: Donald Trump & Shinzo Abe

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Donald Trump is well-known for attempting to intimidate people with powerful and prolonged handshakes. He’s done it with Emmanuel Macron, and he’s certainly done it with Japanese Prime Minister Shinzo Abe, who seems to have a knack for being involved in awkward handshakes. The latter incident was especially eventful and newsworthy thanks to its epic length. During a photo op at the White House, Trump and Abe shake hands for an astounding, and frankly unbelievable, nineteen seconds. If that isn’t awkward enough, Trump continuously yanks on Abe’s hand and awkwardly pats it on two separate occasions. When it’s finally over, Abe looks away with a very telling face. You can practically hear his internal thoughts screaming, “Well that was weird!” Before we unveil our top pick, here are a few honorable mentions. John Key Double Shake Gary Neal’s Invisible Handshakes Here’s the Mic

#1: Barack Obama’s Awkward Arm Raise

President Obama was at the forefront of some truly disastrous handshakes throughout his political career. Who can forget that peculiar three-way handshake between himself, Justin Trudeau, and Enrique Peña Nieto? Or the other three-way handshake between him, Shinzo Abe (him again!), and Tony Abbott? But absolutely nothing beats the handshake-turned-arm raise with Cuba’s Raul Castro. There’s just so much wrong and funny about this, from the unorthodox arm raise itself to the hilariously limp way that Obama’s hand dangles from Castro’s grasp. Turns out handshakes are harder than we all thought.

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