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11 Times The 2016 Presidential Candidates Tried Way Too Hard To Prove They're Cool

These efforts to be Down With The Kids resulted in some hilariously epic fails this year.

Most of the 2016 presidential candidates have made it pretty clear that they'd do just about anything to convince us they're cool in an attempt to get at our sweet, sweet Millennial voting block. (Although at least one of them also apparently couldn't care less.)

Much of the time, those efforts have resulted in utter and complete failure, much to the collective delight of the Internet. Here are 11 of our favorite fails from 2015:

  1. That Time Jeb Bush Didn't Understand How Hoodies Work

    "Jeb! Bush is a Very Cool Candidate™ who knows what it means to appeal to The Kids. And The Kids just love it!" Esquire writer Jonathan Evans joked in October when this video surfaced. "So what's a swag-ass 62-year-old politician to do, in the face of Internet-addled, severely decreased attention spans? How can even a Very Cool Candidate™ like Jeb! maintain his favorable estimation in the eyes of The Kids? By donning their customary garb: the hoodie."

    Unfortunately, despite the fact that he has a creepy-ass Super PAC of Millennial "fans," Jeb doesn't seem to realize that hoodies have zippers, and that it's not customary among The Kids to put on a zippered hoodie by awkwardly wrestling yourself into it while it's still fully zipped.

  2. Hillary Clinton's Emoji-Speak Fail

    Lots of politicians have had a hard time mastering Twitter, and Hillary is no exception. After her campaign tweeted, "How does your student loan debt make you feel? Tell us in 3 emojis or less," Twitter was pretty universally unimpressed. The response included everything from jokes about Clinton's incorrect grammar (it should have been "3 emojis or fewer") to sincere clapbacks like, "3 emojis can't begin to explain the pain of $200k in student loan debt."

    News outlets quickly declared that her attempt to connect with Millennials by speaking in their newfangled emoji-language had totally failed . At least Hillary had a sense of humor about it.

  3. When Bernie Sanders Posted Instagram Pics Of His Lunch Date With Killer Mike

    Okay, this one might actually be a little cool. According to the Washington Post, during Sanders' November trip to Atlanta, he spent a day touring the city and eating soul food with the Run The Jewels rapper, who officially endorsed the Vermont senator at a rally later that night. Plus one for Sanders. He still looks deeply dorky (not to mention tiny) next to Killer Mike, though. (To be fair, who wouldn't?)

  4. Rand Paul's Weird Obsession With Ray-Bans

    Rand Paul really loves Ray Bans. Like really-really. In addition to rocking them in public every chance he gets, the candidate also branded a bunch of Wayfarers with his campaign logo and started selling them without Ray-Ban's permission -- which Ray-Ban was decidedly not down with, and was quick to shut down.

  5. Martin O'Malley's Truly Terrible Rendition Of 'Bad Blood'

    Following his failure to wow anyone at the Democratic debate in October, O'Malley -- who, weirdly enough, is also the frontman for a Celtic folk rock band -- showed up at "The View" with his acoustic guitar in tow and performed an awkwardly dad-tastic rendition of Taylor Swift's summer hit.

    "Katy Perry, I'm told, is doing like a benefit concert for one my opponents in Iowa, so in response I thought I'd offer this up," O'Malley said. Guess no one told him that Perry-Swift beef probably wasn't even real.

  6. When Ted Cruz Did A Bunch Of God-Awful 'Simpsons' Impressions

    Cruz collaborated with BuzzFeed in June to create a god-we-hope-this-goes-viral video of the candidate "auditioning" for the Simpsons following the news that voice actor Harry Shearer, who voices many of the show's most-beloved characters, was leaving the show. Cruz's impressions were so awkward and cringe-inducing that even Jon Stewart weighed in: "That's the weirdest f-cking thing I've ever seen," he said. "Normally you have to wait until you're actually President to do that much damage to something America holds so dear."

  7. That Time Ben Carson Tried To Prove He's, Like, Totally Down With The Rap Musics

    In November, the Carson campaign released a radio ad featuring what Vice editor Drew Millard referred to as, "lyrics that only a true Republican could construe as rapping." The rap included verses like, "If you wanna get America back on track / We gotta vote Carson, matter of fact!" and "Vote and support Ben Carrrson / To be our next president it'll be awwwwesome!" The ad only aired in cities with large black populations, including Detroit, Atlanta, Houston and Memphis, and the Carson campaign was criticized for assuming that appropriating hip hop (poorly) would be enough to convince young black voters vote for him.

  8. When Marco Rubio Kept Insisting He Loves The Wu-Tang Clan But Couldn't Name A Single Member

    During an interview with Fox News in June, Rubio said he loves Wu-Tang Clan, but when asked whether he had a favorite member he stammered, "No. You know, I don't know." The host said, "You can't pick a favorite?" To which Rubio answered, "No. That's like... you know, uh, that's like early '90s stuff."

    It was the second time the candidate had insisted he likes Wu-Tang but then declined to name a single member. Rubio has also made several other embarrassingly failed attempts to prove just how much he loves the raps -- including claiming to love Pitbull.

  9. Donald Trump's Cringe-Inducing High-Five Fail

    Reddit user basilect posted this hilarious gif of Trump awkwardly attempting to high-five Ben Carson during the Republican Debate in October with the caption, "Donald Trump Tries To Show His Black Friend How Cool He Is." Trump grins at the camera proudly during the awkward, fumbling hand-grapple, while Carson appears to be un-amused.

  10. That Time Carly Fiorina Ripped Of Back To The Future -- Poorly

    In a bizarre attempt to capitalize on all of the buzz around "Back To The Future" day in October, a Carly Fiorina PAC made a really bad parody video with an actor pretending to be Doc Brown. The writer of the films was not a fan -- so much so that he brought legal action against Fiorina's campaign.

  11. When Chris Christie Betrayed Bruce Springsteen By Declaring Bon Jovi His True Bae

    It's well known that Chris Christie is totally obsessed with Bruce Springsteen, but when the New Jersey governor was asked whether he prefers Bon Jovi or Springsteen during a July interview, he metaphorically stabbed his idol in the back by stating that he now prefers Bon Jovi.

    His wife said it first -- which makes it look an awful lot like an embarrassing case of succumbing to peer pressure. He later tried to clarify the flip-flop by claiming he meant that he likes Bon Jovi better as a person because they're such good buddies, but he still likes Springsteen's music the best. Sure, Christie. Sure.