Picture this: You’re riding the high of finally being in a crowded dive bar again. The drinks are flowing, possibly too much. You just heard someone absolutely nail “Sweet Caroline” on the karaoke stage. Now the DJ is calling for the next contestant. Your friends are egging you on. Your brain is saying no, definitely not, but the five (or was it six?) beers in you are saying yes, absolutely you got this. Stumbling up to the grinning DJ, you tell him to queue up “Where is the Love?” by Black Eyed Peas. A classic. You think: the crowd will love it... As soon as the first verse begins you realize you’ve made a grave mistake. The lyrics are flying by at a speed that isn’t suited for your inebriated state and you barely hold it together until the chorus. But thank God, the bar is joining you for the chorus. You’re saved! That is, until the next verse comes in, and you realize, despite the lyrics appearing on a screen, you know way less of the words than you thought you did, and you’re suddenly floundering, hoping to get to the next chorus. But the crowd’s already bored of you — they turn more than the other cheek — and you ascertain you’re living out the worst karaoke scenario. Exit stage left. Defeated. Don’t worry though, you can avoid this fate. Just don’t sing a difficult song. What makes a karaoke song difficult though? For the 2020 Karaoke World Champion, Garvaundo Hamilton, the answer is pretty simple. “I’d say anything by Whitney Houston, Queen, or Journey. They just require so much from you.” Houston’s “I Will Always Love You” is certainly a great candidate for the most difficult track. In fact, Ranker, a website that allows users to make rankings for any category by voting, places the iconic song right at the top. But the rubric for a karaoke performance is limited to the very specific setting. The Karaoke World Championships judge performances using four categories: voice, technique, artistry, and overall entertainment. Performances at the upper levels of the competition are thoroughly rehearsed and polished, qualities that won’t translate to a bar setting. “I’ve been obsessing about this question ever since you reached out,” Eamon Daly, KJ (karaoke DJ) and founder of Pop Up Karaoke, tells me on a video call. “It’s funny because none of those sort of characteristics like tempo and pitch ever entered the conversation.” BEHROUZ MEHRI/AFP via Getty Images For many KJs and karaoke enthusiasts like Daly, the success of a performance isn’t really about your technical proficiency. “A lot of people that bomb are actually just taking it much too seriously,” says Liz Mason, a Chicago-based KJ and karaoke performer. If you’re going up there to show off that you can hit the high notes you’re going to ostracize a lot of the common, tone-deaf bar folk. So the question is a little more complicated than the Karaoke World Championships would have us believe. Liz agrees. “Nobody’s expecting you to be Whitney Houston or Beyonce so the crowd tends to be forgiving about that sort of thing as long as you give it your best.” Of course, the conventional qualities of a song will lend to the difficulty of a karaoke performance. And personality will only take you so far if you can’t manage an approximation of the melody or stay on tempo. With the help of passionate KJs Mason and Daly, I’ve come up with the most scientific rubric for judging the difficulty of a karaoke bar performance and nominated five of the most difficult and impressive tracks to pull off. For he’s a jolly good fellow effect The key to having a successful karaoke performance hinges on winning over the crowd. An easy way to do this according to Mason is to exploit the For He’s a Jolly Good Fellow Effect. “You want everyone in the bar singing along. You want a sense of community.” “The audience can always tell when someone is singing a song for themselves versus when they’re singing it for the room,” Daly advises. “The best karaoke is when the singer is not saying ‘look at me, look at me’, they’re saying ‘look at us, we’re going to make this big.’” In this way, the Karaoke World Championships’ guidelines line up with standard karaoke. The person that is getting up there to sing a technically impressive and polished song won’t be able to exploit the effect of magnifying the difficulty of the track. Fine line of familiarity An obscure song will be difficult to capture an audience with, and if there isn’t a recognizable hook you’ll get a lot of blank looks. On the other hand, a well-known song might be overplayed and boring. If you aren’t intimately familiar with the dynamics of a popular song, or aren’t bringing something special to it, you risk disappointing, and maybe even pissing off a lot of people. Most importantly, you should not only be acquainted with the song, but it should be your song. Passion for a particular track will outshine any issues you may have with actually singing and will easily win a crowd over no matter what the song is. “I would much rather hear a terrible singer who knows the song inside and out, than a great singer who knows the chorus, because you can tell they’re only there to prove their chops,” Daly says. Mason has similar feelings. “If I can tell you’re a professional singer and you’re ‘slumming it,’ you’re totally uninteresting to me. However, if I see that you’re somewhat of an underdog and you just have a love for a certain song, then I’ll find you much more entertaining.” Ryan Pyle/Corbis via Getty Images Interestingly enough, this helped Garvaundo in his competition last year. “I had my top three songs selected for the tournament based on what people around the world were listening to.” But two weeks out from the submission deadline, Garvaundo contracted COVID. “I was like ‘damn!’ I couldn’t record, I was stressed out, coughing, I wanted to quit.” Lucky for him, the rules of the competition allowed him to submit any video that had been recorded after a certain time frame. So, he ended up submitting, not the most popular or polished song he could, but a home recording of him singing his favorite song “Hallelujah” in his friend’s living room. https://www.youtube.com/embed/21TPNGp8tQM “The song that I was just playing around with, ended up being the most liked, highest scoring song in the competition. I don’t feel like I was the most talented vocalist in the tournament — I don’t have any training, really — but I felt like my voice was unique and connected to people.” Some songs just aren’t made for karaoke Songs with a long instrumental break may induce intense cringing. If you aren’t ready to dance your ass off, or shred some air guitar, any song with a substantial instrumental section will prove a challenge. Daly’s big signifier for the difficulty of a track is its length. “Length is wildly underestimated. In my experience, you can do anything if it’s under 3 minutes and 30 seconds. It’s really hard to ruin a room that way. If nobody gets it, you just blow through it quickly and nobody’s gonna be mad.” For Mason, a lot of tracks with heavy background singing and overdubbing often flops. Many of the karaoke versions of these songs won’t include the background vocals which greatly hampers the enjoyability of its performance. Neville Elder/Corbis via Getty Images The 5 Most Difficult Karaoke Songs Using this landmark karaoke song difficulty rubric, here are the hardest songs to perform...drunk or sober. This certainly doesn’t mean that these are the worst songs to sing. In fact, if you can pull these tracks off you’ll wind up with a bunch of free drinks. They’re high-stakes performances which will be rewarded accordingly. “Whatta Man” / En Vogue (with Salt-N-Pepa) “Everyone thinks they know how that song goes. They don’t,” Daly says emphatically. “They only know the chorus. Everybody tries to sing it though, and every karaoke regular sees that and thinks, ‘oh man’” “Whatta Man” is quite the doozy in terms of length at almost five minutes long. The verbose and charisma-dripping verses performed by the legendary rap trio Salt-n-Pepa are difficult to pull off, especially as a one-man show. Don’t be fooled by the straightforward chorus. “Sweet Child of Mine” / Guns N’ Roses Although the singing isn’t technically difficult, Axl Rose’s unique vocalizations are hard to match. But the most glaringly difficult part of the nearly six-minute track is the fact that Slash comes in to interrupt you with a guitar solo every verse, one of which takes up almost half the song. That is of course followed by the repetitive “Where do we go now” section. And if you aren’t ready to fully commit to that, then prepare to answer Axl’s question: you go home. “Bohemian Rhapsody” / Queen It kind of seems like every time I’ve gone to karaoke someone tries this one, and I’ve almost never seen it succeed. It is, of course excessively long at around six minutes, includes multiple long instrumental passages, and, worst of all, the karaoke version almost never has the backing vocals during the crucial operatic passages. Be aware that most people in the bar have heard this song performed dozens of times, and poorly, and it will take something particularly special to get people on your side. Otherwise, when belting “I'm just a poor boy nobody loves me,” remember, you’re that little boy who the crowd does not love. “Total Eclipse of the Heart” / Bonnie Tyler “It’s so overdone. I’ve never seen anybody do it compellingly,” says Mason. This slow and melodramatic Steinman track requires a certain self-awareness to pull off in a bar. If you don’t pull this off, you might see some heads nodding into their beers. Not to mention the dreaded instrumental breakdown and five-minute-and-change run time. “American Pie” / Don McLean First of all, it’s over eight minutes long. Come on, let some other people sing. But also, everyone knows this song. Sure, you might be able to get some of those good ol’ boys drinking whiskey and rye to join in on the chorus the first or second time. But the fourth and fifth? Also, maybe you know the verses, but you’re probably the only one in the bar, so good luck. A poor performance might mean this'll be the day that you die...on stage.