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The idea of cringe is ancient, but the age of social media has instilled it with new meaning. We are all artists and authors of ourselves. We have the power to present our lives to the world however we deem fit. Some of us have a preternatural compass governing this presentation. We give just enough of ourselves away to keep our followers engaged while maintaining a patina of well-adjusted cool and considered stability. Some of us are effortlessly smart and funny, needing minimal characters to convey our intelligence and wit, firing off takes as the daily news unfolds online and in our lives. Some of us can navigate being intimate with our followers, we share our trauma, our hottest takes, but are able to maintain a tone of thoughtfulness, righteous anger, and a truth to power quality that rockets some accounts to prominence.
Of course, some of us lack this compass. Some of us occasionally make mistakes. We are reactionary, quick to anger, we come across as dull or insensitive, we alienate and turn people off. As a person who’s been writing on the internet for many years, I myself have more than a few pieces I wish I could take back. And this is why I have sympathy for embarrassing rap songs.
If music was sign language, rap music would be a tightly balled fist. It’s a genre that has always been about outward strength, presenting it to the world and vigilantly preserving its presentation. It’s a music that was born in dire circumstances, in brutal environments all over this country, and the artists who have practiced it throughout its history predominantly came from similarly ravaged places. Accordingly, there’s a kind of logic in rap’s reluctance towards showing vulnerability. It’s a music made by people who were raised to understand the mortal danger of revealing weakness of any sort.
But music is a creative medium. It’s a shark, and a stagnant shark is a dead one. It demands progress, and you can’t blaze a trail without searching for one. The magic of discovery is actually a science that relies on experimentation, and experimentation requires creativity and fearlessness. A monotonous tone, a rote swagger, a mean mug, can’t be all there is to this forever.
Throughout the history of rap, we’ve seen some of the genre’s bravest souls strike out in search of something bold and new. This could extend to playing with literary devices, trying out new flows, or taboo subject matter. Perhaps they’ll dabble in a genre that rap was previously not comfortable with, and you get a paradigm shattering classic like Run DMC and Aerosmith’s “Walk This Way.” Or perhaps they dabble in a genre rap was not previously comfortable with, and you get a bag of rancid Canal Street garbage like Puff Daddy and Led Zeppelin’s “Come With Me.”
The truth is, the margin between an open hearted, aching and brilliant song like Ab-Soul’s “Book of Soul,” and an off-putting tell-all like Cam’ron’s “IBS” is razor-thin. Both songs open up to their listeners, relating personal pain, presenting their artists naked and without defense. The difference is one is about a history of tragedy related by a poet on the verge of breaking down, and the other is about how Cam’ron occasionally shits blood. Both songs probably seemed like good ideas at the time, and, I would guess, both men were surrounded by people there to affirm their every creative impulse. At some point, they took a deep breath before submitting the track to their label, and simply decided, “fuck it.”
That’s why many of the songs on this list are by some of the greatest rappers in the history of the medium. By no means is this a list of “bad” songs. Perhaps ill-conceived, or poorly executed, but not strictly bad. It’s a special type of bad that merits distinction. Think of rapping like playing darts at a bar. Most of the time, a good rapper hits bullseye. But if you throw enough darts at the board, eventually you may get bored or distracted, restless, and maybe an opponent blows in your ear as you’re about to release, and the dart goes way left and buries itself in some burly goateed trucker’s ass; then he marches over in a sleeveless flannel vest and a mesh camo hat and rinses you in front of your girl and all your friends, and throws you into a mud puddle. That’s basically the equivalent of what happened when Lupe Fiasco decided “Words I Never Said” was ready for us all.
But even Lupe deserves our respect, nay, our admiration. So many rappers, even ones who get lucky and find a moment, will make their money and pass through the corridors of time into obscurity. They exist in the now as temporal radio hour filler, merely tolerated as they make pleasant, disposable elevator rap, before dissolving into history, remembered by few and loved by none. And some will live on in their music, much of it great, brilliant, and historically important, with a few absolutely awful, hilarious, and yes, cringey articles sprinkled in between.
What I will take from this list is, in music, as in life, sometimes you need to have the courage to hit send, but every once in a while, you need the presence of mind to take a moment, assess what you’re trying to say and why you’re trying to say it, and probably delete.
*Honorable Mention: Lil Wayne- Mrs. Officer
Man. Fuck this copaganda and the corny, annoying ass Bobby Valentino hook it rode in on.
30. The Cocoa Brovaz ft. Raekwon – “Black Trump”
Guessing Smif-n-Wessun would take this one back if they could.
References can be unforgiving. No telling what a random name check will go on to become, or these days, what old tweets they may have lying dormant like undetonated landmines. The Cocoa Brovaz can be forgiven for naming this fucking jam after what seemed like a fairly harmless avatar for institutional wealth, influence and power in the late ’90s, unaware he would eventually become the least likely and (arguably) most toxic president we’ve ever had. Then again, Trump had shown his whole ass to us over and over again prior to this dropping in ’98. In retrospect, while we can’t blame anyone for not predicting this asshole would be president, words mean things. Be selective in your metaphors.
29. Wu-Tang Clan – “Black Shampoo”
In 1997, burgeoning lotion and oil purveyor Bath & Body Works approached Rza as part of a concerted attempt to diversify their market share. They wanted to plant product in the Wu-Tang Clan’s sophomore effort, Wu-Tang Forever, and they did, with U-God’s solo masterpiece, “Black Shampoo”, a song that is basically a list of things you could buy at the store and rub all over your girl while you make love to her in the shower, or something. Of course, I’m kidding. Or am I?
This one is off for several reasons. It completely throws the vibe of Rza’s double album opus, a grim and cinematic artifact of late 90s East Coast boom bap which took the aesthetic the Clan had consecrated through its first generation of albums and muddied it. This may very well be the softest song in the entire Wu-Tang oeuvre up to this point, and it’s U-God drawing a bubble bath for his girl?
All I’m saying is, if you happen to ever find yourself in U-God’s bathroom, and the medicine cabinet looks like this, don’t be surprised:
28. Akinyele – “Fuck Me For Free”
Akinyele is a great 90s rapper who has sadly, more or less been lost to history aside from “Put It In Your Mouth” (outside the circles filled with old obsessive rap nerds like me). Perhaps it has something to do with the fact that he was probably the raunchiest rapper who ever lived. He had a great ear and made great, anthemic songs, but they were all songs that wouldn’t allow for eye contact with another human being on the elevator in your building if you were listening to Akinyele on earbuds.
“Fuck me For Free” is case and point. It does the admirable work of making Akinyele sound cheap, AND like he often pays for sex. Also, if you watch the edited version video, “Love Me For Free”, there’s a whole color coded pajama motif with Ak and some R&B group called Complexion that I’m guessing he met in a dollar van.
27. Kanye West- “Monster (Jay-Z Verse)”
It’s worth considering why Jay ended up on this list a decent amount, he also had a few other tracks that narrowly missed the cut. Earlier in Jay’s career, like many of his fans, I wanted him to open up more. He had such a puritanically polished detachment in his manicured bars, it gave his music a cold inaccessibility. Even on his confessional songs, you never saw it coming down his eyes. Then later in his career, he really let the emotions fly, and it turns out he was better off in his wheelhouse, firing off brilliant double entendres about selling drugs and shooting people, because the man is just not built in a way that allows him to discuss his inner life without making you want to dive under couch cushions [ed. note: this point is….]
I would say there is no more shame faced, look at the floor moment on this list than when he breaks his flow on this classic posse cut to say “Looooovvvvveeee! I don’t get enough of it” Just sounds like something torn whole cloth from a fourth grade diary.
26. Cam’ron – “IBS”
Who among us hasn’t posted an overshare? Certainly not Cam, who, in spite of the largely non-narrative tethered, wordplay obsessed style he adopted later in his career, took some time out to tell the world a bit too much about his stomach issues.
It’s difficult to put artists like Cam on this list because you get the impression the man has never actually experienced embarrassment in his life. But I wonder if even he looks back at this one and has thoughts. What’s weird about this song is it completely flies in the face of nearly every song he made post S.D.E. Even when he had what felt like personal moments on tracks in the aughts, they all presented the vaseline gloss of gangster cinema. Here, he’s rambling as always, but is direct, vulnerable, uncomfortably descriptive, and feels candid. Interesting that the subject he chooses to explore, in depth with his fanbase, is irritable bowel syndrome.
25. J Cole – “Wet Dreamz”
You ever wonder what the first time J. Cole had sex was like? Me neither!
I get in, or used to get in, a lot of bar arguments with young people over J. Cole. There’s some kind of They Live filter hip hop fans born after 1990 are cursed with that doesn’t allow them to see this guy’s face is a naked skull with creepy googly eyes bulging out of the sockets. Well, here is the case in point.
The beat is classic J. Cole: a boring and inert copy of 9th Wonder copying Primo. Or maybe Just Blaze or Kanye copying Primo because this whole album sounds like J. Cole got wasted, listened to Tha Game’s The Documentary at three o’clock in the morning, ate a few very old slices of uncovered pizza with troubling growth on them languishing in an undisturbed back corner of his fridge, and violently shit this out the next day.
The concept and execution seems engineered for 106 & Park, and I don’t think it’s a coincidence that 106 & Park was cancelled a few months after this dropped. It’s cheesy and lazy, sounds like a vastly inferior version of fourteen other concept songs about young love that preceded it, and features a video where two dogs of different breeds are carrying out mating rituals with each other. Almost as disturbing as it is bad. Not entirely sure if this is ranked high enough, or low enough, you know what I mean.
24. Busta Rhymes – “Arab Money”
Sigh. Ah, racism. This was a late period hit with multiple remixes for Busta because it was seen at the time by some as a goofy, harmless “model minority” type of concept, with the gag being Busta and Spliff are as rich as Middle Eastern oil barons. Of course, the song was also extremely controversial and offensive, sprinkled with Arabic and in the video, visuals that fetishize and exoticize moneyed Arab culture to the point of dehumanization. Ron Browz does Busta no favors with a hook that leans on Disney’s Aladdin and a beat which is also somehow racist.
23. Common – “Between Me, You & Liberation”
Rap is a dynamic medium, so I’m not going to say there is anything it can’t do. Perhaps there is a way to credibly and meaningfully discuss sexual abuse, death, religion, organic medicine, and grappling with homosexual urges on a single song, but this very simply ain’t it.
Common is employing his Def Jam Poetry, Kid Cudi narrator spit, telling Hallmark made for TV stories that wear their pathologies on their sleeves, present no complicating quirks of real life or good writing, and arbitrarily resolve themselves in the span of a bar. The problem is the effort he’s willing to expend. These are not three verses, they should’ve been three songs, hell, with Common, he could’ve made them three whole concept albums. Instead they’re these vague stick figure sketches that clamp your delicates and shock you with a car battery, if car batteries channeled squirm rather than electricity.
The song serves a decent reminder that Common is a clever and decent human being, but whether he’s practicing his front facing Kangol B-Boy shtick, or kicking game to Erykah, or hitting his fight choreo in a John Wick film, he simply can’t help being corny.
22. Eminem ft. Lil Wayne – “No Love”
Three legends for the price of one: Eminem, Lil Wayne, and tragically, Just Blaze came together on this flip of Haddaway’s eurotrash “What Is Love?”, previously and still most famously known as the anthem Saturday Night Live ran into the ground with a skit they turned into a movie. And the beat plays into this. It was a sample that should’ve been left on the table, or satirized by early Em on one of the name checking, dad joke-laden pop singles he used to lead his albums with.
Unfortunately, this song is indicative of late Em, aimed at Z100 over Hot 97, robotic rapping on an overproduced beat, and a autotuned, braying, horribly layered hook that sounds like it was scribbled in the moment on a cocktail napkin and sung immediately following a gargle with broken glass. The verse is his really embarrassing interpretation of rap emo, the perfect soundtrack for cutting your forearms on a tile bathroom floor, and for literally nothing else.. The less we say about Wayne here, the better.
But somehow, the brilliant and nearly career perfect Just Blaze takes the worst beating here. He definitely secured the bag, but this bangs like every drum kick marks the selling of his soul. This is the worst beat he ever made.
21. Puff Daddy – “Come With Me”
*Bob Saget Voice* Kids, in the Summer of 1998, Puff Daddy was at the apex of his career. He had released an incredible solo album in the wake of Biggie’s death, he had a stacked Bad Boy roster, and he was about as close as rap has ever come to a sure thing with his golden ear, consistently picking the perfect old pop songs to rehash, on hit after record breaking hit. And then, he decided it was time to tackle Led Zeppelin’s “Kashmir”, with Jimmy Page himself, as the soundtrack lead single for a stink bomb of a Roland Emmerich Godzilla remake starring Matthew Broderick. It’s a giant orchestral rap opera production, and Diddy is firmly entrenched in his awful, sleeveless rockstar period, shouting all his ghostwritten lyrics in videos with million dollar budgets that could’ve been used to feed and house people. A mess.
20. Limp Bizkit – “N Together Now”
Seeing as how this entire list is me making sport of some of the greatest rappers of all time, it’s only fair for me to tell on myself here. I hated nu metal, but I loved this song. The Primo beat, the classic Meth…… appearance(?), there were a lot of excuses that I willingly made for this trash. Part of what makes things embarrassing is your part in them, looking back at articles of culture and shuddering at what a fucking lame dork with shitty taste you were (and let’s be honest, still are). This song is that for me.
19. Kanye West- “Big Brother”
Some people keep their daddy issues to themselves and some people make epic songs about them. Here, Kanye is all but begging Jay for his approval. A real weirdo. We all have gripes with people, grievances to air, I’m sure. But to do all this as public as humanly possible? The self own about not getting into that show as the man is rapping over your own beats? We should’ve seen his Trump turn coming, because this double down is a move only our former president would be dense and impervious enough to also not recognize as a bad idea.
And to make matters worse, it worked! It’s also horrifically embarrassing for Jay, because some believe as a direct result of this song, they settled their differences and made Watch the Throne, so this song also has that to answer for.
18. TIE: Jay-Z & Chris Martin – “Beach Chair,” “Lost”
My absolute favorite thing about the pointless beef between Kanye and Jay-Z is one of Kanye’s long simmering gripes: that Jay-Z “stole” his idea of making a song with Coldplay frontman Chris Martin, which he actually did twice, in a home and home on his 2006 atrocity Kingdom Come, and Coldplay’s Prospekt’s March in 2008. The union produced two of the worst songs of Jay-Z’s career.
We see Hov, doing his rich guy middle aged raps with gross and saccharine Starbucks hooks from Martin, who I would say was at his nadir as an artist (God knows what he’s up to these days. I certainly don’t), but that would require a peak. These were two moments that served as canaries in the coal mine for Jay, when you had to stop for a moment and grapple with the fact that in the end, time comes for us all.
17. Ice Cube – “Black Korea”
Another example of egregious racism that we just kind of let slide at the time. Cube’s misguided anger wasn’t entirely unfounded. The concept of other races operating businesses in Black communities even as they seemed to openly resent the clientele they were exploiting was a hot button issue at the time, explored explicitly in Do the Right Thing.
Death Certificate dropped in October of 1991, seven months after 15-year old Latasha Harlins was murdered in a bodega by a 51 year old female Korean owner, who was let off with time served. But it’s still a pretty inflammatory and fucked up song that does the same thing Cube is accusing his target of: generalizing a large and diverse group of people, projecting the behavior of its worst actors across a broad spectrum, which is equal parts shitty and lazy. Fortunately, this was the last racial and/or political controversy Ice Cube would ever be involved in.
16. Jeru The Damaja – “Can’t Stop the Prophet”
Jeru was emblematic of a genre of hip-hop guy that was prevalent on the east coast in the 90s. This symbolic dude (always a dude) made distinctions between rap and hip hop, Biggie and Jay-Z were too mainstream due to the materialism in their frivolous bars, he was probably a five percenter, and nothing on this Earth was more important to him than the sanctity of his own very narrow definition of hip-hop. This imagined guy’s favorite rapper was Jeru The Damaja.
On this song, Jeru is completely arrhythmic and doesn’t rhyme, and it’s this story packed with tortured metaphors where Jeru is a superhero who fights anthropomorphic negative emotion supervillains like Anger, Ignorance, Fear and Animosity (wielding pork chops and barbershop clippers as weapons) with math, science and education. Ironically, the world’s dumbest song.
15. Nas – “Who Killed It?”
Nas delivers this entire song in a nasal, out-the-side-of-his-mouth, James Cagney/Edward G Robinson old timey gangster voice. The song is dense, and if you absolutely must get on the wavelength here (can’t recommend that), some of the allusions are clever, but it’s essentially Jeru’s humorless, reactionary critique with noir dressing.
In later interviews, Nas revealed the genesis was a bit, a voice he would perform in the studio (perhaps inspired by this?) that he was fucking around with and decided to record a track practicing it, then, incredibly, threw it on Hip Hop Is Dead. When you consider the more out there shit in the middle third of Nas’ catalogue, there are many lessons to be learned concerning how to create and innovate without veering into cringe. As we will soon discuss, some of Nas’ concept work is among his best (See: “Rewind”, “One Mic”, “Where Are They Now”, “Sly Fox”, “Sekou’s Story”, most of the Distant Relatives project). But when he bricks he bricks hard (“Undying Love”, “Dr. Knockboots”, anything about Kelis and most of Untitled).
Some give Jay-Z shit for his calculated legacy building through The Black Album, but in some respects you have to give him credit for the obvious thought and care he’d put into every track on his albums and every guest appearance. There’s this casual, tossed off quality to Nas’ later work. Once he had to rush a second draft of I Am to market and shit the bed with Nastradamus, a realization that he’d never get back to Illmatic seemed to creep into his work. In some ways it was freeing for him and opened up his pretty grim and serious music to surprising and genuinely innovative experimentation, but it also forced his fans to strain to defend garbage like this after ecstatic first listens.
There’s a possibility Nas just has terrible instincts, as evidenced by his famously awful ear, and the fact that his Lost Tapes series eclipses several of his actual albums. But as alluded to in the aforementioned interview, he really just comes off as careless, not interrogating his choices and unwilling to kill his darlings, and what you’re left with is unfortunate shit like “Who Killed It?” In this case, you did bud.
14. Machine Gun Kelly – “Lonely”
Folks, I told you before that this collection of songs aren’t necessarily “bad” in the
traditional sense of the word, but this Blink 182 song by future hip hop youth pastor Machine Gun Kelly absolutely is. It’s the worst song on this list, and also the worst song ever made. It’s about how everyone in his life leaves him or dies, presumably to get away from him, and you very quickly empathize with all the other people.
The only reason it lands here is because MGK is a hack and should be immune from lists like these, as making bad music is his raison d’eter, but even for him, this is a bridge too far.
13. DMX – “How’s It Goin Down”
I’m as disappointed to see this Middle School Dance classic here as I imagine you are.
And the horror of this completely blew past me at the time, but as an older person with a daughter, the line “54/11 size seven in girls/baby face, but look like she was 11 with curls” is absolutely bone chilling.
12. KRS-One – “Nas Tribute”
A real “Jordan on the Wizards” situation. Nas’ Street’s Disciple is one of my favorites from the back half of his catalogue. It’s overstuffed with ideas (a few of which were in contention for this list), and one of the most successful is “U.B.R.”, a rapped biography dedicated to his hero Rakim. At the end of the song, Nas suggests that it’s part one in a series of biographical homages he will begin throwing on his projects, with the next going to KRS. However, two years later, there was nothing of the sort on Hip Hop Is Dead.
KRS-One, an actual legend and one of the most important rappers of all time, has not exactly aged gracefully as an artist over the last 20 years. This is exhibit A, one of the thirstiest songs I’ve ever heard, just openly sweating the rapper nearly 10 years his junior. I think the idea is that he’s practically begging Nas to make the song he teased. While Nas’ tribute to Rakim was a researched and well composed career arc with a narrative, KRS just kind of rambles, giving Nas praise for vague accomplishments like “bringing hip hop back from the dead”, “bringing Queensbridge back”, making Chris’ home burrough of the Bronx “lean back”, etc. It was a bad look, but what made it worse was Nas left him on read.
11. Lupe Fiasco – “Words I Never Said”
Lupe Fiasco delivers a real gem of dumbass opinions on this flaming bag filled with dogshit, left on America’s porch. Lupe brags about not voting for Obama, calls out easy targets like Israel and Glenn Beck, pats himself on the back for his fearless truth telling, and gives us a few half facts he pulled from a used book he skimmed off a Black Isrealite’s folding table on Court Street. Nothing he says is exactly wrong, but the Facebook comment thread politics here are a mile wide and an inch deep. I too was once a sophomore in high school, Lupe.
10. Canibus – “I Honor U”
A lot of decisions were made here. I have to believe infamous late 90s battle rap legend Canibus was getting high on his own supply when he made this stupefying concept song. In it, in his overeducated, hyper articulate, syllable packing style, he recounts his mother meeting his shitty father and physically being conceived, then follows the trajectory of his young self as a sperm, tracing his path through developing as a fetus, to birth. What’s more incredible is this song was a single, had a video, and was a minor hit off Canibus’ debut album.
9. Talib Kweli ft. Res – “Idle Warship”
Google “Talib Kweli Res,” click around for a bit, then watch this video.
8. Dead Prez – “Mind Sex”
A tough one for a group I will always cape for. This so unwittingly captures a Type Of Guy I came across far too often in my early 20s, who thought an ancient grain salad and chess as foreplay made him seem worldly and different, but he probably overcooked the grains, overdressed the salad, and sucked at chess. Really just the absolute worst.
7. Logic- 1-800-273-8255
I would imagine making a burn list like this opens me up to accusations of being heartless, or just mean, and this would probably be the song on this list you could point to if you wanted to level that accusation. Suicide and mental illness are no laughing matter, and all you need to do is scroll down on the YouTube video’s thread and read thousands and thousands of comments written by people with awful taste in music who this song really helped. Here’s the thing, I like plenty of young emo rappers like Rod Wave, who communicate pain and sadness and depression in near biblical terms that carry real weight and scratch an ancient itch relatively new to rap in this wounded, devastated form.
So I feel qualified to say, “I get it,” but this song still blows. Just because it has a weighty subject matter, and has a therapeutic quality for some people who need it, doesn’t mean we can’t consider it with a critical eye, and sorry, but it’s fucking awful writing. There’s nothing remotely subtle here, it’s a laundry list of petulant whines that doesn’t really go far enough if he’s attempting to voice a person legitimately thinking about killing themselves (“Nobody calling my phone.” So you’re going to kill yourself? Really, Logic?). Also, Matthew Modine plays a homophobic dad in the video. Maybe I’m just an old man who is dead inside, but this song is supposed to prevent people from wanting to kill themselves, and it has the complete opposite effect on me.
[Ed. Note: Suicide is a very serious matter, and we commend you if this song helped quell your suicidal thoughts in any way. If you are someone you know are thinking about ending your life, please call, ironically enough, the number listed as the song title here: 1-800-273-8255.]
6. Meek Mill – “Wanna Know”
Bad disses are the worst, but this failed hit on Drake is worse than bad. Meek was dating Nicki Minaj at the time, and I’ve always suspected he pulled some punches on this because he wanted the press, without starting a real war. I mean it’s Drake, an abjectly hilarious guy an even mediocre rapper could find a million things to take issue with, and this is fire breathing Meek at his peak. This couldn’t possibly have been the best he could’ve done. My evidence is most of this beef occurred on Twitter. Soon after the Tweets, Meek apologizes to Nicki for the Tweeted shots he took at Drake, kind of giving up the game before it really got rolling.
Drake hit Meek twice, with the somewhat lackluster “Charged Up,” followed by the devastating “Back to Back”, which got nominated for a fucking Grammy. “Wanna Know” was Meek’s eventual response, a turd that sunk quietly and no one but me remembers. Soon after, Nicki dumped Meek, Meek went to jail, and his career has never really recovered. One of the all time Ls any rapper has ever taken in battle.
5. B.O.B. – “Flatlines”
One of my favorite bits when one of my friends starts to go out there with some absurd and far fetched plot they believe is happening in their lives or in the news, is to begin breathlessly recounting lizard people theory and the temperature steel beams melt at. The heart of the joke is there’s just something fucking goofy about tin foil hat YouTube documentary shit. It’s a willingness to take Occam’s Razor and huck it out the window with great force, a complete and total destruction of logic and reason. Kyrie Irving’s favorite song is this joint that is all about the Earth secretly being flat. Time to log off, Bob.
4. Wale – “Rather Be With You”
Some days, I think the extended metaphor is the worst thing that ever happened to rap.
It has produced some of the dumbest ideas and worst songs that have ever passed through the medium. This one is special though. Rather than just settling for objectification, the super friend morons Wale and J. Cole (and my guy Currensy) team up to disembody the vagina and make a bunch of dumb jokes, referring to it as a person: “Don’t make a grown n***** beg that ain’t fair bitch/just take them clothes off, oh look you got your hair did” — Poet Laureate, J.Cole.
3. Andre 3000 – “My Favorite Things”
I have a single, retired Aunt who had a 65th birthday party a few years ago. She rented out an event space in Rockland County, invited all her friends and family, and the centerpiece of the party was an acoustic guitar recital that lasted somewhere between 40 minutes and five years. She had taken up guitar lessons post retirement and wanted us all to hear her progress, playing some standard compositions with no singing or accompanying music or anything.
Also, on the last proper Outkast album, Andre made the mind boggling decision to include a five minute trip hop tribute to Coltrane with his cover of “My Favorite Things”. Dre apparently did the manic drum programming on it, probably the worst part of the song, which I consider one of the most indulgent moments ever on any major rap album. The point of both anecdotes is simple: Sometimes, best to just keep some things for yourself.
2. Jay-Z ft. Beyonce – “Family Feud”
Welp, take it from me, when you’re married, particularly with kids, you get in fights with
your wife now and then. There’s a few little tricks I’ve picked up over the years to coax my partner off the ledge. You can get flowers or jewelry, but that’s hack, and frankly, if you’ve been married a while, it won’t work. I recommend setting up a date night, coupled with going the extra mile with the kids and with chores and housework, don’t call too much attention to it, just do it, trust me, she’ll notice. And if all else fails, write a short film with Ava Duvernay she’s also directing, get Michael B. Jordan, Jessica Chastain, and Thandie Newton to star in it, and slot in a really bad song airing your dirty laundry and half apologizing for your fuck ups. Unclear if the last one will work for everyone, but I guess it worked for Jay-Z’s business partnership with Beyonce.
1. Kanye West ft. T.I. – “Ye vs. the People”
I’ll be honest. When I was about halfway through compiling this list, I got nervous. It’s massive and wildly ambitious, and left me with an incredibly difficult task: I needed to land the plane with the most embarrassing rap song ever written. It couldn’t be arbitrary, or even debatable. I needed to find something so cringe, so fucking terrible, that every single reader, regardless of issues taken with the rest of the list, would have to solemnly nod their head and acknowledge, “Wow. That man is absolutely right”. I struggled with some of the inclusions on the list and their order, but when I pulled this one, there was never a doubt.
For the uninitiated, this song is a back and forth between Kanye and T.I. (AS THE PEOPLE.), debating his support of Donald Trump. If you haven’t suffered a massive head injury, you’re supposed to agree with T.I., but spoiler, you won’t! Because as bad as that concept is, the puerile execution is even worse. Everyone loses. What I enjoy about the internet is the banter, the arguments, the exchanges of ideas, so I should theoretically enjoy this structure of a bar argument on wax. But it’s for that very reason I hate this so much. The arguments on both sides are so poorly structured, considered, and delivered, that drunk, sleepless OAN Network talking heads could run circles around these assholes. It critically wounds both men’s legacies. It’s bad for rap, it’s bad for the United States of America, everyone who listens to it is a little worse off after they’re done. It is without a doubt, the most embarrassing rap song ever made.