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10 Rap Songs Overdue for Retirement

From Macklemore's "Thrift Shop" to Kanye's "Gold Digger," here are 10 rap songs we need to retire for good.

For most people, the arrival of retirement is a welcome respite from the soul-crushing monotony of their daily routines. For others, it’s a sobering reminder that the ill-advised timeshares they invested in during their midlife crises cut significantly into their poorly managed retirement savings. For yet a third group of people, it’s a dreaded sign they have officially outlived their usefulness as productive members of society. 

With few notable exceptions, nearly everyone has to retire eventually. Trying to fight retirement is like trying to fight the bouncers at a bar: you’re inevitably going to fail and you’ll only make yourself look undignified in the process of being body-slammed by a 300-pound man. Knowing this, you might as well accept your fate and bow out gracefully before you’ve outstayed your welcome.

In a perfect world, this guideline would apply equally to culture as it does to people in the labor force. Unfortunately, culture just doesn’t operate on the same timeline as careers do. Whereas there are memes that become unbearable within a week, there are other bodies of work that manage to stand the test of time for decades on end. How else can we account for the fact that Beyoncé and JAY-Z’s collaborative album, EVERYTHING IS LOVE, took all of a month to leave the cultural consciousness, while the 1999 song “Mambo No. 5” will apparently live on in our minds forever?

Though they no longer have anything to offer from a cultural standpoint, many songs remain a fixture within the popular zeitgeist, taunting us with their lasting ubiquity. Any earworms that once burrowed themselves in our heads have been killed by excessive repetition. Any lyrics we once found clever have been sapped of all of their novelty. All that remains are song-like vessels—like Bruno Mars’ “Uptown Funk”—which unceremoniously trigger the brain’s capacity for recollection, not unlike the feeling of remembering your email password.

Given that rap music is now indistinguishable from popular music, many of the songs that match this description incidentally happen to be rap songs. Certain that you must have noticed this phenomenon too, I put together this list of 10 of the most noteworthy examples so that we can hopefully say our final goodbyes to these outplayed songs forever.

DJ Khaled — "All I Do Is Win" ft. T-Pain, Ludacris, Snoop Dogg & Rick Ross

In 2013, President Obama used this exhausting pep rally of a song as the introductory music for his speech at the White House Correspondents' Dinner. As far as I’m concerned, once a rap song has been deemed tepid enough to be broadcast on C-SPAN at an event filled with Republican lawmakers and Fox News commentators, the public must be forcibly prevented from playing it as if it’s some sort of exultant anthem. No one is voluntarily getting turnt to “Hail to the Chief,” and therefore no one should voluntarily be getting turnt to this song either.

OutKast — "Hey Ya!"

Did you know that when you buy instant-print cameras, they come with an explicit warning not to “shake [your photos] like a Polaroid picture?” OutKast’s “Hey Ya!” was such a cultural phenomenon that it caused the general public to completely misunderstand the basic operating mechanics of a household device. 

Unfortunately, this immense popularity came with a downside. Being the cultural juggernaut that it was, “Hey Ya!” became one of the first songs to attract the attention of the acoustic guitar-playing YouTube cover artists who rose to prominence in the late aughts. If there was any mercy in this world, this song would have died peacefully before it was forced to suffer this cruel transition. Instead, it lives on its current form, invoking images of guys in feathered fedoras strumming along to it around youth-group campfires, singing with the aggressive sincerity you’d expect to hear during a tearful rendition of James Blunt’s “You’re Beautiful.” Considering its miserable fate, I wouldn’t be surprised to see this song referenced in a future Supreme Court case, cited as a powerful case study for the widespread legalization of euthanasia.

Cali Swag District — "Teach Me How to Dougie"

Looking back on the emergence of hip-hop, as it rose from the concrete of the Bronx, materialized as an artistic outlet for the searing frustrations of a disenfranchised population, and painstakingly gained prominence amongst a population of gatekeepers who disparaged it endlessly, it’s interesting to imagine how many years of this process we might have skipped if a rapper had simply known to make a hip-hop derivative of the "Chicken Dance” in 1980.

The only thing white people like more than a choreographed participation dance is pretending to be “urban,” and “Teach Me How to Dougie” offers them the perfect outlet to fulfill both of these objectives. At the risk of sounding like a joyless monster, “Teach Me How to Dougie” has simply replaced the "Chicken Dance” or the "Macarena” as the worst part of any wedding reception. A modest proposal to any wedding DJs who might be reading this: if you absolutely must play a participation dance song, please play “Crank Dat (Soulja Boy)” instead. It’s not significantly preferable to “Teach Me How to Dougie” by any means, but the dance could, at the very least, be construed as a micro-cardio workout.

JAY-Z — "Empire State of Mind" ft. Alicia Keys

During a recent trip to a tropical resort, my arrival was greeted by a DJ whose primary job it was to stand in the guest services lobby and welcome exhausted travelers to their new destination by playing exorbitantly loud music. Given that this was literally his only job directive, I found it odd that he chose to include the song “Empire State of Mind” on his playlist. From my perspective, there were very few ways for him to fail at his job, but playing a song where the most prominent lyrics are “Now you’re in New York”—a destination we were decidedly not in—was one of those select few.

The fact that no one seemed to notice this misstep, either, speaks to the fact that this song’s omnipresence has drained it of all context and/or meaning. In the eyes of most people, this song is no longer a touching love letter to the city of New York, it’s simply a vehicle for a slightly grating Alicia Keys chorus that makes the hook to Whitney Houston’s “I Will Always Love You” seem almost subtle and understated.

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Eminem — "Not Afraid"

For as evident as it is that race has played a factor in fostering the sense of exceptionalism that has followed Eminem around for much of his career, the critics who would ordinarily be preoccupied with this fact tend to dwell less on it because it’s also undeniable that he’s an incredibly gifted rapper. Up until the release of “Not Afraid,” I fell into this camp as well. Scanning the song for redeeming qualities, I was unable to find anything but an irritating chorus that clawed at my skin and cringeworthy lyrics like “So fuck the world, feed it beans / It's gassed up, if it thinks it's stoppin' me.

Watching this song soar to No. 1 on the Billboard charts was the first time I remember thinking that Eminem was coasting off of his white privilege alone. To be clear, I know this is a controversial theory, but this song is so bad that I’m not leaving room for any other possible explanation to make sense. I know art is subjective, and I’m open-minded enough to accept that a black horizontal line on a white canvas could very well be a masterpiece, but I’m not open-minded enough to accept that someone might like this song based on its merits alone. This song is so bad that it made me reassess the entire critical framework by which I judge art.

Occasionally, I’ll see this song pop up in a movie trailer or a YouTube video, seemingly selected as a backdrop because of the motivational quality of its lyrics. From where I stand, this song is far more discouraging than it is motivational. I’m only half-joking when I say this song is so bad that it literally reminds me of the oppressive effects of white supremacy.

House of Pain — "Jump Around" 

I never got the chance to go to a ‘90s frat party—mostly because I was nine when the decade ended—but if I’ve learned anything from movies, these parties consisted of nothing other than barbaric hazing rituals, a palpable undercurrent of toxic masculinity, and the song “Jump Around” by House of Pain. Though I’d be hard-pressed to name all the movies in which I’ve noticed this specific cocktail, the song’s Wikipedia page provides a handy refresher course, listing 14 different movies in which it’s appeared, in addition to three different TV shows, and a commercial.

Over the years, this song has become a shortcut for lazy music supervisors to utilize ad nauseam whenever a script calls for a “vaguely upbeat, threatening-but-not-threatening hip-hop song.” Given the song’s repeated use in this context, I’ve begun to look at it as indistinguishable from all the royalty-free songs you often hear placed in media simply because they’re cost-effective. At this point, “Jump Around” is no different in my eyes from “Yankee Doodle” or “Old MacDonald Had a Farm.”

Macklemore & Ryan Lewis — "Thrift Shop"

After considering all the data points available to me, weighing the many implausible explanations, and examining every alternate timeline imaginable, I’m finally ready to venture my theory as to why, we as a society, allowed Macklemore to become a thing in 2012. This may sound farfetched, but hear me out: I think Macklemore is an evil genius who hacked into all of our personal computers and used compromising information to blackmail each and every one of us individually into liking him. I sense that you’re skeptical, but it’s definitely more rational than all of us collectively listening to a song where Macklemore refers to himself in the third person as a “cold-ass honky,” and then unanimously concluding, “Cool, let’s see where this goes!”

Jokes aside, I’ve come around on the idea that Macklemore is a well-intentioned guy who often gets a bad rap for a lot of things that are out of his control. “Thrift Shop,” however, is not one of those things. If it came out today, it would likely be lambasted as a poor Lil Dicky impression, but even in 2012, it wasn’t exactly groundbreaking. By sending up rap’s obsession with materialism, Macklemore wasn’t so much shifting the paradigm as he was ignoring the cultural context in which this obsession took root. It’s like he made a song about eating healthy called “Whole Foods,” trying to satirize a group of people who had just been granted access to fast food after an entire lifetime of being told this access was unattainable. I don’t hear much of this song these days, but its star burned so brightly while it was at its peak that I’d consider it a divine blessing from Lord Krishna himself if I never had to hear it again.

Kanye West — "Gold Digger" ft. Jamie Foxx

There’s something very surreal about shouting the lyrics “We want prenup, we want prenup!” in the middle of a wedding reception when you know for a fact that the couple has yet to discuss the logistics of dividing their assets in the event of a split. If I was the type to be superstitious, I’d be inclined to believe this was some sort of bad omen.

Yet, for whatever reason, this song continues to be played in these settings, likely because it’s the biggest hit of Kanye’s career. Reaching No. 1 on the Billboard Hot 100 for 10 consecutive weeks in 2005, it’s strange to think of “Gold Digger” as such a milestone for Kanye, primarily because it spends its entire runtime joking about a very specific problem that is relatable to almost no one. There is no scourge of gold diggers surreptitiously preying on the average person for their modest but comfortable $60,000/year salary. No one is poking holes in condoms for the possibility of one day winning a used Honda Accord in a divorce settlement. With this in mind, dancing to “Gold Digger” is not unlike dancing to a song about how much it costs some billionaire to fuel their private jet. Kanye has a very extensive catalog, let’s move on to literally any other of his songs that are more relatable.

The Notorious B.I.G. — "Hypnotize"

Undue nostalgia has a way of tarnishing everything we once loved. It’s difficult to count the number of great songs that have been ruined by uncreative DJs who play the same throwback playlist each night, nonetheless causing boring people to throw their hands up in the air and lose their minds at their own ability to remember a thing. 

The shining example of this phenomenon is The Notorious B.I.G.’s “Hypnotize”—a permanent fixture of these DJ sets, and one that almost always elicits such a nostalgic response. It’s also the example that never fails to baffle me. I’ve never quite understood how a song that has never really left the cultural zeitgeist can cause so many people to act so convincingly like they’d managed to forget about it. It’s like turning your head for a moment and then claiming you forgot where you parked your car. Considering how frequently most people still hear this song, it seems silly that we let it bathe us in nostalgia the way we do.

The great comedian Tig Notaro has a relevant joke about the contemplative half-exhale, half-moan noise people sometimes emit after a prolonged fit of laughter. Much like I do in regards to "Hypnotize," she ponders why people feel the need to reminisce on something that happened literally seconds earlier. Every time I see a crowd of people go crazy to “Hypnotize,” I think of this bit and wish this song would go away for just long enough to make the act of reminiscing on it see less trivial.

Drake — "In My Feelings"

I mean, do I really need to explain this one?



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