Some Of The Most Unlikely Rap And Pop Star Collaborations

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On Wednesday, Taylor Swift posted a photo of the tracklist to her hotly-anticipated album, Reputation, confirming the longstanding rumor that Atlanta trap rapper Future would be featured on the album. Not only is the lean-sipping rapper included on the second track, titled “End Game,” but he also appears alongside chart-topping ginger wunderkind, Ed Sheeran.

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The revelation made plenty of fans sit up and take note, but not all of the responses were positive. Mainly, it seems fans are incensed, disgusted, or outright befuddled at Future’s presence on the album, thanks to a perceived disparity between the two artists’ fan bases. However, the pair may secretly be perfectly suited to each other’s styles, with both having a propensity for addressing exes and drama in their lyrics and a shared — ahem — reputation for pettiness directed at their songs’ subjects. Behold Future’s “My Collection” video, widely believed to be a not-so-subtle shot at ex-wife Ciara. Or, take into account the ongoing feud between Swift and fellow pop star Katy Perry, with whom she’s carried on a four-year cold war over a dispute stemming from the double-booking of some tour backup dancers and at least one shared ex — guitarist John Mayer.

However their music styles may clash — or mesh, for what it’s worth — Future and Swift’s collaboration may come as a surprise to some. But, this isn’t the first time music industry manipulations tried to cross-pollinate fan bases between stars of opposing genres. In fact, rapper-pop singer collaborations have often times been one of the record business’ trusty tactics in trying to introduce new artists of either genre. The strength of the effect looks to stem from the juxtaposition of the stereotypically rugged, streetwise black rapper with the innocent, highly-curated blonde “pop princess” archetype — although it can be spun from the male perspective, too, as we’ll see in the list. There’s a lot of tangled racial politics at play in the practice, but that’s a whole different essay.

Intriguingly, the genres were kept as separate as possible throughout the ’90s, the era of the biggest explosion of growth for hip-hop, but by the early 2000s, the nascent genre had become undeniable and record execs began experimenting to try to find ways to export rap’s swagger to pop’s hermetically-controlled environment. Sometimes it works, and sometimes you get Rebecca Black’s “Friday,” which won’t be included in this list on principle. While this sort of collaboration has become more commonplace and even expected in the modern, ultra-saturated pop landscape, every once in a while, a rap-pop collaboration will still mashup such divergent styles that the result seems more haphazard than carefully calculated, even if the gambit is more of the latter than the former.

Below are six more times, from the earliest faux pas to the most recent headscratchers, rappers and pop stars created collaborations that made fans go: “Huh?”

Willa Ford X Royce Da 5’9 — “I Wanna Be Bad”

Truth be told, I’m a little astonished and saddened that so few people seem to remember this bizarre experiment from 2001, possibly one of the first in tying a more “hardcore” rap act to a polished pop song in order to lend it that coveted “edge.” It’s probably because the song (rightfully) bricked at just 250,000 records sold — in the era when pop singles were considered failures at anything less than platinum — and sounds exactly like it was born in a boardroom rather than a studio session or random meetup of like minds.

The pop parts are generic while the rap is uninspired and out-of-place, especially coming from a lyrical luminary like Royce. Ultimately, it’s probably best that everyone does forget this disaster of a song. I apologize for even bringing it up.

Christina Aquilera X Redman — “Dirrty”

This song is notable for improving on the formula of “I Wanna Be Bad” in every way, picking a distinctive bristly beat that matches the grimier aesthetic of the song’s Fight Club-cribbing music video. It’s generally considered to be one of the first successful fusions of manufactured pop and authentic, gritty hip-hop.

In retrospect, it’s a typically overproduced, chintzy, early-aughts slice of cheesecake with an inexplicable titling quirk, but it’s the comforting kind that delivers a healthy dose of genuine nostalgia and an infectious energy. While the song was a huge jam, and controversial at the time of its release, eventually Aguilera went back to penning ballads and unfortunately, Redman’s mainstream notoriety never reached the same levels. His more recent output has been lower profile, and the world’s pop stars have moved on to other, more current rappers to borrow cool points from.

Justin Bieber X Ludacris — “Baby”

As hard as it may be to believe now, there once was a time a burgeoning Canadian teen pop product needed the cosign of a raunchy-rapping, veteran party MC to crossover into mainstream consciousness. Now, Justin Bieber has become renowned for making urban-accented bangers while Ludacris is more known for dropping clunky, out-of-touch duds and flexing his acting muscles — and physical ones — in the Fast And Furious action movie franchise. “Baby” isn’t exactly a terrible song, but the idea of combining a baby-faced 13-year-old with a then 33-year-old lyricist best-known for such hits as “Move B*tch” and “What’s Your Fantasy?” was questionable then and seems practically inconceivable in today’s “woke” era.

Like many of the artists on this list, Bieber learned the value of the “code switch” while Luda’s more loyal fans were left wondering why he would agree to such an unhip association with a teen idol. While it was likely a great business decision at the time, contributing to the recognizability that led to his no-doubt lucrative multi-film role, his authenticity as rapper took a hit. That isn’t always a problem (at least, it isn’t now), back then it partly helped ding his sterling reputation and start his transformation into a past-his-prime, corny old guy.

Wale X Lady Gaga — “Chillin'”

You know how hip-hop often takes time out of practically every Wale profile or review to marvel at how the DC spitter revived his career on Maybach Music, capping a rare second chance in the record business? This is the song that killed his first chance. It’s a bit of an oddity on this list, in that this is Wale’s song, appearing on his Attention Deficit debut album. The shoehorning was so egregious, though, that it’s impossible to leave off the list. It also stands out because neither artist was 100% established yet, and thus neither was being used for the almighty co-sign. Instead, this was one of those situations where someone at the label thought one hand could wash the other, so to speak, and that a high tide for “Chillin'” would lift both Wale and Gaga’s boats.

Instead, “Chillin'” nearly torpedoed Wale’s career when his day-one, mixtape/blog fans interpreted the move as a complete 180-degree turn and a desperate grab for pop stardom. Gaga’s fans largely ignored the strained combination that relegated the singer’s powerful pipes to a singsong hook, reducing her usual belt to a chirpy refrain that masked the best part of her talents. Both artists wound up running as far as they could in opposite directions after this combo. Gaga tried nearly every genre but rap and ultimately stepped away from music for a while. Wale abandoned the homecooked go-go that had been a huge part of his early appeal in favor of boisterous, trappy strip-club anthems.

Katy Perry X Juicy J/Snoop Dogg/Migos — “Dark Horse”/”California Girls”/”Bon Appetit”

I couldn’t decide between the three examples listed, so I just called it a tie and included all three. They all fit for more-or-less the same reason: Katy Perry has always presented herself as a sort of a cartoon, and while each of the three rap acts involved has engaged in their own exaggeration and self-aggrandizement, they all hail from a mostly grounded, true-to-life sort of place. Juicy, Snoop, Offset, Takeoff, and Quavo all rap about relatively straightforward ambitions: Making money, chasing women, smoking copious amounts of weed — you know, the simple life.

In contrast, Katy Perry is all about the bombast; she’s always going for bigger, louder, and more. She wants the cotton candy, cupcakes, cookies, and candy, all piled on top of a triple-decker waffle with ice cream, chocolate sauce, syrup, and whipped cream. Not to mention, her subject matter, which never really got much racier than kissing another girl at a party, clashes mightily with Snoop’s one-time assertion that he has “women in the living room getting it on,” or Juicy J’s boast that “you say no to ratchet p*ssy, Juicy J can’t.” And unfortunately, it’s difficult to forget Migos’ adamant refusal to participate in her stage concept for a recent late-night appearance featuring members of a drag troupe. When it comes to Katy Perry, the reach for crossover appeal tends to ring even more hollow than it usually does, and often results in a product that sounds just as disposable as the sticky memo from which each poorly-conceived attempt probably spawned.

Taylor Swift X Kendrick Lamar — “Bad Blood”

It’s the circle of life; everything ends where it begins. Swift’s unexpected and honestly baffling inclusion of a song with Future sparked the idea behind this list, so it seems only right that her previous foray into reaching for rap street-cred adjacency makes the list as well.

Now, this is not a knock on “Bad Blood,” but on a list of rappers I’d have expected T. Swift to tap for such an endeavor, Compton’s own Kendrick Lamar ranks around 52nd, after Kanye West (for the shock value), Jay-Z (for the potential earnings involved), Drake (lol), and 49 blank spaces. They just don’t appear to have anything in common musically, personally, aesthetically, or even geographically. And yet, there was Cornrow Kenny sitting aside America’s Sweetheart in an invisible automobile, the only male presence in a video full of female assassins, ninjas, superheroes, and soldiers, sticking out like a sore thumb in a Dodgers cap. It’s an apt, albeit probably accidental, visual metaphor for the partnership itself.

However, it may be notable as the first video on the list (chronologically; “Bon Appetit” came out after “Bad Blood”) that didn’t curb the rapper’s trajectory by its mere existence. Kendrick’s follow-up album, DAMN., continued his stellar critical and commercial record, proving the value in his habit of jumping on questionable, less-than-hip artists’ songs, Coldplay and Maroon 5. Meanwhile, Reputation still has yet to be released, but the reception for Taylor’s latest singles hasn’t been as complimentary as her previous efforts. Now that hip-hop is the most popular genre on the charts, maybe the addition of a rapper or two to a tracklist is the shrewdest move a pop act can make — even if the combination doesn’t always make the most sense.