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Kanye West, singing or rapping.
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I ain’t even gon’ leave without sayin’ somethin’ on this track
You ain’t gonna use me to just be singin’ hooks


  —Missy Elliott, “Ladies Night (Not Tonight Remix)”


Check the scenario. You’ve scored tickets to see your favorite rapper in concert. You can’t wait to enjoy an energetic set of your favorite beats and rhymes. Finally, the rapper takes the stage, grabs the microphone, and proceeds to test out a new tune in which the rapper…sings?


While your favorite rapper swoons and croons, how do you react? Are you baffled, shocked at the rapper’s audacity? Or do you say, “Hey, that’s not so bad”, and get your groove on to the emcee’s new jam? The answer is probably, “Well, it depends”, because there’s no way to know how you’ll react to a rapper-turned-vocalist until you hear the vocals. As we’ll see, it also depends on the context of the vocals and the intent of the rapper.


As you might guess, this discussion about rappers breaking out into song is inspired by Kanye West’s performance of his single “Love Lockdown” at the 2008 MTV Video Music Awards. “Love Lockdown” adds Kanye West the Singer to his well-established identity as a rapper and producer. He got suited up, strolled out, and went for the gusto, albeit with a little help from Auto-Tune. Now, my concern isn’t whether his singing voice is “good” or “bad”, or even if West should be singing or not. Rather, I’ve been interested in how performances like this fit within the whole of hip-hop and, perhaps more importantly, what the effects of such a performance might be. Looking at it from this perspective, West’s foray into singing isn’t all that unexpected. In fact, we probably should have seen it coming.


Historically speaking, rappers have had an awkward relationship with singers and the act of singing itself. I’ll never forget the quote from Will Smith, “the Fresh Prince”, that introduced Rap on Rap (1995), a collection of essays about rap music: “So long as there’s different types of music, rap will always be around. Besides, there will always be people that can’t sing.” Still, the relationship, while uneasy, has had a transforming effect on rappers and singers alike.


By nature, rap is a composite of a great many rhetorical, emotional, and communal elements. But we are most familiar with the images and sounds of rappers who brag and boast, and exude aggression. It is the stereotype of the genre, codified in the descriptive vernacular, like when an emcee “strikes the mic”, “eats a beat”, or “spits a verse”. James Brown used to say, “Hit me!” Rob Base & DJ E-Z Rock’s ‘80s-era super-jam “It Takes Two” signaled Rob Base’s opening verse with “Hit it!” Against this background, singing, stereotyped as silky and smooth, would seem an unlikely companion for rap, especially when the singing pertains to love, broken hearts, and relationships.


This is not to say that rap, as a genre, is incapable of supporting themes of love and heartbreak. If that were the case, we wouldn’t have had LL Cool J’s emotional outpour in “I Need Love” (1987) or Heavy D’s “Somebody for Me” (1989). In 2008, Murs and 9th Wonder’s free-for-download album, Sweet Lord, contained “Marry Me”, with Murs going all out to woo and romance his lady. What the above-mentioned stereotypes do, though, is suggest a rationale for the general audience’s apprehension at meshing rapping and singing or, in its most extreme form, a rapper who attempts to sing.


Rappers themselves have expressed this uneasiness, sometimes to the point of outright hostility. In “Turn Off the Radio” (1990), the ancestor to Dead Prez’s 2002 anti-radio joint of the same name, Ice Cube railed against the genre prejudices of radio deejays in refusing to offer hip-hop to the listeners. There’s a bit of ambivalence in his message, which makes the song all the more potent, because he advocates ignoring radio play completely (“‘Cause I simply said f*ck Top 40 / And Top 30, Top 20, and Top Ten…”) at the same time that he’s advocating inclusion (”...until you put more hip-hop in”). The speaker in Ice Cube’s song has enough awareness of radio programming to know how to diss it, and is clearly outraged at hip-hop’s exclusion from it.


Ice Cube blamed radio’s poor quality on its reliance on the “R&B love triangle”. Cube rhymes, “When you’re out there kickin’ it with the brothers / You don’t care about lovers.” What you care about, he says, is a rapper “goin’ buck wild / Throwin’ and flowin’ and showin’ new styles”. Here, Ice Cube hints at the reason for the awkwardness: how can you chill with your friends while listening to music you would normally associate with a romantic evening? It’s a contextual problem. What music does a hip-hop fan recommend for having a party or getting revved up for a competition? As much as I love his music, the answer is probably not Luther Vandross.


Chuck D and Public Enemy were similarly miffed at hip-hop’s lack of radio presence, notably in “Rebel Without a Pause”. “Radio!” booms Chuck D. “Suckers never play me.” Elsewhere on the legendary It Takes a Nation of Millions to Hold Us Back (1988), “Caught, Can I Get a Witness” finds Chuck and company defending themselves against the specter of lawsuits over their sampling techniques. In the midst of this, Chuck critiques the vocalists:


You singers are spineless
As you sing your senseless songs to the mindless.
Your general subject “love” is minimal
It’s sex for profit.


It’s true that Ice Cube and Chuck D were reacting to a climate that’s much different than the one we have today. Hip-hop didn’t have nearly as much mainstream presence in, say, 1989 as it does now. R&B was a staple, and critics, including R&B singers, weren’t shy about dismissing hip-hop as a fad or nothing more than noise and loud talking. Under these conditions, I can see why, lyrically, rappers would look to knock R&B off of its pedestal and priority in radio programming.


Public Enemy’s sampling argument that “y’all can’t copyright no beats, man” probably wasn’t the best legal defense (kind of terrible, actually), but it highlights the sampling issue as another source of awkwardness between rappers and singers. After all, rap samples music by lots of singers. Big Daddy Kane’s “Young, Gifted & Black” (1989) offered a clear response. Kane said these singers would “still be home with arthritis” if rappers hadn’t revived their favorite grooves by sampling them. Relative to the tension between rapping and singing, sampling introduces the plot wrinkle of dismissing R&B singers as soft and “spineless” while sampling R&B for hardcore rap tunes. Inconsistent? Maybe. And although there’s a case to be made that sampling can, depending on the use, convert subjectively “soft” material into “hardcore” subject matter, hardcore rap’s rejection of “lovers” confirms the dichotomy of singing as a “soft” art and rap as a pursuit reserved for the “tough”, the “bad”, and the manly. “Reality—that’s what they’re runnin’ from,” Ice Cube said in “Turn Off the Radio”.


In the early ‘90s, former N.W.A. member MC Ren cosigned the anti-radio and anti-singer sentiments and he synthesized them into an informal code of conduct for rap artists. Where Cube dismissed radio’s myopic programming, and Chuck D had “declared war on Black radio”, MC Ren was codifying the “Do"s and “Don’t"s for the “serious” emcee in his song “Kizz My Black Azz”. “I’m tired of rappers with live instruments on the stage,” he complained. “Save that sh*t for parades.” He went on to claim that “the pioneers didn’t draw bands in the blueprints / ‘Cause it wouldn’t make sense”. In his opinion, anyone performing with live instruments and a band should retire for “lookin’ like Earth, Wind & Fire”. So much for listening to the Roots, right? And what did MC Ren think about singing? He rhymed, “No more singing on the breaks, please / The sh*t is spreadin’ fast like disease.”


That doesn’t mean it didn’t happen, though. On the contrary, singers both known and lesser known appeared “on the breaks” in rap songs, belting out hooks. If you count Run DMC’s “Walk This Way” and Whodini’s “Friends”, as I do, it’s been going on at least since the mid-‘80s. Big Daddy Kane’s It’s a Big Daddy Thing (1989) is illustrative, containing the track “To Be Your Man”, an R&B-tinged slow jam with that heavy metallic Jimmy Jam & Terry Lewis-like drum programming. Backed by engaging soul riffs, Kane set out to romance his lady, the unspecified “you” of the song. It was kind of smooth too, in that old school “Hey, baby, what’s your sign” sort of way that only supremely cool cats like Billy Dee Williams could actually pull off. Kane was talking, not even really rapping, but its significance is the placement of the track on an album mixed with straight lyrical numbers, uplifting tracks (“Lean on Me”), radio hits (“Smooth Operator”, “I Get the Job Done”), bragging raps (“Mortal Kombat”, “Pimpin’ Ain’t Easy”), and the signature deejay track (“The House That Cee Built”) that often graced rap albums of the period.


“To Be Your Man” exemplifies the formula for rappers looking to be taken seriously in songs with singing elements. It’s a simple formula, really: hire a singer with a decent voice. The examples are abundant: Method Man and Mary J. Blige’s ” All I Need”, Tupac’s “How Do You Want It” (featuring Jodeci), Talib Kweli’s “Soon the New Day” (featuring Norah Jones), or Erick Sermon’s “Music” (with vocals sampled from the late, great Marvin Gaye). Any rap song that includes Nate Dogg is also likely to qualify.


Another significant point from It’s a Big Daddy Thing is that Kane and his crew did try singing the hook on the track “On the Move”. The operative word there is “try”. The singing isn’t stellar, or even all that serious for that matter. It’s a group of guys hanging out. For the most part, the hip-hop audience has been able to tolerate rappers who sing in a lighthearted way, whether for comedy or for hangin’ out with the boys. Consider a song like Biz Markie’s “Just a Friend” (1990), with Biz relaying a relationship sob story about a girl who denies having a boyfriend (“You say he’s just a friend!”) and then singing a gut-wrenching, tortured, and almost unbearable chorus between verses. This touch of humor helped Biz, already known for being funny, skate by with a “soft” love song and less-than-stellar, or nonexistent, singing chops. It’s a technique frequently put to good use. Erick Sermon’s sense of humor probably helped him get away with some rough vocals here and there.


The rapper-singer tension has also operated in the reverse, when rappers add a verse to an R&B or pop song. Rap cameos and rapper-singer collaborations have given us great results, in addition to pairings we never expected. Redman’s appearance on a Jodeci record (“You Got It”) worked nicely. Redman’s appearance, along with Tweet, on a Me’shell Ndegeocello track (the Rockwilder & Missy Elliott remix of “Pocketbook”) was weird. It didn’t complement the tone and texture of the album, Ndegeocello’s Cookie: The Anthropological Mixtape (2002), and therefore came off like an attempt to help a hard-to-pigeonhole musician like Ndegeocello appeal to a wider, presumably hipper, audience.


Hip-hoppers tend to view that type of collaboration as suspect. Parrish Smith (a.k.a. “PMD”) of EPMD summed it up nicely in “Crossover”:


The rap era’s outta control, brothas sellin’ their soul
To go gold, going, going, gone, another rapper sold
(To who) To pop and R&B, not the MD
I’m strictly hip-hop, I’ll stick to Kid Capri


Nevertheless, as rap grew in popularity and became increasingly infused in, and connected with, the mainstream, a rap cameo could be the difference between a chart topper and a dud. Don’t take my word for it. Ask Lil Wayne. He, thriving on the special guest honors of stars such as Redman and Method Man and Busta Rhymes, managed to sidestep the perception that getting paid for a verse on an R&B joint could be a form of “selling out” or evidence of some A&R team’s undue influence and culture-exploiting trickery. Rather, Lil Wayne, Redman, Method Man, and Busta Rhymes, among others, have been applauded as hard workers for cranking out so many verses for so many different types of artists.


It’s one thing for a rapper to provide a cameo in an R&B song or for a singer to lace a rap song with a soulful hook. Sometimes, rappers can get away with singing their own hooks, even if they’ve got, to quote the American Idol judges, more than a few “pitch problems”. But it’s a different matter altogether when rappers start singing whole songs. When that happens, the audience might accept comedic posturing, under the right circumstances, but the demands are heightened if the singing rapper wants to be taken seriously.


Mary J. Blige’s debut, What’s the 411? (1992), helped to legitimize the rapping-singing hybrid, as the soul singer worked her magic over backdrops rap fans instantly recognized as “hip-hop beats”. For instance, Audio Two’s classic “Top Billin’” (1988) was the backbone for Blige’s smash single “Real Love”. Executive produced by Sean Combs, then known as “Puffy” or “Puff Daddy”, What’s the 411? also lent credibility to the idea of a rapper trying to sing and a singer trying to rap. And it happened in the title track, of all places, where Blige joins Grand Puba, mostly known for his contributions to Brand Nubian’s debut One for All (1990). Blige kicked a few rhymes, and then Grand Puba returned the favor by singing a few bars. None of it was mind blowing, or groundbreaking, as Blige, unsurprisingly, isn’t the best emcee nor did she get the best lyrics (“You gotta do a lot more and that’s just how it be / I’m Mary Blige and you just ain’t runnin’ up in me”) and Grand Puba simply can’t sing a lick. But, appearing on an album that was otherwise cohesive and well executed, the experiment worked.


Where What’s the 411? built upon the hip and hop of Teddy Riley’s New Jack Swing, Lauryn Hill’s The Miseducation of Lauryn Hill (1998) brought authenticity and relevancy to the fusion of rapping and singing. Hill handled both with ease, as she and her crew, the Fugees, had previously scored a hit with their remake of Roberta Flack’s “Killing Me Softly”. Although I still insist that Miseducation isn’t as awesome as everybody says it is—not quite enough rap, too many meandering tunes, pointless background vocals, irritating untracked skits—the album’s importance in terms of impact and context is undeniable. Hill offered another avenue for rappers who choose to sing, this time with a caveat: feel free to sing your hooks and your songs of love and heartbreak, but it helps if your voice sounds good. To some extent, Queen Latifah is arguably a trailblazer of this paradigm, except Hill’s voice is stronger and Ms. Hill, quite frankly, was better at it.


Now, given this history of What Happens When Rapping Meets Singing, it’s easier to see the patterns. There are numerous examples of the two methodologies we’ve discussed. There’s the singing-for-fun variety, on the one hand, and the singing-for-real variety, on the other.


The fun, comedic releases are easy to spot. These days, they usually feature T-Pain and his digitally processed vocals. I didn’t believe it at first, but I’m thoroughly convinced now that while the “revolution” won’t be televised, it will almost certainly be Auto-Tuned. Long before this, though, the streetwise N.W.A. sang two songs (“Automobile” and “I’d Rather F*ck You”) on their second album, N*ggaz4Life (1991), basically taking existing songs, like “I’d Rather Be With You” by Bootsy Collins, and dirtying up the lyrics for comedic effect. I admit I totally rejected Eazy-E’s singing when this album was released, but the album itself hit the top of the charts—a groundbreaking moment for “gangsta rap”—so I’m left to assume that somebody out there liked this sort of thing.


Likewise, Notorious B.I.G.‘s “Playa Hater”, from his double disc Life After Death (1997), showcases the rapper’s mellow singing delivery, which reminds me a little of Rick James. I’ve always been curious as to whether or not Notorious B.I.G. intended this song to be taken seriously. Personally, it cracks me up listening to him sing about a robbery in an easy listening style.


From Snoop Dogg\'s \

From Snoop Dogg’s “Sensual Seduction” video


In the new millennium, Snoop Dogg’s quirky singing, in “Sensual Seduction” (for the radio) and “Sexual Eruption” (the album version), illustrates how the fun mood and party atmosphere surrounding a rapper’s vocals can help the song succeed. “Sensual Seduction” is a slick come-on that extended Snoop’s preexisting dalliances with singing. Where he had previously tried to hold a note or two in the middle of his rap verses and choruses, “Sensual Seduction” found him in full singing effect, for better or worse. That Snoop delegated to others the majority of the songwriting duties of Ego Trippin’ (2008), the album containing “Sensual Seduction”, further supports the comparison between Snoop and the typical view of a vocalist singing material written by others.


To take matters further, and maybe complicate them a little too, Snoop also unleashed his passion for country music on “My Medicine”. Dedicated to Johnny Cash, “My Medicine” featured Snoop’s best attempt to make things less quiet on the western front. I could almost see tall and lanky Snoop Dogg camped out under a crisp and clear starry night, singing in front of a small crackling fire and taking steady sips from a never-ending flask. Snoop’s slice of country might also bring to mind the collaboration between Nelly and Tim McGraw. At the same time, the part of me that digs country music is a little bothered by “My Medicine”, and my love for Prince and Prince-related jams meant I was destined to be livid at Snoop’s remake of “Cool” by the Time. Snoop kind of took some of the funk out of “Cool” for me.


On the flipside, audiences are increasingly receptive to the rapping-singing fusion when (1) the singer who tries to rap is decent at rapping or (2) the rapper who tries to sing can hold a note. Singers who rap, or at least offer spoken word, include Floetry, Jill Scott, and Estelle. Jill Scott’s 2007 release, The Real Thing: Words & Sounds, Vol. 3, saw the brilliant vocalist upping the amorous content of her lyrics, and a couple of her “raps” could be described as kind of raw, at least in comparison to her previous output. But, you know, everything’s relative. It would be tame if we were talking about Luther Campbell and 2 Live Crew or Devin the Dude. Devin has, as a matter of fact, built his resume on singing and rapping in this very manner. As another example, U.K. singer Estelle has garnered comparisons to Hill, especially with her album Shine (2008), which includes input from none other than former Hill associate Wyclef Jean.


Rappers who sing are having a great time and fans seem to be responding. Here, we’re talking about acts like Cee-Lo Green and his Gnarls Barkley project, Andre 3000, Chamillionaire, Pharoahe Monch, Mos Def, Pharrell, Missy Elliott, and Phonte of Little Brother. Two interesting highlights from this bunch, both from 2008, are Pharrell’s singing on the N.E.R.D. album, Seeing Sounds, and Phonte’s collaboration with producer Zo! called Zo! and Tigallo love the 80s. In the latter title, by the way, “Tigallo” is Phonte’s nickname. I find Pharrell’s singing interesting because, really, it’s not that great, but I am nevertheless pleased by a few of them. “Happy” is my jam, actually, and I can’t even begin to explain why. This goes to show that there are exceptions to the general rule that you have to sound “good” to get away with a “serious” song. Or maybe the rule should be modified to say, “Go on and sing, but you can’t sound too bad.”


The collaboration between Zo! (he’s the producer) and Phonte (he’s the rapper-singer) intrigues me for its music and choice of material. Phonte has a solid singing voice, but they chose to cover some popular tunes from the ‘80s. They do stuff like A-ha’s “Take on Me” (remember the awesome animated video for that song?), Toto’s “Africa”, Joe Jackson’s “Stepping Out”, and “Written All Over Your Face” by the Rude Boys. This eight-song project offers a lot of fun along with the palatable vocals. Covers aren’t easy to handle, in my opinion, because they are invariably compared to the original, but I think the novelty here makes the project worth a listen. Besides, you can tell they actually tried to make it sound good. It’s not like they were pulling a “Weird Al” Yankovic and spoofing the ‘80s.


The effect of all this singing, whether it strikes the listener as “good” or “bad”, is hip-hop’s further democratization of music. That is to say that hip-hop can, in some respects, be viewed as a genre that’s open to almost anyone. We’ve got a problem right now getting the ladies in the spotlight, and the legacy of Vanilla Ice still sort of spoils things for white rappers, but that’s another matter. Theoretically, at least, if you can talk, you can rhyme, and if you can rhyme, you can match your rhymes with a beat in a compelling way. Theoretically, anyone can rap. It just seems more feasible that the “average person” could, with some effort and coaching, emulate Run DMC rather than Aretha Franklin. At least you’ve got a shot in rap, no matter how slim.


Speaking of Run DMC, they helped change the look of the entertainer, dressing it down with their casual stage attire and their famously unlaced Adidas. Rappers didn’t dress up like the Temptations. They dressed in everyday clothes. Much like Bruce Springsteen and John Cougar Mellencamp, Run DMC appealed to people’s real life experiences.


Where we once looked at our stars as untouchable and beyond the reach of the average fan, these days we’re often looking for stars we can identify with, people who appeal to us because they, or the messages in their art, remind us of ourselves. We still “look up to” talented folks, but we’re also looking to connect. In hip-hop, rappers have received notice for “humanizing” their personas and making their subject matter relatable to listeners. You might recall that the legacy of an album like N.W.A’s Straight Outta Compton (1988) was the fact that the hardcore lifestyle depicted in the album’s lyrics were unfamiliar to listeners. These days, we applaud the familiar, the universal, the global. I can’t help but think, then, that rappers who sing are, by trying something generally outside their comfort zones, following a path that is more inclusive. Maybe it taps into the listener’s feelings of, “Hey, I can do that”, which translates into, “Hey, this person isn’t much different from me.” And, in the long run, maybe rappers who take chances with their music can encourage us to take a few of our own.

Quentin Huff is an attorney, writer, visual artist, and professional tennis player who lives and works in Winston-Salem, North Carolina. In addition to serving as an adjunct professor at Wake Forest University School of Law, he enjoys practicing entertainment law. When he's not busy suing people or giving other people advice on how to sue people, he writes novels, short stories, poetry, screenplays, diary entries, and essays. Quentin's writing appears, or is forthcoming, in: Casa Poema, Pemmican Press, Switched-On Gutenberg, Defenestration, Poems Niederngasse, and The Ringing Ear, Cave Canem's anthology of contemporary African American poetry rooted in the South. His family owns and operates Huff Art Studio, an art gallery specializing in fine art, printing, and graphic design. Quentin loves Final Fantasy videogames, Barbara Kingsolver's The Poisonwood Bible, his mother Earnestine, PopMatters, and all things Prince.


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