One of the many unique characteristics that sets rap apart from other genres is how effective it can be at functionally communicating a message. With less melody to distract audiences from the content of the lyrics, attentive listeners are often able to digest the message of a song on their first listen, thus allowing rappers to pack their songs with incredibly specific details. For the most part, this has led to great things—like the dozens of exceedingly intricate Nas verses that litter his catalogue—but, on the other hand, it has also led to many awful things, like the existence of rapped airline safety videos, which cause me to momentarily reconsider the merits of traveling by boat.
Rap’s unique communicative efficiency is something that audiences picked up on fairly early in the history of the genre. Evidently, it didn't take long for people to realize that rap could be used as an all-purpose novelty to jazz up any and all otherwise boring verbal monologues. Delivering a tedious presentation about ergonomics? Why not write a rap about carpal tunnel syndrome? Writing a commercial for a new accounting software? Ask yourself: how would Snoop Dogg do it? Trying to turn a 10th-grade history lesson into a hit theater production? What rhymes with Alexander Hamilt—you get the idea.
As the phenomenon of using rap as a functional method of communication ballooned out of control, the eventual rise of “comedy rap” seemed like an inevitability. Jokes, when deconstructed, are essentially just words, and thus cosmically destined to be mixed and matched with rap in a variety of ill-conceived ways. Yet, for something that should have been a fairly natural fit, examples of comedy rap over the years have been largely hit or miss. There are, of course, funny rappers, like Vince Staples, and isolated moments where rap is funny, like Chance The Rapper’s verse on Action Bronson’s song “Baby Blue,” but rap songs that are made for the express purpose of being funny are typically far less common, and generally far less successful.
It doesn’t help matters that, for years, examples of novelty rap—like those mentioned above—were mistakenly branded as “comedy” by people with an apparently relaxed stance towards the generally accepted notion that comedy must include jokes. To be clear, the only joke within novelty rap songs is rap itself. Novelty raps are conceived in boardrooms by out-of-touch creative executives who say things like “wouldn’t it be funny if we did a rap?” There is no additional layer of humor to dissect. Novelty rap songs are funny to the same type of people who laugh uncontrollably whenever they use a silly straw.
Further compounding this problem is the fact that comedy rap often gets lumped in with content that essentially boils down to, “look, it’s a white person rapping, which is an act that is stereotypically associated with black people!” The fact that anyone in 2017 thinks this is subversive enough to be funny is baffling to me, but it would appear that this type of humor stems from a long tradition of problematic comedy that has its roots in the minstrel shows of the 1800s. In these productions, white performers would wear blackface makeup and play shows for delighted white audiences who thought it was hilarious to see black people depicted as unintelligent, brutish caricatures. If you’ve ever seen the 2003 movie Malibu’s Most Wanted, you’ll realize that we haven’t evolved as far away from this as one might hope.
Intuitively, people who are in the business of making comedy rap probably aren’t thrilled that their artistic ambitions are weighed down by images of tacky insurance commercials and/or rapping grannies in blackface, and yet it is precisely these perceptions that they have to fight against every time they release a new song. They have to demonstrate that they have genuine respect for the craft of hip-hop by making music that sounds authentic, and they have to establish that their jokes are funny enough to stand on their own, lest they be accused of using rap as a cheap gimmick to elevate their mediocre material. With so many ways for comedy rap to possibly go wrong, it’s interesting to pinpoint the sporadic times when it unequivocally goes right, and dissect the many more times when it fails miserably.
The following songs are examples of comedy rap, some of which succeeded in striking the right balance and others that, of course, did not.
The Lonely Island – "I’m On A Boat" ft. T-Pain
As much as it may pain a generation of former 15-year-olds to read this, The Lonely Island’s viral comedy rap videos of yesteryear have not aged particularly well. Take, for example, their hit song “I’m On A Boat,” which features exactly one joke: The Lonely Island are on a boat. Watching this back for the first in about eight years, I audibly pondered to myself “what is this—I don’t get—why are they…” Maybe the joke has something to do with the juxtaposition of the inane content and the aggressive bravado of the delivery? I don’t know. This isn’t a New Yorker Column. I shouldn’t have to intellectualize it this hard.
In their defense, I doubt whether The Lonely Island made this song intending for it to have eight years of creative longevity. As time has gone by, Andy Samberg, Akiva Schaffer and Jorma Taccone have grown older, much like the rest of their audience, and have honed their sensibilities further. Their criminally underappreciated 2016 movie, Popstar: Never Stop Never Stopping, contained some genuinely hilarious examples of rap comedy, like the spot-on parody of Macklemore’s song, “Same Love,” entitled “Equal Rights.”
Rodney Dangerfield - "Rappin’ Rodney"
Prior to examining this song further, it’s important to acknowledge that it was released in 1983 (!), and was thus incredibly ahead of its time. To Rodney Dangerfield’s credit, this song was actually fairly authentic to its era, having been co-written by the same songwriters who worked on Kurtis Blow’s classic song “The Breaks.” Also to his credit, some of the one-liners in this song are decently clever jokes sourced directly from his standup (“I got stuck money, what did I do? / I bought some quicksand and the deal fell through").
And yet, somehow, it’s also the worst thing I’ve ever heard. It’s pretty safe to say that this is not one of those cases where the sum is greater than its parts. For all of its other redeeming qualities, this song falls victim to the same intangible quality that ultimately sinks most comedy rap: it’s extraordinarily, immeasurably corny.
Bo Burnham – "Little Teapot / Baa Baa Black Sheep"
Speaking as someone who is immediately skeptical whenever I hear a standup comedian reference rap music, the quality of this bit surprised me. In my opinion, this routine checks all the right boxes for what comedy rap can be at its most thoughtful. It helps immensely that Bo has the opportunity to provide a measured preamble before launching into his rap parody. Before beginning the song, he expresses a genuine reverence for the genre, disclaims that he’s aware that he’s not the genre’s intended audience, and then proceeds to explain his very specific criticism of modern rap music. The actual song—which involves rapping “I’m a little teapot” over a trap beat—could very easily have been reductive and demeaning if the execution of it wasn’t so pitch-perfect. By the time the chorus hits, it’s not hard to imagine that this song could be a real hit record played on mainstream radio and in clubs across the world. Adding to the success of the bit, Bo also has the wisdom to cut the song off after two short verses, acknowledging that to extend it any longer would be to milk it for limited comedic effect.
Lil Dicky - "White Dude"
It seems almost like a minor accomplishment to have made it over 1000 words into this piece without mentioning perhaps the most prominent figure in comedy rap today, Lil Dicky. Lil Dicky is a divisive figure, and much like former DJBooth scribe Lucas, I have some serious problems With Lil Dicky’s joke raps. Yet, in spite of myself, I have to admit that I’ve sporadically liked some of his output in the past. The Philadelphia native is an interesting microcosm of the comedy rap subgenre as a whole, as his songs are extremely hit or miss depending on the subjects he chooses to explore within them. And with that being said, “White Dude” was a huge airball.
“White Dude” begins with Lil Dicky levying the fairly uncontroversial premise that having white skin is generally advantageous within society. He then proceeds to support this premise by offering dozens of examples to prove why it’s beneficial to have white skin. Yet, it’s not like anyone heard this argument and was like “wait, I need examples.” The song is a huge miscalculation because it spends its entire four-minute runtime supporting a premise that necessitates absolutely no support whatsoever. It’s kind of like he made a rap song called “Some People Like Food,” and then spent four minutes defending this notion. It’s like, “yeah, Dicky, we’re all on board; you’re not arguing against anyone here.”
Mining delicate subject matter like this for comedy is a difficult task that requires subtlety and nuance. It’s something that Louis C.K. did artfully in a classic bit from his 2008 standup special, Chewed Up. Yet, where Louis C.K.’s bit succeeded because it read as a wizened comedian offering a humorous takedown of the absurdity of white privilege, Lil Dicky’s fails because it reads as someone bragging extensively about the benefits that this privilege affords him. As a general rule, it seems advisable for Lil Dicky to stray far away from bragging about how great it is to be white, particularly when he makes a handsome living working in a historically black art form.
Afroman – "Because I Got High"
This is an example of a comedy rap song that really shouldn’t work, and yet somehow manages to do so. Objectively speaking, it’s not very good. The joke is very one-note, there are too many verses, and outside of the context of a rap song, the material is incredibly thin. And yet, against all odds, Afroman’s ode to intoxicated neglect is universally adored by all those who remember it. It succeeds in much the same way a hypothetical standup comedian might if they were compensate for a lack of strong jokes by building a career off the back of an incredibly charming persona.
In this way, this song is kind of like the Kevin Hart of comedy rap songs.
Photo Credit: W Magazine