The question above, first asked by Frank Zappa, is serious. Zappa was one of the first to consider the question of whether humor could really coexist with music, or if it only succeeds in cheapening the quality of either. And for a long time, I've felt as if rock music in particular and humor have had a hard time negotiating with each other--so many musicians would take it the wrong way if their lyrics were to laughed at. In the last decade, though, I've noticed a series of developments that suggest that humor can have place in popular music, in a way that won't seem to cheapen those supposedly ineffable qualities that make music so powerful for so many.
First, let's start with what used to be the standard bearer of musical humor, a Zappa acolyte named Weird Al Yankovic. I happened to like Weird Al when I was in elementary school, but I grew out of him fast when I realized that most of the jokes were juvenile attempts at mimicking (as opposed to challenging or elaborating upon) whatever was successful in pop culture. If you'll recall, about half of his shtick was lifting the melody and vocal lines from popular tunes, and replacing the lyrics with more offbeat and specific topics (which most of the time happened to rhyme). So "I Love Rock 'n' Roll" becomes "I Love Rocky Road"--about the ice cream--and "Like A Virgin" becomes "Like A Surgeon." In my opinion, Weird Al ceases to be funny once you find that most of his work banks on a fairly consistent formula, usually involving rote pop culture phrases and statements. But for a while, in the 80s and 90s, he was about the best example of "humor" in music that I can think of, and he was hailed in at least some circles, like Spike Jones before him, as a brilliant music parodist.
The problem with Weird Al's stuff was that, most of the time, it wasn't funny. "Eat It" might seem like a funny riff on "Beat It" for ten seconds, but an entire 4-minute song constructed around making someone try to eat something isn't as funny once you have to figure out the rest of the words to fill time. Weird Al songs are generally highly specific and repetitive in this regard. For example, his take on Coolio's "Gangsta's Paradise" (itself a take on Stevie Wonder's "Pastime Paradise") is called "Amish Paradise," and it includes lines like "I've been milking and plowing so long/even Ezekiel thinks like my mind is gone." The joke, I guess, is that some Amish people are named Ezekiel, but that doesn't by itself make a particularly good joke. Some humor can be derived from Weird Al's appropriation of Coolio's flow, but the limits of the subject matter basically kill whatever humor is left.
Now that it is 2010, I look back on the last decade and see that there have been many significant advances in humor and quality music. Off the top of my head, I can think of the following bands that are both legitimately good and uniquely funny:
Electric Six: Though the band has yet to replicate the laughs of their album Danger! High Voltage, there was a time when Electric Six was writing ridiculously funny songs like "Gay Bar" and "Naked Pictures Of Your Mother." In this band's case, most of the humor was derived from the insane overdrive of their instrumental performances, coupled with subject matter that didn't necessarily seem to match up with all screams, cowbells, and guitar riffs. And of course, having the wailing Dick Valentine inexplicably reveal that it is a girl he wants to take to a gay bar. That, and he wants to start a nuclear war at a gay bar. Most of the humor of Electric Six comes from the sheer conviction of Dick Valentine saying the most absurd things, coupled with music that wouldn't sound too out of step with 70s classic rock. And with "Danger! High Voltage," the humor basically lies in Jack White trying to sound even more excited than Valentine. He kind of succeeds.
Eagles Of Death Metal: Similar to Electric Six, Eagles of Death Metal appropriate the irresponsible hedonism and sexism of a lot of blues-based rock 'n' roll, and amp it to such extremes that it is difficult to take seriously. Jesse "The Devil" Hughes is lucky enough to have a hilarious voice to begin with--it's like a high-pitched, crooning Elvis that contradicts his mustachioed, muscular image. Most of what I find funny about Eagles of Death Metal is in the way they deliberately misunderstand the point of music as a vehicle to get girls, blowing one of the key rules, which is that you shouldn't be blindingly obvious about who you look at as a potential conquest. Another funny, more musical trope of Eagles of Death Metal is that basically every song on their first album ends falsely, pauses for a few seconds, and then comes back into the chorus yet again. So, what seems odd and repetitive at first becomes more and more funny, and basically unique in the annals of popular music.
The Hives: In this case, it's perhaps not so much the content of the music as it is the persona of Howlin' Pelle Almqvist, another irrepressible showboat who is incapable of censoring himself or his love for his own music. The Hives were never as great as many of their contemporaries, but the band seemed to realize that, and they instead developed a public persona that poked fun at the wackiness of musicians who really think they are the greatest band in the world. Then there were their name, like the bassist Dr. Matt Destruction (who once said he could perform medical procedures "with his bass guitar") and Nicholaus Arson. Plus, they're Swedish and deliberately talk in broken English, which is always kind of funny anyway.
The Darkness: I will admit that not much of the Darkness' music is that great, but for sheer absurdity, they're really hard to beat. Indulging in every metal cliche, and possibly adding some new ones, they were like a bottomless repository of jokes, ranging from just general histrionics to extended metaphors about venereal diseases. This didn't last long, although their song "One Way Ticket To Hell...And Back!" always makes me laugh for good reasons.
These are four bands that I really think did positive things with humor in music over this last decade. I would also add McLusky as a band that I generally find to be pretty hilarious. I look at McLusky as more of a niche, though, as I don't know if lines like "I'm fearful of flying, and flying is fearful of me" or "we've got more songs than a song convention" are really funny to anyone but me.
On the flip side of this revolution in music is a similar revolution in comedians who are actually successful in producing good music, and I'm thinking primarily of two groups: Flight of the Conchords and The Lonely Island. Both of them manage to circumvent the Weird Al problem by producing songs that sound like particular artists or genres without actually copying specific melodies.
Flight of the Conchords' comedic worth was only exacerbated by the fact that they had a TV show where they were basically given carte blanche to construct a narrative around their songs. You can tell this is particularly needed in the second season of their HBO series, where there are notably more songs that are meant to advance the narrative, as opposed to the other way around. In any case, I think Flight of the Conchords' strength really comes from their genre parodies, particularly in how they subvert or undermine the subject matter that would normally accompany songs of certain genres. "The Humans Are Dead" purports to be a techno-futurist song set in a world where robots take over, but the narrator seems most hung up about whether or not all the humans are actually dead, or if they look dead. "The Hip-Hopopotamus Vs. The Rhymenoceros," meanwhile, takes a rather dead trope--white people and attempting to rap--and invests it with a removed sense of anxiety about being not being confident enough to freestyle. This always works better, I think, then when multiple songs in a row seem to all revolve around whatever the show's theme happens to be.
The Lonely Island, meanwhile, are primarily hip-hop heads who almost exclusively bank on the same white people/hip-hop trope. Again, there is incredible potential to not be funny, but the Lonely Island, at their best, marry such ridiculously high concepts to their raps that the humor comes from the methods by which they happen to stay on topic--how much can one really talk about being on a boat, or being a boss? Inverting hip-hop cliches has always been grounds for a lot of great comedy, and the Lonely Island does some of they appropriate certain cliches and act as if they are facts of existence. My favorite song of theirs is "Santana DVX," a song about how the group exclusively drinks sparkling wine made by Carlos Santana. The idea of a bunch of rappers sipping on sparkling wine is funny enough, but the humor is only exacerbated by their outsized love for Santana's music, proclaiming that "he teamed with Rob Thomas for a music revolution" and he "got laid all the time by 70s chicks." It also has the definitive Bay Area Hyphy rapper E-40 playing the role of Santana, without any attempt to sound like Santana in any way. It takes a music fan to enjoy the concept of Santana telling a group of admirers that "I see you bitches is enjoying my sparkling wine...be careful cause that shit will get you FUCKED UP." I laugh even writing these words.
Humor has made enormous strides (think of how Apatow has changed the game in a lot of ways), and I think we have an increasingly self-reflexive musical culture to thank for that. For the first time, people are seeing that subject matter isn't sufficiently funny in itself, except when wedded to a similar flaunting of musical convention--it's when people understand that they should have confidence in the strength of their melodies as well as their one-liners, that great comedic art can be made. I look forward to the next decade's unexpected marriages of humor and music.