Comedy can be hard to pull off in song. There's Weird Al, of course, and while he has given us plenty of songs worth celebrating, we're talking about a subtler type of humor. The kind of sarcasm prevalent in, say, a book from Tom Wolfe, who died this week at 88 and often used acerbic cynicism to illustrate uncomfortable – or ridiculous – truths about modern life, ala his take-down of New York nobility that remains Bonfire of the Vanities. Several songwriters are also well-versed in such a trade. This week brings us a new album from Stephen Malkmus, whose work with both Pavement and the Jicks has always featured a sarcastic edge. Here are five must-hear albums that find humor in cynicism.

Paul Simon, Stranger to Stranger
Paul Simon is highly regarded for his observational skills. The soft-voiced storyteller also has a reputation, especially earned during the latter part of his career, for being a connoisseur of global and exotic sounds. Simon's wry sense of humor can be overlooked, however, especially because his delivery is so casually straight. Droll cynicism defines Simon's recent Stranger to Stranger album. Opening track "The Werewolf," based upon the single-stringed Asian instrument called the Gopichand, is littered with a population polluted by capitalism – "the winners, the grinners with money-colored eye" who "eat all the nuggets, then they order extra fries." A song such as "Wristband" comes off as more light-footed and jazzy, spinning an amusing tale of a musician's run-in with an arrogant bouncer. The tune also illustrates the true gift of Simon's songwriting, in which a simple vignette about a VIP section becomes a stand-in for a grander message about the have's and have-not's.

Stephen Malkmus, Sparkle Hard
Pavement could be considered the slacker kings of alt-rock, with the band's obtuse pop-rock nuggets possessing a tossed-off quality. The group's biggest hit, 1994's "Cut Your Hair," took aim at the mid-90s rock scene and its rather instant commercialization – one in which then-contemporary artists, in Pavement's mind, emphasized fashion just as much as the hair-metal bands of the decade prior. Today, Pavement architect Stephen Malkmus continues to traffic in humorous cynicism. Now 51, Malkmus is less interested in jabbing at his peers and takes a longer view. With his long-standing band the Jicks, Malkmus on Sparkle Hard crafts a tightly wound and pointed look at life in modern-day America. "Bike Line" arrives as one of his more ferocious rockers, looking at our continuing racial divide and slamming pleasantries enjoyed by the well-off. "Refute" turns toward matters of the heart and becomes a sly, pro-LGTQ anthem in which a marriage comes to an unexpected end. Then there's the loose-swinging "Middle America," where Malkmus simply has enough of members of his own ilk messing up the universe. Men, he sings, "are scum," a term that seemingly applies regardless of haircut.

The Beatles, Revolver
The Fab Four? Sarcastic? On an album that contains the joyous and often perceived-to-be-silly "Yellow Submarine"? While the Beatles may not have been Monty Python when it came to scathing jokes, Revolver finds the act fully severing ties with the love-obsessed songs of yore and becoming cultural observants. They didn't always like what they saw. This, after all, is the album that opens with "Taxman," the George Harrison-penned tune instantly relatable to anyone to who receives a paycheck. "If you drive a car, I'll tax the street," Harrison sings, while a choppy guitar provides an exclamation point. Then, of course, there's the tense strings of "Eleanor Rigby," a composition that questions the point of it all – and on which a priest writes a sermon no one hears and Rigby serves as the star of an under-attended funeral. And don't overlook the scraggly "Doctor Robert," where a quack physician prescribes little more than illegal substances.

Randy Newman, Dark Matter
No list of this sort would be complete without mentioning Randy Newman, who could give a master class in writing from a sarcastic point of view. Save for his work for Disney and Pixar, listening to a Newman song requires an attentive ear. Did he really, for instance, just sing that when Russian president Vladimir Putin takes off his shirt, it makes Newman want to be a lady? Yes, yes he did just sing that, as the moment arrives on the simply titled "Putin" from last year's Dark Matter. At 74, Southern California's sonic jokester hasn't lost any of his bite. But Newman songs work even if you're not in on the joke. Just check the Los Angeles Dodgers, who continue to celebrate home wins to Newman's "I Love L.A.," a song on which West Coast denizens are too checked out to pay attention to the crumbling realities of the town around them. Dark Matter embraces Newman's left-of-center thinking more overtly than other albums, as its songs unfold as mini-symphonies to heighten the exaggerated theatricality involved.

Blur, Parklife
The mid-90s Britpop scene regularly utilized sarcasm, and not just in the bickering between Oasis and Blur that the British tabloids loved to chronicle. See Pulp's "Common People," which details the ways in which lower-class fashion became stylish, or pretty much the entirety of Blur's Parklife album. The title track, drenched in British slang, shows us scene after scene of the sort of gratuitous excess one can find on display at any city park. With vocals by U.K. actor Phil Daniels, it's more a mini-monologue than a song, broken up by Damon Albarn's soaring vocals in the chorus. The dance-friendly hit "Girls & Boys" remains largely open to interpretation. While it can be read as a liberating song dedicated to sexual freedom and gender fluidity, Albarn sneaks in references to STDs and paranoia, bringing a dose of reality to the club life the song appears to celebrate. The group also sends up the love song, with the grandly orchestrated "To the End" doing away with romance to document a relationship getting drowned in drink.

Photo credit: Giovanni Duca