Let's back into thisone with the sort of SAT analogy that can help us tidy our thoughts, like "painting is to frame as freak is to cage"—yessir, that'll do. That's the primary lesson of the chapter on sideshow freaks in Janet Davis's history The Circus Age: The all-important cage, she explains, transformed ape men and one-eyed monsters from pitiful curiosities into objects of subtle male envy. This was back in a Victorian time when the loss of America's wilderness stoked fears that the loss of America's manliness was next.

Roughly 100 circus seasons later, the American male wilderness lives on in the work of two modern-day freaks: Devendra Banhart (28, centaur progenitor, primary architect of what some describe/deride as "freak folk") and R. Kelly (42, sexual degenerate on-record if not in court, and a "dog when I'm walking through the mall"). On their new records—What Will We Be and Untitled, respectively—these two pansexuals flaunt personas as silly and erotically liberal as ever. But if they imagine themselves as virile objects of male envy, they're also objects of pity, trapped as they are by the cages in which freaks tend to roll through town. The thought holds especially true of R. Kelly, who, on Untitled, sounds more like a prisoner of his appetites than a creature of them.

Actually, the same might hold for Banhart, whose primary hang-up involves exiling himself into an aural dreamscape of sepia-toned, old-fangled sentimentality. Partly, that kink comes through in Banhart's voice, which resuscitates various 20th-century weirdos gone/not forgotten: He can coo haunting quivers alongside blackface's creepiest minstrels, croak a hernia-inducing Cat Stevens groan of dog-tired protest, and bellow with enough Halloween boom to reanimate Jim Morrison, but what he really brings to Weirdolandia is a willingness to dive lower on the regression/immaturity scale than even the Lizard King would crawl. We're talking psychedelic baby babble, hoots, inexplicable cackling, giggling gibberish, zany iambic pentameter, and general fun-loving Peter Pan–isms that counterbalance the aged sagacity of, say, Cat Stevens.

Often, however, Banhart's self-exile to the Age of Cute teeters between childlike and childish—his antics can be as glib as the aged sagacity they're designed to diffuse. Me, I like to hear some motion in my psychedelic folk, to hear the eccentrics involved navigate the perilous road between the all-purpose recalcitrance of adolescence and the more principled recalcitrance of acquired folk wisdom.

Luckily, that's what Banhart's up to here. On "Rats," he matches monkey hoots and giggly hiccups with fully fleshed rock riffs that signify as macho, manly, mature. For "Foolin'," he moans his silly ghost/blackface impression over a world-weary Upsetters-style skank that signifies as wise. On "Baby," a newborn somersaults into Banhart's world, presumably displacing Banhart himself: "Holy moly, you crack me up," the singer remarks to the babe whose arrival has awed, humbled, and humanized the Mountain God. What Will We Be is neither trim nor consistent, and its excess seems to flow from carelessness, not exuberance. But it's good growth for the freak involved—and for men, generally.

R. Kelly's new opus, on the other hand, hits all the sweet spots—with 808s and piano rolls mixed in a place still called the Chocolate Factory, the production is as efficiently romantic as you'd expect. And yet, in contrast to Banhart's messy maturation, Untitled feels like a petty, disappointing accomplishment. 2007's Double Up featured imaginatively self-aware dramas like "Same Girl" and "Real Talk"; this time, Kelly all but concedes his creative fatigue on "Like I Do": "There's only two things in this world that I'm the best at," he croons. "Number one is music/And baby girl, number two/Can't nobody rock your body like I do."

But about that: In 2009, both talents sound ever more like they stem from the same skill set. Yes, Untitled packs beaucoup horndog lyrics—"Kells gives sex seminars," ha, ha, ha, etc. But his sex talk is increasingly employed as a metaphor for the audience-artist relationship: Every amorous come-on is voiced at the rhetorical "you," his listener. The crafts of lovemaking and songmaking preoccupy Untitled, especially on the Europop number "I Love the DJ," in which Kelly's crush on a she-J doubles as celebration of r&b's current trajectory. Then there's "Number One," which is either a No. 1 record about having sex, or a No. 1 record about making sex that's as good as a No. 1 record. Draw your own sex-music-sex infinity loops.

Still, any attempt to thread larger themes from Untitled's sex seminars dies quick, considering that R. Kelly is presently invested in only one kind of sexual encounter: the conquering, pin-her-on-the-wall, victorious-tears-of-joy style prevalent in the innocent fantasies of idiotic boys. Check the hyperbole. In the course of Untitled, R. Kelly has you 1) sounding like you're screaming from a mountain peak; 2) banging the headboard; and c) grabbing your ears. On "Echo," he even makes you yodel—yodelayheehoo.

This is what is meant by the term "trappings of success." The more clubs, charts, and ladies R. Kelly conquers, the more his art becomes about the sad gilded cage than the freak locked in it. He pops a "$1,000 tab" on "Crazy Night," but sounds less thrilled than vindicated to be getting drunk off the per capita GDP of Pakistan. You can hear it in his voice, which sounds torn with raspy stress lines, and carries memories of the 2Pac '90s, when success = vengeance.

It's tragic to see a master of r&b finesse fall back onto a childish, domineering bent that comes off as boorish, entitled, and mean-spirited. Lest we doubt R. Kelly's reluctance to slide into the gentler, more bemused Hugh Hefner phase of bachelorhood, the album ends with "Pregnant," a thoroughly repugnant track that the NAACP will probably have to publicly disown. "Girl, I just wanna get you pregnant," Kelly declares. "Lay you down." Whether she's being laid down on the living-room rug or in society isn't clarified, or maybe it is: "I'm 'bout to handle my business," he concludes, "and put that girl in my kitchen."

Question: How can a record so intent on handling business and/or demonstrating mountain-peak, yodel-inducing levels of man prowess be so simultaneously juvenile? Maybe because America's dysfunctional marriage system, of which Kelly is a product, helps consumer culture glamorize an endless summer of adolescence—or, relatedly, because the pressure on men to remain forever virile sells Cialis and stirs inner demons on both sides of the sideshow fence. A man willing to go a little soft in his forties, though—now that would be the great American freak, monster, perv.

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