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As band names go, “Pinetop Seven” isn’t exactly the most accurate: It both under- and overestimates the group it’s attached to. On the one hand, nearly two dozen musicians have wandered in and out of the Chicago alt-country collective’s ranks since its founding about 10 years ago. On the other, Pinetop Seven is arguably a one-man band. Despite strong support from, let’s see, 11 other musicians—trumpeter/fluegelhornist Nate Walcott, for instance, or string players Melissa Bach, Andra Kulans, and Jody Livo—Darren Richard pretty much takes center stage on Pinetop’s fifth full-length, The Night’s Bloom.

It’s not simply because he wrote all the songs. Three instrumentals notwithstanding, he also sang all the songs, recorded all the songs, and mixed all the songs. Richard is also an instrumental polymath. Across the album’s 13 tracks, he plays everything from melodica, marimba, and sleigh bells to banjo, accordion, and guitar—acoustic and electric, nylon- and steel-string, slide and non-. My mental image of “June”’s recording session is particularly ridiculous: Richard scurrying around the group’s attic studio from guitar to vibes to piano to Casio to snare drum while the lone additional player, bassist John Peeler, thumps away. The man is a living advertisement for the wonders of multitracking.

That doesn’t mean The Night’s Bloom is especially lush, however. “Easy Company,” for example, sends Walcott’s trumpet snaking through a repetitive acoustic-guitar figure and some spooky vibes in a way that’s more noir than Nashville. “Fringe” piles piano over strings—and even breaks out those sleigh bells—to equally stark ends. Though there are plenty of potentially bright, brisk sounds thrown in there, the results don’t often come across that way.

One reason is that Richard & Co. typically forsake conventional—and, at times, discernible—verse/chorus/verse structures in favor of free-form mood-conjuring. That’s probably for the best, given that the heroes—or, more accurately, the protagonists—of Richard’s songs aren’t the kind of guys you’d want running around waving sharp hooks anyway. If rock ’n’ roll is happy songs about sad things, Pinetop’s music is sad songs about even sadder things—though Richard is ambiguous enough a lyricist that it can often be hard to tell what all the musical weeping is about. The jittery jazz of “June” sounds as if it could be backdrop to an act of either creative sex (“Won’t tell you what we did/Don’t know the name for it”) or violence (“I’ll take the blame if you want me to/They’ll never look at me again that way”). “Witness,” with its references to abuse and its closing-scene funeral, could easily describe a patricide. Or not.

Women have a limited array of roles, from nurturers (“A Fire Burns at the Foot of Our Bed,” “His Aging Miss Idaho”) to conquests (“Fringe,” “Easy Company”) to unattainable—and therefore doomed—objects (“A Page From the Desert”). “I’m lazy, I’m selfish, I’m all that’s bad in men,” our nonhero freely admits toward the end of “Fringe,” and the consolation he offers is even worse: “You’re smarter now, doesn’t that count for anything?” There’s more than a little creepiness along the way, too, as Richard’s character admires “their rose colored mouths, their paper white ankles/The goodness I see in their eyes.” The last, naturally, will fade as “a girl’s education begins.”

All of which makes the last vocal track, “Made a Whisper Out of Me,” something of a standout. Its grief, at least, is easy to sympathize with: “She would’ve been ten today,” Richard sings against a sort of half-speed waltz. “Half grownup with grownup things to say…/A looker like her mom—smart, delicate and strong/You both deserved more than me.” Another standout, “A Mouthful of Expensive Teeth” initially suggests such Richard-ready subjects as late-night brawls and crushed dreams. But when the singer strays from the milieu he’s sketched well on other tracks and into politics, his ellipticism works against him. “Raising a glass, to the friends that we’ll use/We’re bullies grown up with American views,” he offers. “It’s hardly good news/And it’s hardly news.” Given that the lines are followed by lyrics about metaphorical deafness and blindness, it’s hard to shake the notion that the blanks should be filled in by blue-staters only.

“Teeth” is the only real lyrical misstep on The Night’s Bloom. And musically it’s as good as most anything else on the album—or, for that matter, anything else in the band’s catalog. Indeed, right down to the instrumental opener and closer, The Night’s Bloom is pretty much just like its predecessors: an elusive not-quite-concept album that reveals itself slowly but surely. If that sounds like both an under- and an overestimate of the group it’s attached to, then Pinetop Seven has lived up to its name.

Edith Frost has had her share of help in the studio, too. Former Pinetop bassist Ryan Hembrey even lent a hand on 2001’s Wonder Wonder and the new It’s a Game. But Frost prefers to be known non-numerically: as…Edith Frost.

For her, that’s better than being known as Liz Phair. Frost’s sophomore LP, 1998’s Telescopic, made her a dead ringer for that particular shoulda-stayed-indie diva, not only because of the women’s eerily similar voices, but also because of the album’s lo-fi sound. With the guitar fuzz and drum flourishes now burned off of her songs, the style Frost has arrived at two albums later is both more conventional and more her own—not quite broken-hearted country, not quite smoky-lounge jazz.

Just as It’s a Game’s liner notes reveal the disc’s song titles simply by knocking them up a few point sizes within the lyrics, the best tracks on It’s a Game stamp their themes into your brain by attaching them to big ol’ hooks. We get ’em on the futility of romance (“A Mirage,” “Lucky Charm”), the futility of communication (“If It Weren’t for the Words”), or the futility of expecting a boyfriend to do the right thing (“My Lover Won’t Call”).

Not that the lyrics are devoid of subtlety: “Playmate” starts off with a lengthy “Iiiii” on each of the first three lines and ends with a triple imperative: “Come shine over me light/Come slide into the night/Come slowly into my room.” And “What’s the Use” goes, on subsequent choruses, almost imperceptibly from “What’s the use of trying?” to “What’s the use of trying again?”

The music is similarly simple ’n’ sturdy, with most of the instrumental adventuring confined to the breaks. “A Mirage” bolsters gently plucked guitar with gentle strings. “If It Weren’t for the Words” offers a harpsichordy something that gives way to a chiming organ. The title track features a soft opening with brushed drum and descending piano notes. During the instrumental part, in comes what sounds like a Mellotron, which is about as out-there as It’s a Game gets. (The album’s credits list nearly a dozen players without specifying any instruments.)

That leaves a lot of work for Frost’s voice, so it’s good to hear that when she laments, on “Playmate,” “I wanna find somebody to press against in the night,” she comes across as both lonely and lustful. She sounds appropriately resolved on “What’s the Use” and on the sign-off, “Lovin’ You Goodbye.” The latter is a relatively up-tempo number about acceptance in which she makes the line “I’m glad I had you/For what little time you could give” seem something other than pathetic—probably because, as the “I couldn’t leave without lovin’ you goodbye” chorus suggests, her acceptance was aided by an empowering pre-break-up scrump.

That Frost has now fully transformed her music from experimentation to traditionalism might not seem like something to be proud of. But that she’s done so without becoming any less engaging—well, even Liz Phair couldn’t pull that off.CP