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The first song on Joan of Arc’s recently released third album, Live in Chicago, 1999, opens on the morning of a romantic hangover. The guitars stretch. The keyboards yawn. The drums snap, unfocused, in slo-mo. Singer Tim Kinsella is still in bed with a deep case of the blues—he doesn’t sing into a mike so much as mumble into his pillow. The song, “It’s Easier to Drink on an Empty Stomach Than Eat on a Broken Heart,” sums up his newfound monogamy—emphasis on mono. A “Catholic girl” has played hard-to-get for one last night. And it’s hard to wake up from that, take a shower, and head to your day job.

In the song, Kinsella keeps turning over his pillow in confusion and finding new meanings for everything: Kisses are meant for good-byes, not sweetness; late nights are just late nights, not romantic holidays; and “I love you,” Kinsella discovers, means “I owe you a friendship.” Kinsella feels the hurt bad enough to turn himself into Jesus and the girl into Judas: “Jesus knew only Judas loved him enough to know just how to fuck him.” The song ends with Kinsella mumbling again until he seemingly falls back asleep.

You don’t hear Kinsella again until three minutes and 17 seconds into the next track, “Who’s Afraid of Elizabeth Taylor?” He’s still in his bed mumbling—except a little louder than before. The song itself is just as quiet: Todd Mattei plucks his acoustic guitar with his fingers lost on the same three notes. The drums drop into the mix like pebbles into a puddle. Jeremy Boyle plugs in the white space with a warped keyboard that sounds like those tornadoes in Twister.

These are overcast songs of lovelorn gloom: tone poems that spread out, rumble a bit, but mostly just loom over the listener in one big gray mood. This isn’t much of a surprise considering that Joan of Arc don’t necessarily compose songs; it makes albums meant for taking in all at once. The tracks float into each other; the chords don’t change for entire albums.

The band’s first two albums, A Portable Model Of and How Memory Works, are meant as post-rock meditations on pop culture and romance, referencing Leonardo DiCaprio and Fiona Apple and a lot of Kinsella. After starting outside—conversational, heady, and plain-spoken—they move slowly to the bedroom.

Live in Chicago, 1999 goes in the other direction: Kinsella opens up with the post-breakup bedroom scene and works his way out of the sheets, his stuttering, groaning voice stuck in snooze mode for the first four songs. It takes him a while to get confident enough to just sing.

The songs themselves aren’t just little stories but meta-songs filled with ironies, allusions, and enough hypertext to make David Foster Wallace proud—tales meant for re-reading. When he pleads for quiet on a street corner (he’s really on a street corner, with the traffic around him), his voice is broken up amid a ferocious drum roll. When he says, “O girl let’s betray our talents/If you’re not bound you’re only on the rebound,” you get the feeling he could be singing not just about love but his own band. Everything is fair game, even covering a Scott Walker tune, “Thanks for Chicago, Mr. James,” in full-tilt croon.

It’s gutsy stuff when you consider that most rock and punk tunes are obsessed with teen culture. And when they aren’t, when rockers—anyone from Yes to Gastr del Sol—try to say something bigger, they usually sound pretentious and dull. But Kinsella, along with a handful of others—namely Elliott Smith and, sometimes, Bikini Kill’s Kathleen Hanna—is writing songs for his own age and getting it right. Kinsella’s demographic happens to be a tough one, with steel on its toes, bell hooks in its backpack, and Ritalin in its veins. Think of all the post-punk energy zapped by memorizing textbooks and checking out one’s own feelings, which tend to collide in fucked-up ways.

In this context, Kinsella just sounds like a postgraduate adult trying to make sense of his life—one cluttered with French films, romance, political correctness, and a lot of questions. It happens that Kinsella graduated with a degree in women’s studies from DePaul University, but he’s still trying to figure out women.

Joan of Arc’s first two album titles read like computer manuals, but Live in Chicago, 1999 carries the pretentious air of trying to make a statement. The publicity sheet on Jade Tree’s beautiful Web site claims as much, exclaiming that although it is not a live album per se, it follows the line of those other crucial live albums of our time—Cheap Trick’s and Dylan’s. You’re supposed to know you’re getting something important.

If that doesn’t catch you, the liner notes back up the imprint of “art.” The booklet shows a scene-by-scene re-creation of Godard’s Weekend, a gross-out movie concerning one long bloody traffic jam, upper-class wankers, and cannibal hippies. The French-film theme continues down to the band’s nom de plume; it had the taste to copyright its music under Jean-Pierre Leaud (who played the little boy in Truffaut’s Four Hundred Blows). If you were trying to navigate ’90s romance, wouldn’t you cling to the last true romantic rebels?

The standout track, “Me (Plural)” (which, in Kinsella-speak, means a duet with singer Jen Wood), declares his forensics on ruined love perfectly. Over simple minor piano chords, Kinsella and Wood sing together: “I’m confusing me for who you think I am…Maybe everything we meant to be di’n’t [sic] need to end so mean.” Few have diagnosed a bum relationship so well. By the end of the album, the clouds hang as heavy as when he woke up, but that lingering hope from “Me (Plural)” survives. Kinsella spends the rest of the album in cerebral travelogue: dueling acoustic instrumentals, unrequited pleas pocked with grunts and groans, and riffs on sexual politics. All toward the very ’90s impossible ideals: finding a girlfriend and restoring your self-esteem. Like all good hypertext authors, Kinsella ends the album with a call for another listen: He bellows, “It’s over/Begin again.” He could be saying the same for his love life. CP

Joan of Arc plays La Casa June 25.