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Pity Supernatural. There is never a good time to market a freestyle rap album, if only because the market for it doesn’t exist. Even in the arty world of Mr. Lif and Jean Grae, freestyling is seen as just another line on the résumé. But freestyling is Supernatural’s résumé. His impromptu openings for KRS-ONE, and his live battle with Juice Crew all-star Craig G, made him a legend (although he lost). Of course this was before a battle disintegrated into a gaggle of rappers exchanging death threats and boasts of cuckolding via Hot 97.

Two of Supernatural’s mic fights (including the Craig G gem) are among the improvised cuts collected for The Lost Freestyle Files, his debut album. Also included are various freestyles from Sway and Tech’s Wake-Up Show and the Stretch Armstrong and Bobbito Show. Thematically, Supernatural differs very little from standard underground rappers. Freestyling on “The Live Show,” he boasts, “Each and every time that I flip it/You can say I’m poetical, black, and gifted/Uplifted from a whole different plane/Make sure you never forget my name.” Also mixed in are a few unimprovised tracks, the best of which, “Work It Out,” features the Jurassic Five and Dilated Peoples.

Despite the cameos and production credits from the underground heavies featured on Files, Supernatural is still faced with a Herculean labor. In addition to just being good, he has to convince the listener that freestyling is an art deserving of attention. But haphazardly organized and pulling from some of Supernatural’s more marginal efforts (a Kazaa search will net better), Files never manages to make you believe that freestyling is more than something college cats do after imbibing bong hits and Boon’s.

The live clips are especially disappointing. Minus the adrenaline and immediacy of a live crowd, Supernatural’s battle with Craig G (“Clash of the Titans”) and his bout with Juice (“Get Ready to Rumble”) are both unmoving. Then on “The Live Show,” Supernatural attempts to assure the crowd that he’s freestyling by picking objects out of the audience to rap about. But without a visual connection, the parlor trick falls flat.

The album’s biggest flaw is that Supernatural almost solely freestyles about, well, freestyling. Such an insular approach is about as captivating as continuously watching an artist painting himself in the act of painting. Had Supernatural bothered to improvise lyrics about larger, external concepts, or even simply his own life—friends, love, family, anything besides rap—he would have instantly had a more interesting album.

But Files never aspires to such lofty heights, probably because hip-hop’s threshold for content beyond boasts is appallingly low. Moreover, underground acts, despite their purist proclamations, have actually aided this perception by consistently releasing above-average rap primarily concerned with dissecting below-average rap (Dilated Peoples, anyone?). For every Majesticons or OutKast, there are 10 MCs obsessed with self-aggrandizement and the act of MC’ing. Improvising about the same topics redundant MCs write about isn’t enough to differentiate Files from the pack. For a Supernatural album to succeed, it would have to be a broader, deeper rap album that would approach lyrical improv as rigorously as Charlie Parker did his instrumental wanderings. Instead, Files opts for the shortcut, making its most notable feature not improvisation but a lack of ambition.