That says something about how hip-hop evolves as a genre - it's not Fitzgerald's fault that the genre he loves best moves so fast, and getting an indie documentary finished on a shoestring can be a lengthy process. But you wouldn't notice how dated the film feels if it didn't have more serious organizational problems. Freestyle mainly wants to be a documentary about the history and mechanics of freestyling, but its loose-limbed, impressionistic structure too often makes the film drift away from the point. Freestyle bounces from interviews with members of early-'70s Beat-poet-styled hip-hop pioneers the Last Poets to brief (and unconvincing) attempts to tether freestyling to Baptist church preachers and John Coltrane's improvisations. Brief interludes about the history of early hip-hop in the Bronx, female rappers, and the mainstream rap industry take on worthy subjects, but they draw energy away from the subject at hand.
When it sticks to the point, though, there are some powerful, illuminating moments. A stunning clip of a young Notorious B.I.G. freestyling on a Brooklyn street in 1987 shows that he'd mastered his stentorian flow by the time he was a teenager. The best segments about MC Supernatural, who gets the most screen time, are the ones where he discusses his learning process (essentially, memorizing a rhyming dictionary) and the pressures involved in staying ahead of competitors in battle raps. And Supernatural's nemesis, Chicago rapper Juice, cuts an amusingly controversial figure - everybody who talks about him is quick to wonder if he's committed the cardinal sin of writing his freestyles.
Unfortunately, Fitzgerald doesn't spend nearly enough time on any one subject to give a clear picture of what role he believes freestyling plays in hip-hop - depending on who's talking, it's a subgenre of hip-hop, a stepping-stone in a hip-hop career, or hip-hop itself. Most often, it comes off as hip-hop's version of jamming, which is capable of brilliance or teeth-gnashingly dull self-indulgence. Watch a few unknowns rattle off some off-beat ruminations about the last time they had sex or the other guy's flaws, and you'll appreciate why Mos Def and B.I.G. made it to the big leagues. But there's too little evidence that freestyling in itself deserves even the short 75 minutes allotted for this film.
Run time: 60 mins
In Theaters: Friday 14th April 2000
Distributed by: Organic Films
Contactmusic.com: 2.5 / 5
Rotten Tomatoes: 89%
Fresh: 16 Rotten: 2
IMDB: 7.6 / 10
Director: Kevin Fitzgerald
Producer: Henry Alex Rubin
Starring: Muhammad Ali as Himself, Planet Asia as Himself, Bahamadia as Herself, Akim Funk Buddah as Himself, Eluard Burt as Himself, Myo Campbell as Himself, John Coltrane as Himself, Darkleaf as Himself, Mos Def as Himself, Kirby Dominant as Himself