[DEAR DIARY HIP-HOP] When people tell me they're not really feeling the Portland hip-hop scene, I point them to Cloudy October. The Portland MC resides at the corner of massive ego and crushing anxiety. He is painfully honest. He is the Woody Allen of rap.

Case in point: "Hairline Fracture," Cloudy's ode to his own receding hairline. It takes a brave MC to tackle this subject, and the fact that October combines self-deprecating one-liners ("Suckas always telling me they're gonna push my wig back/ Motherfucker Mother Nature just did that") with a dancehall reggae beat on his new free-download record will only further endear him to his small but loyal local fanbase.

Though Cloudy encourages fans to boo at his live shows, he's not built on self-hatred. Elsewhere on The Metal Jerk, he's the president of his own fan club. "Play" and "Live @ Pioneer Square" are packed with creative boasts (though I'm not sure "Style, simple and plain/ I got game/ Check out my emaciated frame" fully qualifies). And on "Name Yourself," we start to sense the depth of self-awareness behind that sense of humor. "When I was born I was given a Eurocentric name/ When I got a little wiser I decided to change it," he explains by way of biography. That partially explains Cloudy's strange fit of a legal name, Kizzy Yokomura, but the lines to come tell us even more about the man behind the moniker. "And with this lust for learning I'm a real go-getter/ And I didn't need religion or prison to know better."

Cloudy ends the album in true Woody Allen fashion (The Metal Jerk's last words are, "He's bigger than me. All over. He has a job and everything"). But between the searing beats—think Shabazz Palaces meets Dan the Automator—and the fascinating, revealing lyricism here, Cloudy really has nothing to be ashamed of.

SEE IT: Cloudy October's The Metal Jerk is out now as a free download at Fieldwerk.com.