41. Dr. Octagon, Dr. Octagonecologyst (1996)
Label: Bulk Recordings
In case you were wondering what kind of doctor Kool Keith became when he took to the stethoscope for this twisted indie-rap classic, the title makes it clear. It's not easy becoming a gynecologist-you have to go to med school, a four-year residency program, and then pass the board exams—but Doc Oc is a dedicated, dedicated man when it comes to ladies and their nether regions.