Group members Prince Po (poetry) and Pharoahe Monch began their career under the name Simply II Positive MCs. Originally, Po was the rapper and Pharoahe was a beatboxer, but after realizing his rhyming skill, Monch joined Po as MC. The duo caught the attention of prominent Hip Hop producer Paul C, who produced a demo for the group in the late 1980s. Paul was murdered in 1989, but the duo went on and signed a record deal with Hollywood Basic Records.
In 1991, the group released their critically acclaimed self-titled debut album, Organized Konfusion. The album was produced entirely by the duo, and featured only one guest appearance, provided by the group’s childhood friend, future D.I.T.C. member O.C., who appeared on the single „Fudge Pudge“. The album’s single, „Walk Into The Sun“, became a minor hit for the group, peaking at #15 on the Hot Rap Singles chart. The album itself didn’t manage to make any Billboard chart, despite high praise from numerous sources, including Allmusic, which granted the album a perfect 5 star rating, with reviewer Stanton Swihart stating that it is „arguably the underground rap album of the 1990s“.
The duo returned in 1994 with their second album Stress: The Extinction Agenda. This album was once more low on guests, featuring another appearance by O.C., and A Tribe Called Quest’s Q-Tip, who both appeared on the song „Let’s Organize“. The album’s lead single „Stress“ charted on the Hot Rap Singles chart, but the most famous song from the album is arguably „Stray Bullet“, a concept track which sees the MCs describing the travels of a stray bullet in first-person narrative. This album fared better commercially, but sales still never matched the wide acclaim.
Following the release of Stress, Organized Konfusion moved from Hollywood Basic to Priority Records. Their third album, The Equinox, was released in 1997. The album featured an ambitious concept, complete with numerous storytelling skits. Many saw the concept as a failure, which led to the album receiving less critical acclaim, when compared to their previous efforts. Led by the single „Somehow, Someway“, the album managed to reach higher on the Billboard charts than their last two albums.
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