In June of 1999 the Insane Clown Posse (ICP) release their fith Joker's Card album entitled: The Amazing Jeckel Brothers. The Amazing Jeckel Brothers debuted at #4 on the Billboard Charts. Considering the lack of Radio/MTV play and other media support, this was a major achievement. The Amazing Jeckel Brothers was quickly certified platinum.
1999 & 2000 juggalos saw the Insane Clown Posse touring throughout the county, both in larger arenias, including an appearance at the Woodstock, and covering lesser markets at small venues. The Insane Clown Posse (ICP) also appeared on the cover of serveral magazines, including Alternative Press, with that issue going on to break all AP sales records. They released a successful comic book series through Chaos Comics. The Insane Clown Posse (ICP) also started an independent wrestling promotion called Juggalo Championshit Wrestling (JCW), which went on to become the second highest grossing promotion in the U.S.
Insane Clown Posse (ICP) and Psychopathic Records made significant and groundbreaking expansions during this time, all setting the stage for the long-awaited sixth and final Joker's Card album.