Children of the Anachronistic Dynasty first recorded a demo, an independent cassette called Fingernails in 1986. It was recorded in Keenan's living room. While Horning played the guitar, Keenan sang, played bass and worked the drum machine. It is considered their "best-known recording. One song on the cassette, "Burn About Out" is considered to be in part an early version of the Tool song "Sober". The following year, they recorded a second EP called Dog House, a cassette sought after due to scarcity in copies. The three other members from Tex A.N.S., Tom Geluso, Stan Henderson, and Todd Horning were recruited to support Children of the Anachronistic Dynasty after Keenan asked them to return. Filmed on stage at the Kendall College of Art & Design, Children of the Anachronistic Dynasty appeared on a Grand Rapids public access channel in April 1987 performing a few songs off of Fingernails, including "Burn Out About." The airing also featured an interview with Keenan.

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