After the monotonous Psyche Intangible (Metaforensics, 1998), he crafted one of his best songs, Lacking Precipitation (originally titled Simulated Snow on an Anticon compilation) and several instrumental interludes on Psyche Continuum (1999).

Those two albums and Termination Dubs (2000) were compiled on Almost A Dot On The Map - The Psyche Years - 1996-2002.

Songs I Hate and Other People Moments (2001) contains three of his signature songs (Grimey Inks the Moment, One World Lost and All New Mad Max Song), the 14-minute Work in Progress, a lengthy rap over ever-changing instrumental (including melancholy flute and sax solos), and the 35-minute The Canada Project, an odd experiment of collective rapping, 35 minutes shared with fellow rappers Adam "Adeem" Arnone, Buck 65 and Sage Francis over spartan beats.

He turned into an electronic composer of instrumental hip-hop on the five-song EP The Secrets That Houses Keep (2001), which contains five instrumental experiments, notably the sitar-driven The Secrets That Houses Keep that samples Paul Horn, Oregon and Ravi Shankar. The border between vocal and instrumental tracks was blurred in the wasteland sculpted by his producers in the 39-minute jam Duration Project, collected with the EP on Duration (Cease & Desist, 2002). In that piece, recorded with bassist Lukas Pierce, guitarist Mike Boudreau and saxophonist Seth Von Handorf, Sixtoo abandoned the verbose mode for an instrumental symphony in 16 parts, loosely inspired by DJ Shadow's sinister atmospheres. ### II cicada-like electronic noise, jazz trumpet and turntable scratching V soliloquies and dialogues in hallucinated atmospheres IV Jon Hassell-esque trumpet-driven alien soundscape VI languid cosmic drones VII sitar drone and mechanical repetition of his vocals over an industrial beat VIII a hypnotic xylophone-driven scratch-infected march IX a melancholy and nostalgic synth melody XI a catchy harpsichord tune that seems to be culled from an old Paul Mauriat record but turns into a sinister hard-rocking theme (XIII) which turns into an obsessive pulse and siren, XV romantic and exotic saxophone solo over a convoluted beat quoting Sun Ra, Miles Davis and Alice Coltrane

His venture into instrumental hip-hop continued with the double LP Antagonist Survival Kit (Vertical Form, 2003), split between five raps and five instrumentals. Towering over the rest is the 19-minute The Mile-End Artbike, de facto an exploration of trance via propulsive beats and subliminal effects.

Villain Accelerate's Maid Of Gold (2003) documents a collaboration with Stigg of the Dump.

The mostly instrumental Chewing On Glass And Other Miracle Cures (Ninja Tune, 2004) completed Sixtoo's evolution towards digital composition by focusing on live instruments. The result is akin to DJ Shadow's funkiest and jazziest efforts. The three parts of Boxcutter Emporium are quite different in nature: angst-filled dub-tinged electronic music, a repetitive fuzz-like effect with insistent drumming and sparse bass notes, a melancholy noir-tinged organ melody. Sixtoo runs the gamut from the psychedelic jazz-rock of Sidewinders to memories of Canterbury's progressive-rock in The Honesty Of Constant Humna Error, from the sleepy exotic Snake Bite to the trance-like Closing Day Sale. The most disorienting piece is the confused aggregate of sonic events around an elegiac guitar of Horse Draws Carriage. The only drawback is that the album is fragmented in too many brief pieces, none of which stands up as a memorable composition. It leaves the impression of a vulnerable and insecure musical persona. The nine-minute Storm Clouds & Silver Linngs (featuring Damo Suzuki on vocals) tries to reach for a higher standard, but the lengthy bluesy recitation over frenzied drumming and atonal guitar fails to attain any transcendent meaning.

Jackals and Vipers in Envy of Man (2007) contains 13 untitled beat-based pieces that sound more like leftovers than full-fledged experiments

Squire decided to kill the Sixtoo project and created the new personas of Megasoid with the mixtape Tank Thong Re (2008) and then of Prison Garde with the albums Systeme Hermes Volume One (2011) and Occultsystem (2014). He also produced Isaiah "Toothtaker" Camacho's music, notably the album Sea Punk Funk (2012).