Chicago band Cheer-Accident, initially just the duo of keyboardist/drummer Thymme Jones (ex Illusion of Safety) and vocalist Jim Drummond, debuted with a number of independently produced cassettes. Drummond left and in 1986 bassist Chris Block and guitarist Jeff Libersher joined Jones. The EP Life Isn't Like That (1986) was followed by the gargantuan Sever Roots Tree Dies (1988), featuring lots of instruments and studio tricks, produced by guitarist Phil Bonnet, who then became a permanent member.

Steve Albini produced the EP Dumb Ask (Neat Metal, 1989) whose highlight is the dissonant double-guitar assault of Phil Bonnet and Jeff Libersher. By this time the sound had transitioned towards the kind of brainy progressive-rock pursued by latter-day King Crimson.

Babies Shouldn't Smoke (Neat Metal, 1991) was an even harsher and disjointed recording.

The Why Album (1994) was instead a collection of pop songs.

Jones, always hyperactive on the Chicago scene, then formed You Fantastic and joined avant-punks Dot Dot Dot; and released the solo piano albums While (Perdition Plastics, 1996) and Career Move (Perdition Plastics, 1997). Meanwhile, Cheer-Accident recruited bassist Dylan Posa.

Despite Cheer-Accident's pedigree, the mostly instrumental Not A Food (Pravda, 1996) likes to follow into the footsteps of Frank Zappa's dadaistic circus (King Cheezamin, the nine-minute Evan Had A Half-Life). The bold counterpoint and textures used to derail the jokes are descendants of Slint's school of avant-rock. The album's weak point is a stubborn and a little self-indulgent recycling of progressive-rock cliches (the 11-minute 30 Seconds of Weightlessness).

Piano and organ largely replace guitars on the 72-minute 14-track tour de force Enduring The American Dream (Pravda, 1997). Often, the keyboards are used as percussion instruments, like in Steve Reich's minimalist scores. Nonetheless, "songs" such as Metaphysical indulge in melodic romanticism. What has remained the same is the abrupt rhythm changes (the 13-minute Desert Song), and the ironic attitude towards songwriting (Dismantling the Berliz Waltz). The opening Vacuum is just one 5-minute drone.

The 52-minute song of the EP Trading Balloons (2000), recorded in 1997, is a worthy, corollary to the demented collage style of the album.

Bonnet, a well-known producer for whom Cheer-Accident was an intellectual passtime, died in February 1999 at the age of 38.

Thymme Jones released another solo album, While (Perdition Plastics, 2000), a set of five minimalist piano quartets.

Cheer-Accident's first post-Bonnet album, Salad Days (Skin Graft, 2000), is another fantastic excursion in the realms of creative music. The 11-minute Graphic Depression (originally composed in 1981) and the 19-minute Salad Days rank among the band's most daring ventures, trascending both prog-rock and math-rock and coining a new form of abstract composition. Insomnia and Post-Premature are cubistic pieces built by warping melodies into geometric shapes and by assembling collages of disconnected sounds. The album suffers from the way it was composed (the other members overdubbing tracks that Bonnet had barely sketched), but it still provides moments of intriguing theory. The scores are complex in the tradition of Frank Zappa and Soft Machine.

Jones also released the "home recording" Variations On A Goddamn Old Man (Pravda, 2001).

Gumballhead The Cat (Skin Graft, 2003) sounds, instead, like Cheer-Accident's less innovative work, a mere routine that surveys the themes and styles they are more familiar with.

Continuing the stylistic zig-zag, Introducing Lemon (Skin Graft, 2003) marks, for the most part, a glorious return to their most abstract and discordant prog-rock roots. The 22-minute suite The Autumn Wind is a Pirate is a summation of the band's prog-rock and post-rock ambitions, a powerful potion of Yes, Frank Zappa and King Crimson for the Tortoise generation, a stylistic tour de force that is the real reason for the album to exist. The other 22-minute monolith, Find, that closes the album, is basically, a medley of ballads bridged by convoluted instrumental passages, but it could have been edited down to half its length; and the shortest songs (with the exception of the pretty Smile) are filler of the worst kind.

By now Cheer-Accident had become the vehicle for Thymme Jones' music, who surrounded himself with different collaborators on each album. What Sequel (2006) was his "pop" album: a collection of relatively straightforward melodic ditties. Unfortunately, they are marred by his vocals, not the most tuneful in the business.

More changes of line-up led to Fear Draws Misfortune (Cuneiform, 2009) with Alex Perkolup on bass and Jeff Libersher on guitar, a much more complex album that harked back to Introducing Lemon. Sun Dies is an oddly syncopated chant with Carla Kihlstedt of Sleepytime Gorilla Museum on vocals, that draws from both African music and Art Bears, while the arrangement of saxophone, flute, violin and keyboards evokes early King Crimson. Blue Cheadle is another surreal lullabies, sung by a mixed choir and accompagnied by loud keyboards and guitars. Marketa Fajrajzlova sings The Carnal Garish City, a disjointed piece that features saxophonist Dave Smith of Poi Dog Pondering and cellist Fred Lonberg-Holm. Humanizing The Distance is just a confused, hysterical fanfare for an ensemble that includes cornet, bassoon, saxophone, trombone, tuba. The longer track, Your Weak Heart, starts out as one of Jones' piano-driven pop ballads before the piano plunges into a frantic jazzy improvisation, soon joined by keyboards and reeds.

Cheer-Accident's 17th album No Ifs Ands or Dogs (Cuneiform, 2011) featured the consolidated line-up of Carmen Armillas (vocals but everybody takes turns at singing), Thymme Jones (keyboards, brass, synth, drums), Jeff Libersher (guitar, keyboards, trumpet, bass), Alex Perkolup (bass, guitar), Dudley Bayne (keyboards, trombone), Andrea Faught (keyboards) and Lise Gilly (saxophones). The obvious shift is towards melody. The pop aria of Drag You Down (despite shivering metallic guitar and dense and disorienting arrangements) opens the album in a friendly vein, followed by the falsetto soul melody and march-like tempo of Barely Breathing and by the Merseybeat-style refrain of Cynical Girl, while the album ends with the choral singalong Provincial Din. Other songs don't push quite that far, drenching the strained vocal harmonies of Sleep in Frank Zappa-esque keyboards and adorning Trial Of Error with pounding industrial beats and emphatic synth lines. The Cheer-Accident heritage (the limping jagged pseudo-jazz counterpoint) is still in full display in the instrumentals This Is The New That and Salad Dies.

After a six-year hiatus they returned with Putting Off Death (Cuneiform, 2017), containing the eleven-minute Language Is and played by a new line up around the founding trio of Armillas, Jones and Libersher (Dante Kester on bass and keyboards, Mike Hagedorn on trombone, Cory Bengtsen on baritone sax, Beth Yates on flute, Julie Pomerleau on violin, Joan Morrone on french horn, Ross Feller on tenor sax, Rob Pleshar and Todd Fackler on tubas), which was followed by two brief albums, Fades (Cuneiform, 2018) and Chicago XX (Cuneiform, 2019).

Vacate (2024) was a tribute to easy listening music of the 1950s and 1960s.