Their constantly changing music has challenged audiences and the record labels they have worked with, with one CMJ reviewer calling it "metal for recovering indie rockers".

Season to Risk toured constantly for their first 15 years, being booked as a young band on shows with Killdozer, Killing Joke, Prong, Fugazi, Corrosion of Conformity, Monster Magnet, and Unsane.

The self-titled debut Season To Risk (1993) features the songs "Snakes" and "Mine Eyes", and a cover of Neil Young's "Don't Cry".

Season to Risk wanted a darker sound that reflected their live performance, and recorded In A Perfect World (1995) during the Summer 1994 with Martin Bisi (Sonic Youth, Foetus, Swans).

The Shattering (2001) was produced by Bill Stevenson and Jason Livermore at the Blasting Room in Fort Collins, CO, and released on Descendents' label Owned and Operated Records.

Steve and Billy continued writing songs in a more melodic direction on several Roman Numerals albums and performing with Wade as Thee Water MoccaSins.

Duane Trower played guitar with Overstep, Ex-Acrobat, Olivetti Letter and built a new recording studio, Weights and Measures Soundlab, where he has produced many albums including Radkey, Giants Chair, Muscle Worship, and others.

In 2018, Season to Risk began releasing a remastered vinyl reissue series with indie labels and on their Bandcamp page[5] and toured, playing SxSW South By Southwest in Texas and Valley of the Vapors fest in Arkansas, sharing the stage with side project band Sie Lieben Maschinen.

Season to Risk began recording new music with Duane Trower at his studio Weights and Measures Soundlab in 2022, while they were reunited for shows with Cheer Accident.