He currently plays guitar for Crowbar. He formerly played guitar in Down, resigning in 2013, and he also played bass for Valume Nob, but resigned in 2006, citing he was unable to commit the time needed to give it full justice. In February 2005, Windstein formed Kingdom of Sorrow with Jamey Jasta of Hatebreed. Their debut album, including guest artists, was released on 19 February 2008. Windstein began his musical career in 1985 as a guitarist for a cover band called Victorian Blitz, and in 1988 joined a hardcore punk band called Shell Shock as a vocalist and guitarist.
Windstein played guitar for the cover bandVictorian Blitz in 1985. Other members included Sid Montz, with whom Windstein would play again in Crowbar and Valume Nob; Kevin Noonan, guitarist from 1989 to 1993; and bassist Danny Theriot of Metairie, Louisiana.
Having left Victorian Blitz, Windstein joined the New Orleans' premiere hardcore punk band Shell Shock as their guitarist and vocalist. With Windstein in the band they began to play more of a crossover thrash style rather than straightforward hardcore punk, as it better suited Windstein's vocal style and a two-guitarists line-up. When the band was recording a new album called "No Tomorrow", their guitarist Mike Hatch committed suicide. Kevin Noonan replaced Hatch for the final Shell Shock show in 1988, and the band became what now is Crowbar.
After the collapse of Shell Shock in 1988 due to the suicide of guitarist Mike Hatch, the band enlisted Kevin Noonan and carried on as Aftershock, which played a mixture of hardcore punk and doom metal. Under that name they released a demo in mid-1989, but then renamed themselves WREQIUEM when bassist Mike Savoie (who would later direct music videos for Crowbar, Down, and Pantera) left the band and was replaced by Todd Strange. In 1990 they renamed themselves to The Slugs, and after a demo in mid-1990, the band collapsed. Windstein considered becoming the guitarist for Exhorder. But Windstein and Strange reformed the band, with Craig Nunenmacher as the drummer, and Kevin Noonan on guitar. The band renamed themselves Crowbar in mid-1991.
Crowbar was originally signed by Mark Nawara to Pavement Music and released "Obedience Through Suffering" in 1991. Windstein's childhood friend Phil Anselmo (who at the time was in Pantera) produced their next effort, a self-titled album released in 1993. The album went on to achieve international success with songs such as "All I Had (I Gave)", "Existence is Punishment", and a cover of Led Zeppelin's "No Quarter". MTV's Headbangers Ball began to play the music video for "Existence Is Punishment", which was also featured on Beavis and Butt-head. Following that success, the band toured with Pantera. Together, the bands partied heavily, and footage of these events appears on Pantera's "Home Video 3" and Crowbar's "Like Broken" video, in which Windstein dressed up as the Hulk. In 2001, Crowbar went on hiatus, because Windstein concentrated on other bands. With Windstein's returned, Crowbar released Lifesblood for the Downtrodden in 2005, and two years later released a live DVD called "Live:With Full Force". The band released Sever the Wicked Hand in 2011 and their latest album Symmetry in Black was released on 26 May 2014.