Alkaline Trio was formed in 1996 with Skiba as the frontman. Since then, the band has released nine full-length albums over two decades. Skiba also recorded albums with side projects including Heavens and theHell, as well as two full-length solo albums with his backing band, the Sekrets.

Following Tom DeLonge's second departure from Blink-182 in early 2015, Skiba began touring with the pop-punk trio, then joined the band permanently later that year; he has since recorded two albums with them.