Taylor joined Slipknot in 1997 and began working on his first demo tape with the band around early 1998. The end result was the Slipknot Demo which featured the tracks Spit It Out and Wait and Bleed among others. The album was passed on to famed nu metal producer Ross Robinson who ultimately helped them to get signed to Roadrunner Records. The band began working on their major label debut Slipknot in 1998 and it was released the following year. The album's lyrics were penned by Taylor and reflected many of his early struggles and experiences from growing up and living in Des Moines, as well as tackling other topics including religion, social commentary and murder. The band embarked on a lenghty touring cycle in support of the album, and gradually built a large fanbase while gaining commercial and critical acclaim. However, the band also became engulfed in controversy over its image and music, in no small part due to Taylor's song lyrics (Rick Anderson of Allmusic noted that "those lyrics that are discernible are not generally quotable on a family website, suffice it to say that the members of Slipknot are not impressed with their fathers, their hometown, or most anything else).

The band broke their intensive tour cycle to re-enter the studio to record their sophomore album, releasing Iowa in 2001. Taylor again provided all the album's vocals and lyrics, and the band gained further critical and commercial acclaim.

Following speculation among fans and within the media about the band's future, Taylor re-grouped with Slipknot in late 2003 with producer Rick Rubin to write and record their third album. The sessions were initially de-railed by various member's personal issues (including Taylor's heavy drinking, which had been a progressively worsening problem since Slipknot's first album was released), but eventually the band released Vol. 3: (The Subliminal Verses) in 2004. The album marked a massive commercial breakthrough for the band, gaining significant airplay, high chart positions in a number of countries, album sales in the millions and a Grammy award for the single Before I Forget. Around this time, Taylor recognised that his drinking was a serious issue and managed to overcome the problem.