He relocated to Los Angeles in 1988 to pursue a career in interior design and set construction, and formed Tool with Adam Jones shortly thereafter.

[7] His mother suffered a paralyzing subarachnoid hemorrhage due to a ruptured cerebral aneurysm in 1976 when Keenan was 11, and this incident would later serve as the inspiration for songs such as Tool's "Jimmy," "The Patient," and "Wings for Marie," as well as A Perfect Circle's "Judith.

In addition to completing a rigorous math and English curriculum, Keenan wrestled, ran on the cross country team, and sang in the glee club.

[17] He also (with future Tool bandmate Danny Carey) performed live and recorded with Green Jellö between 1990 and 1993, playing guitar and performing backup vocals as the voice of one of the pigs on the band's hit song "Three Little Pigs" on their debut album Cereal Killer, and appearing in the music video for "Slave Boy" on the band's follow-up LP 333.

Fronted by Keenan, the eventual lineup included guitarist Jones; his neighbor, drummer Danny Carey; and bassist Paul D'Amour, who would later be replaced by Justin Chancellor.

The video was deemed "too graphic and offensive",[22] and was withdrawn by MTV after a few airings due to "a symbolic dealing with the sensitive subject of child abuse".

During the hiatus, Keenan went under the alias "Gaylord C." while collaborating with Tim Alexander of Primus and Mike Bordin of Faith No More on "Choked",[25] a track on the 1997 drumming compilation Flyin' Traps.

[26] The band members were outspokenly critical of peer-to-peer file sharing networks, due to the negative financial effect on artists dependent on success in record sales.

Billboard 200 albums chart in its debut week,[32] and Tool received their second Grammy Award for the best metal performance of 2001 for "Schism".

Their subsequent 2004 album, eMOTIVe, was primarily composed of covers, except for the singles "Counting Bodies Like Sheep to the Rhythm of the War Drums"—a song inspired by "Pet" that was originally released on Thirteenth Step—and "Passive".

[49]When asked, in an interview for Spin that same month, about the possibility of another A Perfect Circle album, Keenan stated, "Maybe, someday, a song on a soundtrack.

Puscifer was once advertised as a side project with Danny Lohner, who had formerly performed live with Nine Inch Nails, but has since been "formed as a manifestation of [Keenan's] creative subconscious"[56]—interpreted to mean that the name is now a pseudonym for his solo work.

[58] When comparing the project to Tool in an interview with Rolling Stone, Keenan described it as his "attempt to make music to inspire people.

[67] In addition to the merchandise available on the band's online store, Keenan has also made available locally roasted coffee, art, and limited edition collectibles.

[68] On February 13–15, 2009, Keenan debuted Puscifer at the Pearl Concert Theater in Palms Casino Resort in Paradise, Nevada, with a cabaret-style show so abstract it is not easily described.

Keenan—who has had previous experience with this type of entertainment, having fronted a similar show in Los Angeles before achieving fame with Tool[70]—went on to add that "you just can't really describe it, you just have to see it, then it makes sense.

"[71] Featuring an ever-changing lineup of artists including Milla Jovovich and Primus drummer Tim Alexander, the show was originally said to have a long-term residency at the Pearl;[72] however, Keenan later revealed that it was to be only a two-show performance.

[76] A primary purpose of Keenan's lyrics for Tool involves a desire to connect with the listeners on a personal level, encouraging them to look within themselves for self-identity, understanding and reflection.

After dropping the fan to the ground with a gentle hip toss, Keenan, continuing to sing, wrapped himself around the man's back into a rear naked choke.

"[87] His appearance with Tool has included the Mohawk hairstyle,[82] wigs, Kabuki masks, bras, tights,[88] and his entire body in blue paint.

21 in Hit Parader's 2006 list of "Heavy Metal's All-Time Top 100 Vocalists",[94] and his style of singing has been considered influential to Pete Loeffler of Chevelle and Jared Leto of Thirty Seconds to Mars.

[101] Keenan is featured in several segments of Mr. Show,[102] most notably in the Ronnie Dobbs sketch presented in the first season in which he plays the lead singer of the then-fictitious band "Puscifer".

"[15] In the mid-90s, responding to requests for Tool to perform in benefit shows, Keenan created "Free Frances Bean" tee-shirts to represent his own platform.

[16][111] He is also a partner of Stronghold Vineyards,[114] "an 80-acre site dedicated to producing affordable wines in the state",[115] located in the small, unincorporated area known as Kansas Settlement in Sulfur Springs Valley, Arizona.

[117]His previous wines were named after relatives of the Chiricahua Apache chief Cochise who lived in the area where the vineyard is located,[118] and were produced at Page Springs Cellars, owned by Keenan's business partner.

[119] During the fall season of 2008, Keenan and his Stronghold Vineyards partner Eric Glomski promoted his wine with signing sessions at Whole Foods Markets in California and Nevada.

[124] The film, which includes appearances from Tim & Eric, Patton Oswalt, and Milla Jovovich, was shown at the Noise Pop Festival on February 25, 2010.

It investigates why people create and listen to music, and features Keenan, Jason Schwartzman, Kurt Loder, Nic Harcourt, Juliette Lewis, and Elijah Wood.

Keenan has a son, Devo, who sang backing vocals on A Perfect Circle's Thirteenth Step,[130] and was later credited as the cellist on Ashes Divide's Keep Telling Myself It's Alright.

[111] Brazilian Jiu-Jitsu is one of Keenan's pursuits, as shown when he took down a fan who ran on stage in the middle of a performance and put them in a rear naked choke, and he studied under Rickson Gracie.