Tobi Celeste Vail was born in Auburn, Washington, to teenage parents. Both her grandfather and her father were drummers. When she was young her parents moved the family to rural Naselle, Washington, where her father worked in a youth detention center. The family moved to Olympia, Washington, where Vail attended high school. The first concert she went to on her own was a Wipers show in 1984. In 1988, Vail left Washington to live in Eugene, Oregon. After a year, she returned to Olympia.
While still in high school, Vail volunteered at KAOS (FM), the campus radio station at The Evergreen State College. At KAOS, Vail was exposed to a wide variety of independent music. She served off and on as a disc jockey from age 15 to 21.
One of Vail's first bands was the Go Team, a punk project started with Calvin Johnson in 1985. The group released several cassettes and nine singles on the independent label K Records, mostly on the 7" vinyl format. Billy "Boredom" Karren was one of the rotating musicians who played with the Go Team, and it was in this band that he and Vail played together for the first time. The band toured the West Coast in 1987 as a two-piece, then added Karren for two U.S. tours, both in 1989. After the Go Team disbanded, Vail played in various project bands and made a record as the drummer for Some Velvet Sidewalk; she toured with Some Velvet Sidewalk during early 1990. Since the beginning of her teens, Vail had tried to form an all-girl band to "rule the world and change how people view music and politics", including a group named Doris, but none of the projects proved successful.
In 1989 Vail published the first issue of her feminist zine Jigsaw. When she published the zine, Vail was working at an Olympia sandwich shop with Kathi Wilcox who remembers being impressed by Vail's focus on "girls in bands, specifically," including an aggressive emphasis on feminist issues. While Kathleen Hanna was touring with Viva Knievel she came upon a copy of Jigsaw #2, finding resonance in Vail's "Boxes", a five-page article about gender. Hanna wrote to Vail and submitted musician interviews to be published in Jigsaw; this was the beginning of their collaboration. In Jigsaw, Vail wrote about "angry grrls", combining the word girls with the powerful growl of grr. Vail's third issue, published in 1991 after she spent time in Washington D.C., was subtitled "angry grrrl zine". Vail soon became dismayed with the male-slanted media coverage of the riot grrrl scene. Janice Radway notes that her copy of Jigsaw #4, also published in 1991, has many instances of the printed word "grrrl", but each one has been crossed out, "presumably by Vail, as a protest against the popularity of the term."
The final issue of the printed version of Jigsaw was published in 1999. In 2001, Vail began an online blog named Bumpidee. Vail used the Bumpidee site to publish Jigsaw #8 in the spring and summer of 2003, including writings by Alan Licht and Becca Albee. She moved the Jigsaw blog to its own domain in September 2008. In mid-2013, Jigsaw issues from the 1990s were archived at Harvard University as a research resource along with 20,000 other countercultural zines.
Vail met Kurt Cobain when he was hanging around with the Melvins in 1986. Cobain played guitar on one of the Go Team songs. Vail and Cobain briefly dated beginning in July 1990. The two discussed the possibility of starting a music project, and recorded a few songs together. Some of these songs ended up being Nirvana tracks. In October 1990 after Dave Grohl joined Nirvana, Hanna and Grohl started dating, making for two couples linking Nirvana to the new band Bikini Kill. Referring to the Teen Spirit deodorant brand that Vail once used, Hanna spray-painted "Kurt Smells Like Teen Spirit" on the wall of Cobain's bedroom. Cobain, unaware of the deodorant brand, saw a deeper meaning in the spray-painted phrase, and he wrote the song "Smells Like Teen Spirit" which became a monumental hit song for Nirvana. Cobain and Vail soon split but they remained friends.
In October 1990 Vail, Wilcox and Hanna determined to form a band, which they named Bikini Kill. Vail played drums and on some songs she sang. Through early 1991 Hanna and Wilcox swapped bass player and lead singer duties halfway through the set, and Wilcox also played guitar. After trying out a lot of female lead guitar players, none of whom seemed to fit, the band finally asked Karren to join as he was already known to Vail and a familiar figure in the Olympia music scene.
Soon after the band formed, they started a zine called Bikini Kill to promote the band and describe the band's social and political views. Hanna, Vail and Wilcox contributed articles to the zine. In Bikini Kill #1, Vail commented on the punk music scene and its overemphasis on males. She wrote about the "Yoko factor": the time when a male musician tells his girlfriend that she should not break up the band (comparing Yoko Ono's influence on the breakup of the Beatles) and that the girlfriend would never be as important to him as his band. Through the Bikini Kill zine and publicity for the band, Vail voiced her belief that the world would change for the better if the number of girls joining bands increased until it was equal to the number of boys.
Despite frequent mainstream media misrepresentation and serious violence at shows, they continued for several years and today are largely credited (along with Bratmobile) with starting riot grrrl, a movement that merged do it yourself (DIY) punk culture with feminism. The band Bikini Kill tried to reclaim feminism for the punk scene in an attempt to disrupt its male bias. The band fought against male aggression at their shows. Largely because of Hanna's leadership, Bikini Kill encouraged girls to stand at the front of the stage for solidarity as well as for protection from male aggression. Vail and the other members of Bikini Kill encouraged girls to start their own bands. The general idea that girls should create their own independent culture grew rapidly in popularity through a largely underground network of similar-feeling fans, artists, musicians and writers, and soon regular meetings started taking place, usually in punk houses like Positive Force. By the summer of 1991 the riot grrrl movement had coalesced, with Bikini Kill moving to Washington, D.C., for a year.
In 1992 while still involved with Bikini Kill, Tobi started the Frumpies in Washington, D.C., with Bikini Kill bandmates Wilcox and Karren, and also with Molly Neuman of Bratmobile and the PeeChees, and later Michelle Mae. The Frumpies were distinctly less overtly political in nature than either Bikini Kill or Bratmobile, with a different sound. The band toured the U.S. with Huggy Bear in 1993 and they toured Italy with noise rock band Dada Swing in 2000.
In 1993, Vail started Bumpidee, a low-cost method for unsigned bands to increase their listener base, using the distribution of cassette recordings of their songs. This was another embodiment of Vail's strong DIY principle. The name Bumpidee was chosen in honor of the children's television show Bumpity. One of the Bumpidee bands was Worst Case Scenario which included Justin Trosper and Brandt Sandeno—these two musicians found success in the band Unwound, retaining the DIY ethic from their Bumpidee exposure.
Vail ran the mail order department at Kill Rock Stars from 1998 to 2011, after working there part-time during 1992–1997. In addition to blogging through her Jigsaw website, Vail also posts as "Tabitha Says" on Tumblr, beginning in August 2008.
With her sister Maggie, Vail joined Alison Wolfe, Cat Power, and members of Sleater-Kinney to organize the first Ladyfest in 2000, a music, activism, and arts conference held in Olympia. The Vail sisters played the festival in a band named Frenchie and the German Girls. In keeping with Vail's DIY ethic, the Ladyfest founders turned the Ladyfest brand over to the public domain so that others could freely organize similar festivals.
In 2006-08, Vail drummed with the Old Haunts including on their final album: Poisonous Times. Vail has performed several solo shows, including one in Barcelona at Primera Persona in March 2012.
Vail started working as a freelance writer after graduating from the Evergreen State College in 2009. Her work has been published by NPR, Artforum, The Believer, Punk Planet & Maximum Rock-N-Roll. She currently writes a monthly column for eMusic and was recently published by The Feminist Press in the anthologies Pussy Riot: A Punk Prayer for Freedom and The Riot Grrrl Collection. Hanna commented upon Vail's song "Free Pussy Riot", written in support of the Russian feminist punk band Pussy Riot after three members were arrested in March 2012. The Punk Singer, a 2013 documentary about Hanna includes footage from three archival interviews with Vail. The film also includes archival footage of several Bikini Kill performances.
In February 2016, Vail issued a YouTube takedown request after a pro-Hillary Clinton video, utilizing the Bikini Kill song "Rebel Girl" began to go viral.
In mid-2004 Vail founded the band Spider and the Webs, with James Maeda on guitar and Chris Sutton on drums and bass. Vail sings and plays guitar, and she trades drumming roles with Sutton. Spider and the Webs played Ladyfest in 2005 in Olympia, and Vail spoke about the riot grrrl movement at other Ladyfest conferences held in Brighton and Madrid in October 2005, during a Spider and the Webs European tour. The band produced an EP in October 2006 on K Records: Frozen Roses, following a split EP with Partyline on Bristol, UK's Local Kid records. A (cassette) album was eventually released in 2015, also available as a download.