In 1983, Mann co-founded the new wave band 'Til Tuesday with Berklee classmate and boyfriend Michael Hausman (who went on to manage her solo career). In 1985, the band released Voices Carry, the debut album with the title track inspired by the band's guitarist, Robert Holmes', relationship with his wife. It won the MTV Video Music Award for Best New Artist.

In 1986, the band released Welcome Home, their second album. In 1987, she sang vocals with Geddy Lee on the single "Time Stand Still" by rock band Rush from their 1987 album Hold Your Fire. She also appeared in the music video for the song.

In 1988, the band released Everything's Different Now, their third and final album. Shortly after its release, Mann said that she was much more pleased with it than the debut, primarily because she felt it made more of a personal statement about her life. The band broke up in 1990 when Mann left to start her solo career.

n 1993, Mann released her debut solo album, Whatever, which sold modestly but met with critical praise. In 1995, Mann released I'm With Stupid, her second album, through Geffen Records which, like her debut, garnered positive reviews but modest commercial success.

In 2000, Mann released Bachelor No. 2, released on SuperEgo, which included some songs from the 1999 film Magnolia and new material.

In 2002, Mann released Lost in Space, an album which features art by Seth. The following year she released Lost in Space Special Edition, which features a second disc containing six live recordings (including a version of Coldplay's "The Scientist") as well as two B-sides and two previously unreleased songs.

In 2005, Mann released The Forgotten Arm, a concept album set in the 1970s about two lovers who meet at the Virginia State Fair and go on the run. The Joe Henry-produced album, which was recorded mostly live with few overdubs, contains illustrations which reflected Mann's interest in boxing.

In 2008, Mann released @#%&! Smilers, which features Grammy-nominated artwork by Gary Taxali. The album debuted on the Billboard 200 at number 32 and on the Top Independent Albums chart at number 2. @#%&! Smilers was met with mostly praise, with Billboard stating that it "pops with color, something that gives it an immediacy that's rare for an artist known for songs that subtly worm their way into the subconscious... Smilers grabs a listener, never making him or her work at learning the record, as there are both big pop hooks and a rich sonic sheen."

In 2010, Mann joined the 9th Annual Independent Music Awards judging panel to promote independent musicians. She was also an inaugural member of the panel in 2001.

In 2011, Mann participated on the 10th Annual Independent Music Awards judging panel, marking a consecutive year and third overall appearance as a judge with the organization.

In 2012, Mann released Charmer, an album which features a duet with James Mercer of the Shins. Two singles were released from the album - the title track, which featured a music video directed by The Best Show's Tom Scharpling; and "Labrador," which featured actor Jon Hamm and references to Mann's music video work with 'Til Tuesday.

In January 2017, Mann announced Mental Illness, her ninth solo album. The album's lead single, "Goose Snow Cone," was released on the same day. On March 27 Mann performed the song with Jon Batiste and Stay Human on Late Show with Stephen Colbert. The album was released on March 31, 2017; with Mann releasing the album independently.

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