2000s
In 2000, Mann released Bachelor No. 2, released on SuperEgo, which included some songs from Magnolia and new material. Also that year, she and her husband formed a concept called Acoustic Vaudeville, a mixture of music and stand-up comedy; among the comedians joining them for shows were Janeane Garofalo, Patton Oswalt, and David Cross.
In 2002, Mann released Lost in Space, an album which featured art by Seth. The following year she released Lost in Space Special Edition, which featured 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 2004, Mann released Live at St. Ann's Warehouse, a live album and DVD recorded at a series of shows in Brooklyn.
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, contained illustrations which reflected Mann's interest in boxing. She trained with the boxing trainer Freddie Roach; the album's title is derived from a boxing move in which one arm is used to hit the opponent, causing him to "forget" about the other, which is then used to deliver a harsher blow. The following year, Mann received a Grammy for "Best Recording Package" for the album's artwork (shared with Gail Marowitz).
In 2006, Mann released One More Drifter in the Snow, a Christmas album featuring both covers and new songs. The album's iTunes version replaced "Christmastime" (a duet with husband Michael Penn) with a cover of Joni Mitchell's "River", and "Clean Up for Christmas" from The Forgotten Arm; an updated version of the CD was released two years later with the Joni Mitchell cover.
In 2008, Mann released @#%&*! Smilers, which featured Grammy-nominated artwork by Gary Taxali. The album debuted on the Billboard 200 at #32, and on the Top Independent Albums chart at #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." The music video for the song "31 Today", directed by Bobcat Goldthwait, featured comedienne Morgan Murphy.
In 2009, Mann announced that she was working on a musical based on her album The Forgotten Arm, but later stated that it was put on hold due to similarities to The Fighter.
In 2011, Mann joined the 9th annual Independent Music Awards judging panel to promote independent musicians. She was also an inaugural member of the panel in 2002.
In 2012, Mann released Charmer, an album which featured a duet with James Mercer of The Shins.
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