Following several years fronting the punk band Terror of Tiny Town (its name borrowed from the 1938 film), Berner released his first solo EP, Light Enough to Travel (2000) on the Sudden Death Records label.

The Vancouver band The Be Good Tanyas covered the title track, and had some chart success with their version in England, which helped to kickstart Berner's career.

His first full-length album, We Shall Not Flag or Fail, We Shall Go On to the End (2003) featured the track "Volcano God", which has been covered by Finnish-German singer/songwriter Mäkkelä and Canadian singer/songwriter Wax Mannequin.

After his return, Berner released his second studio album, Whiskey Rabbi (2005) on Black Hen Music, with the help of Diona Davies of Po' Girl, on the violin, and Wayne Adams of Zolty Cracker, percussion.

In 2007, Berner released The Wedding Dance of the Widow Bride, a concept album with the theme of marriage, and second in his planned trilogy of klezmer records.

The song asserts that, in order to help pay for the games, the government of British Columbia closed a provincial coroner's office which investigated the deaths of children.

He stated at the time, "We're all trying to put out a vision of Jewish culture that's the opposite of the conservative, knee-jerk pro-Israel, judgmental b---s--- that's emerged in recent decades."

The album title is a reference to the old German folk tale about elderly farm animals threatened with death, who run away from their masters in the hope of achieving freedom by becoming Town Musicians.

In February 2019, Berner released a video for the Canadiana Grotesquica track "Super Subtle Folk Song" in response to the National Energy Board's second recommendation to approve the Trans Mountain pipeline expansion.

He is also close friends with American ukulele player Carmaig de Forest, and covers his compositions regularly on tour, and recorded his song "In the Year 2020" on his We Shall Not Flag or Fail, We Shall Go On to the End album.

[15] It was well-received, with Foreword Reviews writing, "The language blends the profane and poetic … Melodic and chaotic, with a wide range of voices, The Fiddler is a Good Woman creates an artist of complex character, unapologetically flawed and almost too real to be fictional.