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Daniel Kahn was born on September 11, 1978, in Detroit, Michigan. He attended the University of Michigan, where he studied Theater, Playwriting, Poetry and Politics. After graduating, Daniel moved to New Orleans where he was first introduced to modern Jewish music. He then went on to live and perform in Detroit, New York and Michigan.

Daniel Kahn coined the word "Verfremdungsklezmer", meaning "alienation klezmer music", to describe their music, in reference to Bertolt Brecht's theory of Verfremdungseffekt. The group describes their music as "a mixture of Klezmer, radical Yiddish song, political cabaret and folk punk", and it has been compared to the music of Tom Waits and Woody Guthrie.

Some of the songs are written by Kahn, but many are adaptations of poems and songs by Jewish authors such as Mordechaj Gebirtig, frequently with socio-political themes. The Painted Birds have had songs about varied political topics, such as Nakam, a group of Holocaust Survivors who conspired to kill Germans in revenge for the Holocaust, and the government response to Hurricane Katrina, set to the tune of Dos Lid fun Titanik, a 1912 Yiddish song originally about the sinking of the Titanic. Kahn also sings songs by Franz Josef Degenhardt (Die alten Lieder), Heinrich Heine (Die alten Lieder), Bertolt Brecht, (Judenhure Marie Sanders and Denn wovon lebt der Mensch?), and Kurt Tucholsky (Rosen auf den Weg gestreut) as well as a Yiddish version of the classic Lili Marleen. In 2016 he translated Leonard Cohen's "Hallelujah" into Yiddish, which he has occasionally sung at concerts since then.

He sings in English, German and Yiddish, often mixing several languages in one song. Translating lyrics has been an interest and source of inspiration. The Painted Birds have previously collaborated with Russian singing Vanya Zhuk as well as Michael Winograd, Paul Brody and Dan Blacksberg.

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