"[4] Harris gave guitar lessons and performed in musical groups before he formed the duo Once Blue with singer-songwriter Rebecca Martin.

[6][7] The soundtrack featured new versions of his songs by Jones, Willie Nelson, Emmylou Harris, Feist, Cat Power, M. Ward, The Black Keys, Bright Eyes, Brad Mehldau and Rosario Ortega.

[8][9] Harris's 11th album, Sub Rosa, recorded in Rio de Janeiro, was released in July 2012[10] and features guest vocals from Conor Oberst, Melody Gardot, and Norah Jones.

[12] Other artists who have recorded Harris's songs include Smokey Robinson, George Benson, Pat Metheny, Kandace Springs, and Solomon Burke.

Songwriting collaborations have included Madeleine Peyroux, Melody Gardot, Maria Gadú, Maya Hawke, and Vinicius Cantuária.

Production credits include albums for Forro in the Dark, Sasha Dobson In 2017, Jesse started Cosmo, a group for only his instrumental compositions, with CJ Camerieri (trumpet, flugelhorn, and French horn), Will Graefe (guitar), Jeremy Gustin (drums), Benjamin Lazar Davis (bass), Michael Boshcen (trombone), and Harris (guitar).

Harris's album Aquarelle was recorded in Lisbon, Portugal, and released in September 2018, and features Gustin and Graefe, Ricardo Dias Gomes (bass, keyboards), Petra Haden, Valerie June, Sophia Brous, Thomas Bartlett, Rob Moose, Jesse Carmichael, Marcelo Camelo, and Jason Lader.