With the exception of recording and appearing with close friend Kid Congo Powers and New York duo Sister Boy, Annie started a hiatus from music in 1990.
Being in her words 'driven insane by the hues' during a period of living in Mexico, the New Yorker returned home determined to teach herself painting, something which she had dabbled in previously, by devoting a full year of average 16-hour days.
Employing every medium with the exception of oils, her work has been described as having a "naive style", which is "figurative, metaphorical and surrealistic, with a strong emphasis on color; often combining tortuous, expressionistic cityscapes with Biblical imagery".
Little Annie returned full-time to music with an EP, Lullaby, cowritten with Larry Tee, and "Diamonds" was produced by Joe Budenholzer and Christoph Heemann released in 2002 by Drag City.
Her next album to follow would be the first of her more piano /string section-based works; Songs from the Coalmine Canary, released on the Durtro/Jnana label, was co-produced by Antony Hegarty and Joe Budenholzer (of Backworld).
[14] In 2011, Little Annie became the singer of the Italian band Larsen appearing on the albums La Fever Lit 2010 and Cool Cruel Mouth (Tin Angel).
In 2017, she guested on Hifi Sean's album FT on the track "Just Another Song", which she also wrote, and her first book of artwork, Meditations in Chaos, was published by Timeless Ed (Toulouse, France).