While working at Ruby-Spears he began self-publishing "Jim", an anthology of comics, dream art and free-form writing which he described as an "autojournal". In 1986, Woodring was introduced by Gil Kane to Gary Groth of Fantagraphics Books. "Jim" was published as a regular series by Fantagraphics starting in 1986, to critical acclaim if less than spectacular sales, and Woodring became a full-time cartoonist. "Frank", a wordless surrealist series which began as an occasional feature within "Jim", became his best-known work, eventually spinning off into its own series in 1996. Most of the content of the first of the two volumes of "Jim" were collected as "The Book of Jim" in 1993, which was subsequently ranked as #71 on The Comics Journal's100 best comics of the century list.