Meanwhile, he performed with various improv comedy troupes around Chicago, including ImprovOlympic (where he studied with Del Close) and the Free Associates.

After Dave Eggers's magazine McSweeney's began publishing his work, Pollack began appearing in shows with Eggers, John Hodgman, Sarah Vowell, Zadie Smith, David Byrne, Arthur Bradford, James Flint, They Might Be Giants, M. Doughty, and many others before parting ways with McSweeney's in 2003.

The Neal Pollack Anthology of American Literature, a collection of short satires of literary pomposity, was originally published by McSweeney's in 2000.

It won the 2001 Firecracker Alternative Book Award for best independently published fiction[1] and led to Pollack being named a "Hot Writer" by Rolling Stone.

Designed to look like Harry Smith's Anthology of American Folk Music, the album is a bizarre if entertaining mishmash of styles.

HarperCollins put the album out in 2002 as part of a boxed set of Pollack's "collected recordings," including an hour-long disc of Def Poetry Jam parodies and a fake interview with John Hodgman.

Unlike his previous arch satires, Alternadad is a straightforward, if humorous memoir of his early days as a "cool" parent in Austin, Texas.

A marked departure from his previous work, Pollack wrote Jewball, a serio-comic noir set in the world of 1930s Jewish basketball players, as a tribute to the days of classic American crime fiction.

In September 2012, Amazon's Thomas & Mercer mystery and thriller imprint published Pollack's novel, Downward-Facing Death as part of its new Kindle Serials program.

Pollack's novel, Repeat, a romantic comedy with a time-travel element, was published by Amazon's Lake Union Press in March 2015.