In the 1960s, Silliman attended Merritt College, San Francisco State University and the University of California, Berkeley, but left without attaining a degree. He has subsequently taught in the Graduate Writing Program at San Francisco State University, at the University of California at San Diego, at New College of California and, in shorter stints, at Naropa University and Brown University.

Silliman has worked as a political organizer, a lobbyist, an ethnographer, a newspaper editor, a director of development, and as the executive editor of the Socialist Review . While in San Francisco, he served on numerous community boards including the 1980 Census Oversight Committee, the Arson Task Force of the San Francisco Fire Department, and the State Department of Health's Task Force on Health Conditions in Locale Detention Facilities. After living in the San Francisco Bay Area for over 40 years, Silliman moved to Chester County, Pennsylvania in 1995 where he resides with his wife Krishna and two sons, Colin and Jesse. Silliman works as a market analyst in the computer industry.

Silliman was a 2003 Literary fellow of the National Endowment for the Arts & a 2002 Fellow of the Pennsylvania Arts Council as well as a Pew Fellow in the Arts in 1998. Silliman is one of the poets memorialized in Berkeley's Addison Anthology, a walk containing plaques recognizing poets and authors in his home town.

While Silliman has come to be associated with the Language poets, he came of age under the sign of Donald Allen's New American Poetry (1960) . Silliman was first published in Berkeley, in 1965. In the 1960s he was published by journals associated with what he calls the School of Quietude, such as Poetry Northwest, TriQuarterly, Southern Review and Poetry. Silliman found such early acceptance to be a sign of the lack of standards or rigor characteristic of that literary tendency and began looking for alternatives.

Silliman edited a newsletter, Tottels (1970—81), that was one of the early venues for Language Poetry. However, it was "The Dwelling Place," a feature of nine poets that Silliman did for Alcheringa. Ethnopoetics in 1975 that Silliman himself describes as his "first attempt to write about language poetry". In 1976 & '77, he co-curated a reading series with Tom Mandel, at the Grand Piano, a coffee house in San Francisco's Haight-Ashbury, continuing a series originally founded by Barrett Watten. This series was followed by one at the Tassajara Bakery, co-curated with Bob Perelman, and a series combining poets with performance artists at The Farm, co-curated with Jill Scott.

Silliman's mature critical writing dates to the early/mid-1970s when he was asked to discuss his thinking about the role of reference in poetry, leading to the essay "Disappearance of the Author, Appearance of the World," which first appeared in the journal Art Con. Soon thereafter he edited a special issue of the magazine Margins devoted to the work of poet Clark Coolidge and began to give talks and contribute essays on a regular basis thereafter. As was mentioned above, Silliman was influenced by (and subsequently has written extensively on) the "New American Poetry", referring to the poets who first appeared in Donald Allen's groundbreaking anthology The New American Poetry 1945—1960. Today, those same (but then relatively unknown) poets included in this anthology are now recognizable or precedent figures in the current cultural landscape.

In 1986, Silliman's anthology, In the American Tree, one of the foremost collections of American language poetry, was published by the National Poetry Foundation.

1970's

• Crow (1971)
• Mohawk (1973)
• Nox (1974)
• Ketjak (San Francisco: This Press, 1978)
• Sitting Up, Standing, Taking Steps (1978)

1980's

• Legend (1980, with Bruce Andrews, Charles Bernstein, Ray DiPalma, Steve McCaffery)
• Tjanting (1981; new edition from Salt Publishing, 2002)
• BART (1982)
• ABC (1983)
• Paradise (1985)
• The Age of Huts (1986)
• In the American Tree: Language, Realism, Thought (National Poetry Foundation, 1986; second edition, 2001: anthology)
• Lit (1987)
• The New Sentence ( 1987, criticism)
• What (1988)

1990's

• Manifest (1990)
• Leningrad (1991, with Michael Davidson, Lyn Hejinian, Barrett Watten)
• Demo to Ink (1992)
• Toner (1992)
• Jones (1993)
• N/O (1994)
• Xing (1996)
• MultiPlex (1998, with Karen Mac Cormack)
• ® (1999)

2000's

• Sunset Debris (2002, ubu ebook) from The Age of Huts
• 2197 (2004, ubu ebook) from The Age of Huts
• Woundwood (2004)
• Under Albany (Salt Publishing, 2004: memoir)
• The Chinese Notebook (2004, ubu ebook) from The Age of Huts
• (contributor)The Grand Piano: An Experiment In Collective Autobiography (with Bob Perelman, Barrett Watten, Steve Benson, Carla Harryman, Tom Mandel, Rae Armantrout, Kit Robinson, Lyn Hejinian, and Ted Pearson) (Mode A/This Press, 2007: ISBN 978-0-9790198-0-X)
• The Age of Huts () (University of California Press, 2007)
• The Alphabet (University of Alabama Press, 2008)