Roskies was born in 1948 in Montreal, where his family emigrated 1940 from Vilnius.

His grandmother, Fradl Matz, ran the famous Matz Press in Vilnius, a publishing house that produced prayer books, bibles and popular Yiddish literature. His mother Masha (born in 1906 in Vilnius) and her family were forced to flee Europe for Montreal, via Lisbon and New York in 1940. Her Montreal home became a salon for Yiddish writers, actors, and artists as Isaac B. Singer, Melech Ravitch, Itsik Manger, Avrom Sutzkever and Rachel Korn.

After learning in Yiddish secular schools in Montreal, Roskies was educated at Brandeis University, where he received his doctorate in 1975.

In the 1970s Roskies was a member of the Havurat Shalom, a small egalitarian chavurah in Somerville, Massachusetts, best known as the first such lay-led Jewish community in the United States.

A prolific author, editor, and scholar, he has published numerous books and received awards. Roskies now resides in New York City.

One major focus of his work is the Holocaust. On this topic he published 1971 Night Words: A Midrash on the Holocaust, one of the first liturgies on the subject ever to appear. Night Words has entered its fifth edition, was adapted into Hebrew, and was recently reissued by CLAL as an audiocassette.In 1984, Harvard University Press published Against the Apocalypse: Responses to Catastrophe in Modern Jewish Culture, which won the Ralph Waldo Emerson Prize from Phi Beta Kappa and has since been translated into Russian and Hebrew. A companion volume, The Literature of Destruction, was published by the Jewish Publication Society in 1989.In 2007, Dr. Roskies served as the J. B. and Maurice C. Shapiro Senior Scholar-in-Residence at the United States Holocaust Memorial Museum. He is currently under contract with University Press of New England to produce Holocaust Literature: A History and Guide.

A second focus of his work, since 1975, has been the folklore of Ashkenazic Jewry. He coauthored The Shtetl Book: An Introduction to East European Jewish Life and Lore. Awarded a Guggenheim Fellowship in 1985, Dr. Roskies began studying the modern Jewish return to folklore and fantasy. The fruits of his labor are the edition of The Dybbuk and Other Writings by S. Ansky (Yale, 1992) and the book A Bridge of Longing: The Lost Art of Yiddish Storytelling (Harvard, 1995). A thirtieth-anniversary edition of The Shtetl Book, meanwhile, was put out by Ktav in 2005.

A third focus of Dr. Roskies' work is The Jewish Search for a Usable Past, the title of a book of related essays published in 1999. Then, in 2008, he finally tried his hand at writing a memoir. Yiddishlands: A Memoir (Wayne State University Press) is the story of modern Yiddish culture as told through the lens of family history and the medium of Yiddish song. A CD of his mother singing accompanies the volume.

In 1981 (with Dr. Alan Mintz), Dr. Roskies cofounded Prooftexts: A Journal of Jewish Literary HistoryHe has served since 1998 as editor in chief of the New Yiddish Library, published by Yale University Press.A member of the editorial board of the Posen Library of Jewish Culture and Civilization, he is hard at work on Volume IX, encompassing the years 1939 through 1973.