Works are primarily typescripts unless otherwise noted. Most manuscripts appear to be essays and stories submitted to magazines. Also included in this series are issues from the three small magazines O'Brien published and edited through his father's art gallery, Art, The Eaglet, and The Observer, which covered cultural and aesthetic topics. In addition, there are several book-length manuscripts, book outlines and notes, materials for a book-keeping system that O'Brien had patented called Budget Books, and scrapbooks containing clippings of O'Brien's Chicago Daily News columns, "Footnotes" and "All Things Considered."