"Well-read" for this person then has a number of connotations: a familiarity with the monuments of Western literature, an at least passing interest in the high-points of world literature, a willingness to experience a breadth of genres, a special interest in the work of one's immediate culture, a desire to share in the same reading experiences of many other readers, and an emphasis on the writing of the current day.
The following 100 books (of fiction, poetry, and drama) is an attempt to satisfy those competing requirements. After going through several iterations of the list, one thing surprised me: there are not as many "classic" books that I associate with the moniker well-read, and many more current books than I would have thought. Conversely, to be conversant in the literature of the day turned out to be quite a bit more important than I would have thought.