|Raquel Welch played the title character in the (terrible) movie version of Myra Breckinridge.|
Myra Breckinridge (1968)
by Gore Vidal
I would expect more than one Gore Vidal novel on the 1001 Books list. Maybe if it was assembled by an American editorial staff. Norman Mailer, another hugely popular American novelist from the same generation as Vidal, doesn't get a single book on the list. In Vidal and the list's defense, he was better known for his non-fiction writing and general public/celebrity persona than any specific work of fiction. However, to the extent that he did write a memorable novel, Myra Breckinridge is it, generally credited with the first literary depiction of a "post-op" (male to female) trans.
Myra Breckinridge is a satire of "Hollywood culture," Myra arrives in Hollywood as the "widow" of her "dead" male persona (Myron.) As the book is written, this fact is eventually revealed as a modest surprise for the reader. For a contemporary reader, Myra's trans status is communicated before you start, either from a foreword designating Myra a classic of trans lit, or packaging Myra with it's twin, Myron, published several years later.
To be clear, Myra Breckinridge is only revolutionary in terms of the explicit depiction of a post operative trans. The literary theme of gender fluidity is as ancient as myth, and 20th centuries authors like Virginia Woolf explored related concepts a half century before Breckinridge was published in 1968. Although it shocked when it was initially published, today the sexual material is best described as "mildly bawdy." On the other hand, his jabs at left-coast culture are prescient, including the first mention of the California bred tradition of including "Like" before every statement. "Like, I'm drowning, can you help me?" is one memorable quote from Myra in the book.
There is also an early depiction of "60's style" orgy complete with weed and a lot of good lines about classic Hollywood film culture, again courtesy of Myra. What there isn't is plot, or a deep understanding of the psychology of the trans protagonist. In fact, Myra Breckinridge ends with an incredibly insensitive return by Myra to status as "Myron" after his fake boobs are removed while she is in recovery after an auto accident. It's that ending that has likely diminished the reputation of Myra Breckinridge for subsequent generations of readers.