I've spent the past week reading Samuel Delany's early fiction in roughly chronological order, starting with The Jewels of Aptor, then continuing on to The Fall of the Towers trilogy, Babel-17, and Empire Star (which Vintage has conveniently packaged together). (And yes, I realize I've missed The Ballad of Beta 2 -- I misplaced my copy and so decided to continue on until I figure out which pile of books it got buried under.)
The only one of these books I'd read before was Babel-17, the first Delany novel I ever encountered, having been introduced to his work through the stories "Time Considered as a Helix of Semi-Precious Stones" and "Aye, and Gomorrah" in anthologies. It's been ages since I read any of Delany's pre-Dhalgren books, and the experience has been illuminating.
Delany's early work is the writing of an extraordinarily intelligent and talented young man, but The Jewels of Aptor and The Fall of the Towers really only possess interest because of what they show us about Delany's progression as a writer, since they contain so many nascent versions of characters, images, situations, and ideas that would gain more subtle and complex presentation later. Even a book like Babel-17, which demonstrates notable breakthroughs in Delany's technique, is minor in comparison to many of the novels that would come later.
The surprise for me in the reading so far has been Empire Star, a novella originally published as an Ace Double with Tom Purdom's The Tree Lord of Imeten. The story was a surprise because I had never seen much reference to it, and so always assumed it was minor and not of much interest. In fact, I preferred it to Babel-17 -- the writing is more compact and efficient, the prose is mostly light instead of leaden, the situations suffer less from Delany's tendency to romanticize poets and criminals (because that romanticization is treated with at least a hint of irony here), and the structure is openly recursive and metafictional in a way that allows the story to feel as rich as any of Delany's novels up to that time.
Empire Star is a bildungsroman and a space opera about a character named Comet Jo, who begins as an uneducated and provincial young man on a primitive planet, then leaves home and ends up affecting the fate of a good portion of the universe. It contains many of the themes that have been consistently prevalent in Delany's work -- questions of freedom, language, culture, perception, art -- and while he would later find more complex and nuanced approaches to these themes, here they seldom weigh the tale down as they do in all of his earlier novels (and some of the later ones, for that matter). Empire Star also shows Delany becoming better at exposition; Babel-17 had been superior to the previous four books, but Empire Star is nearly free of any moments where background information is presented through awkward and obvious dialogue. The tone of the writing is different, too. In addition to the sometimes-hardboiled/sometimes-purple prose common to Delany's early work, there is a new playfulness and even irony to the writing -- for the first time, Delany is not just trying to write a better version of a traditional SF formula, he is letting himself chuckle at the fun such a formula allows. After all, a book called Empire Star by a writer named Muels Aranlyde (yes, an anagram) was mentioned in Babel-17, where it was said to be one of the "Comet Jo" books and "a lot of fun". (This dialogue occurs on a page of Babel-17 devoted to a discussion of the intersections and complications of fiction and reality. And Muels Aranlyde is a character in Delany's Empire Star along with Comet Jo.)
I've sometimes wondered what a good introduction to Delany's work might be for someone who doesn't want to jump right in to the densest of his books. The short stories are certainly a good place to start, but they don't particularly prepare a reader for many of the complexities of the novels. Perhaps Nova or The Einstein Intersection. Today, though, it seems to me that Empire Star offers the most effective and appealing introduction to so many of the ideas and techniques Delany would employ later.