
I'm hoping to get a new audience sometime, so I thought I might do an entry for those who want to get into the Expanded Universe. I've read mostly novels, and some of the comics, so I'm just basing this on my experience...the informed will no doubt correct me if I'm wrong on the details.
Where to start? First off, pick up any recent Star Wars novel (as in something made in the past year or so, like a paperback version of
Outbound Flight by Timothy Zahn, for example) in a book store and flip through the first few pages to see the Star Wars Novel Timeline. That lists out every novel and when the events in that novel happened. Now...I'll give some of my recommendations.
Between Empire Strikes Back and Return of the Jedi, four words:
Shadows of the Empire. Get that novel. It rocks. Period.
After Return of the Jedi,
The Truce at Bakura is an option, but it's just so boring to me. What I recommend, if you want to know about how the Rebels retook Coruscant, is the
X-Wing series, written by Michael Stackpole and later by Aaron Allston. Brilliant stuff.
My first novel was one from the
Young Jedi Knights series, called
Crisis at Crystal Reef. It's a story that takes place years later, but it's still interesting to see the next generation.
The Thrawn Trilogy by Timothy Zahn is an absolute essential--
Heir to the Empire,
Dark Force Rising, and
The Last Command. I believe that's where we're first introduced to our dearly beloved Mara Jade.

But stuff happens in between the X-Wing series and the Thrawn trilogy. The Courtship of Princess Leia, while an unusual story, is important, as we get to see how Han finally takes his last steps towards tying the knot with Leia. Oh, and how could I forget the Jedi Academy Trilogy by Kevin J. Anderson?
Jedi Search,
Dark Apprentice, and
Champions of the Force. Those are also essential, as they show Luke Skywalker in his efforts to restore the Jedi Order and his search for potential new Jedi candidates.
I, Jedi by Michael Stackpole is a cool tie-in with both the Jedi Academy stories and the X-Wing series. That was the second novel I read, and it made me fall in love with Stackpole's writing style. It's a great read, one of the best, I'd say.
And a must-read comic series is
Dark Empire, where Luke Skywalker turns to the dark side, in service of, shockingly, the resurrected Emperor Palpatine. Whoa.
The New Jedi Order is the more recent stuff--20 novels in the series, the notables are the first and last,
Vector Prime and
The Unifying Force, with many greats in-between, like
Dark Tide I & II,
Star By Star,
Traitor,
Edge of Victory I & II, and the like. Obviously it's a good idea to read them in order, but those are some of my favorites.
The Dark Nest Trilogy happens after the New Jedi Order, and it's a great read. Plenty of good setup for the now-running Legacy of the Force series; I recommend every novel in the Legacy of the Force series, they're just great stuff.
Now, going in the other direction, novels in the Prequel era...
I highly recommend
Darth Maul: Shadow Hunter by Michael Reaves. Brilliant and interesting look at Darth Maul.
Cloak of Deception adds further to the political setup before the Battle of Naboo (or Episode I).
Rogue Planet is an interesting story between Episodes I and II--and has a reference to the New Jedi Order series, which you won't get until you read the New Jedi Order stuff.
Clone Wars (between Episodes II and III)--my #1 pick is
Shatterpoint by Matthew Stover. He is pure brilliance in this one, taking the lid off of Mace Windu and showing how the guy thinks.
Jedi Trial by David Sherman and Dan Cragg is a raw, gritty look at the harsh reality of war and how Anakin Skywalker distinguishes himself in battle and learns to be a competent commander; it's a hard read at first, but it gets good after awhile.
Yoda: Dark Rendezvous is definitely one of the best--it got me through jury duty. A nice exploration of the dark side and Count Dooku's relationship with Yoda. And a little more explanation of the whole 'why some Jedi disappear when they die'. Yoda has a great illustration in there to explain the whole process, how it works. I suppose it wouldn't be right to fail to mention the MedStar Duology by Michael Reaves and Steve Perry. Funny, great work--it's Star Wars meets M*A*S*H, as many have probably called it before me.
Labyrinth of Evil by James Luceno is a great prelude to Episode III, written with the right sense of urgency and a command of all the relevant Star Wars history. The
Revenge of the Sith novelization, also by Matthew Stover, is, in my opinion, even better than the movie (and since ROTS is my favorite, that's saying a lot). It's so good, I actually didn't like the movie at first because it wasn't enough like the novel. Another great work by James Luceno is
Dark Lord: The Rise of Darth Vader, which is good enough to be called Episode 3.5, I would say, describing the post-Episode III events with great urgency and giving you those conversations you always wanted to hear between Vader and the Emperor.
...I think that sums it all up. Those are the high points I could think of. I had to consult the timeline myself to remember some of them. Pick a place to start, and start reading. Oh, I have to add my thumbs-down list...
The Truce at Bakura (I mentioned that already)
The Cestus Deception (but it wasn't so bad--just...a lot of it was boring)
The Bounty Hunter Wars (
The Mandalorian Armor, Slave Ship, and Hard Merchandise) - avoid at all costs!! It's a waste of valuable time. I recommend the
Republic Commando books by Karen Traviss instead.
The Approaching Storm (ooh, awful, awful stuff...prelude to Episode II, so boring)
I'm not one to talk, and if you want to read the above-mentioned ones, that's fine; I can't write half as well as those folks anyway, though I've certainly tried fan fiction. It's just opinion. Well, get to reading, enjoy, and May the Force be with you!
Chris2OneBee