#1 Tales of the Jedi
7,000 - 3,986 years BBY
You can't go much farther back than these graphic novels, which go back even before the Old Republic. Perhaps the most attractive part of this series is the chance to see the Ancient Sith Empire, a civilization of Sith far more numerous than in the times of Palpatine and Vader. The Jedi librarian Odan Uur, one of my favorite EU characters, makes his cameo in the first books of this series. This also chronicles the mortal life and fall of Exar Kun during the Great Sith War, 4,000 years before he posseses Kyp Duron and wreaks havok on Luke Skywalker's Jedi Academy. You also get a glimpse into the lifestyle of Ancient Jedi on the planet Ossus, when practices such as loving/emotional attachment and multiple apprentices were not yet forbidden. This makes the merit of the "dogmatic" ways of prequel-era Jedi seem much less convincing.
I can't wait for this period of time to be expanded on!
#2 Knights of the Old Republic (video game)
3,956 years BBY
This is one of the best Star Wars video games out. Being an RPG, you are relatively free to custumize your character and experience in terms of lightsabers, force powers, and allegience (lightside or darkside). You can also customize your team. All the while, the story remains essentially the same: you are the Sith Lord Darth Revan, who, having had your memory wiped by the Jedi Order and unable to remember your dark past, are on a mission to stop your old apprentice, Darth Malak, from harnessing the power of an invincible fleet. A word to the cannon-obesessed: the "true" ending to this game is Revan remaining loyal to the Jedi and defeating Malak. Another nice touch for this game is to read the Knights of the Old Republic graphic novel series, which features events during the Mandolorian War which lead up to this game. The sequel to this game, KOTOR II: The Sith Lords, is fun and interesting, but not nearly as story-driven as the first.
#3 Darth Bane: Path of Destruction by Drew Karpyshyn
1,000 years BBY
This book, the first of a trilogy, is absolutely fantastic. First, you get to see what the Sith were like before the "rule of two"- one master, one apprentice. You also get to see just how ancient Sith were trained. Trust me, it's brutal! During this book, the Jedi and the Sith are embroiled in the War of Light and Darkness and, all the while, Bane plots his takeover of the Sith Order, one betrayal and massacre at a time. Finally, the philosophical foundation of this book is intriguing and creative. Delving deep into the mind of Bane and his fellow Sith, you will come to understand the true nature of the dark side, and why it is a power that should only be shared by two.
Path of Destruction is a part of the Bane trilogy, Rule of Two being the second, but less engaging, book and Dynasty of Evil scheduled for release this October, 2009.
#4 Jedi Apprentice Series by Jude Watson (#1 by Dave Wolverton)
44 -34 years BBY
This may be a 20 book scholastic series, but it is well worth your time (and very little money). This series chronicles the adventures of a young Obi-Wan Kenobi as a padawan under Qui-Gon Jinn. Did you know that Qui-Gon had a previous padawan? Ever wonder why spirit Obi-Wan comments to Yoda that he, too, was too old for training when he began? The answers are here, as well as the very foundational philosophies and teachings of the Republic Jedi.
#5 Darth Maul
32 years BBY
Nothing like some good old dark side mayhem. And believe me, Darth Maul brings the pain! It's amazing Maul is so popular, espeically when his time in the Star Wars movies was so short (thanks, Obi). This is a very good origin story and one of the first appearances on the timeline of the Black Sun Criminal Organization- who, unsurprisingly, are no match for Maul.
#6 Darth Maul: Shadow Hunter by Michael Reaves
32 years BBY
Michael Reaves is one of my favorite SW authors, and I'll tell you why: every one of his books/series that I have read have taken place in different times and places. Yet, with the help of one or two common characters, all form a comprehensive story. This is the very first one and features everybody's favorite baddy, Darth Maul, as the key villain. If you read only one of Reaves' books, I recommend this one.
#7 The Republic Commando Quadrilogy by Karen Traviss
The Clone Wars: 22-19 years BBY
Once thing that I love about Karen Traviss is that, in every book of hers that I've read, she really challenges the way I think about the characters of the Star Wars Galaxy. This is especially so for the Republic Commando Quadrilogy, which takes place throughout the Clone Wars. If you read these, prepare never to look at Clones the same way, ever again. On top of that, she does a great job of highlighting the inconsistencies of conventional Jedi wisdom, such as attachment and the righteousness of their role as generals in the Clone Wars. This series is also a wonderful source to learn about Mandalorian (i.e. Boba Fett's) culture
I'm looking forward to her follow-up series, Imperial Commando, with the first book being released this October, 2009.
#8 Shatterpoint by Matthew Stover
21.5 years BBY
Now I don't know about you, but I love me some Mace Windu. Discover Mace's Korun roots in this exciting Clone Wars adventure to save his old padawan, Deepa Billaba! But before he can save her, he must overcome the malignant nature of the jungle that surrounds him at every turn. Just one question: Why's he gotta be from a jungle, Mutha F*&%$ !?
#9 Dark Rendevous by Sean Stewart
19.5 years BBY
Ever wondered what would happen if Yoda went to the dark side? Well so does Count Dooku. And if you read this book for any reason, read it for the final confrontation between Yoda and Dooku. Top that with lots of classic Clone Wars action and cameos from Asajj Ventriss, and you've got yourself a winner.
#10 Dark Lord: The Rise of Darth Vader by James Luceno
19-18.5 years BBY
Vader didn't become the cold, "more machine than man" Dark Lord we know from the Classic Trilogy over night, even after he donned the suit. James Luceno really seems to tap into that easily forgotten fact. I really love books that bring everything together. And after the dramatic events of Revenge of the Sith (Ep. III), this book is where you really get some closure. While we all know now how Anakin physically became Vader, James Luceno does a great job of finishing the emotional and spiritual transformation of Anakin Skywalker to Darth Vader.