I’m assuming you mean the EU? Ooh boy. I’ve been using the timeline of Legends books and the timeline of canon books on Wookieepedia but, as you may notice, the Legends timeline has just so many books in it. The list is absolutely massive (if you’re also looking for comics and short stories, that’s a different list), so I’ll try to break it down a bit for you, starting with Legends.
The first eras, Before the Republic and Old Republic, are just so ancient that I’ve never been personally interested in them. Dawn of the Jedi: Into the Void, the Old Republic series, and the Darth Bane series are probably the most popular books from back then, and together they make up most of those eras.
The Rise of the Empire era is something I’m much more familiar with. The Jedi Apprentice series makes up a good chunk of it, and it’s one I would personally recommend (although I’ve been known to read anything involving Obi-Wan). The Clone Wars and Republic Commando series are both ones I’ve heard recommended but haven’t yet read, as well as the Last of the Jedi series. There are several great individual books in this era, some of which read like extra episodes of The Clone Wars – a few that come to mind are Rogue Planet, The Approaching Storm, and Kenobi. This era has a whole ton of worldbuilding details, so it’s definitely worth going through. It also has the three prequel trilogy books which, while I do love the movies, are better than the movies. For the record, I would sell my soul for the Revenge of the Sith novelization.
Rebellion era includes the novelizations of the three original trilogy movies, all of which are pretty good. I can recommend Allegiance and Truce at Bakura, but it’s been a while since I read anything from here.
New Republic era, I could go on and on about. The X-Wing series is a great one if you’re into the inner workings of the Republic and some of the minor characters and such. The Thrawn Trilogy, I must say, contains some of my all-time favourite books. The Jedi Academy Trilogy and the Corellian Trilogy are also good ones. I would recommend going in order of the books here, if you’re willing, because they’re all nice stories and they have plenty of background information. If anyone wants more recommendations from this era, I’ve read every single novel marked in blue on that list. Whoops.
The New Jedi Order era is made up almost entirely of one series, incidentally called the New Jedi Order series. It’s a good one, but if you don’t like major character death or committing to such a long series… maybe don’t. Again, I’ve read way too much from this era for my own good.
Legacy era is made up mostly of the Legacy of the Force and Fate of the Jedi series. They’re good, especially the former, but they can get depressing. Plenty of major character death, others getting their lives ruined, everyone is getting older. It’s very nostalgic and contrasts sharply with the tone of the newer books, both Legends and canon.
Speaking of canon, there are also newer books that aren’t included in the Legends list. Some of the ones in the canon list haven’t come out yet, but the ones that have, I’ve heard good things about. So far I’ve read Dark Disciple and Ahsoka (I can highly recommend Ahsoka, it’s exactly my kind of story). I know others here have read Catalyst, and I’m sure someone’s read the Aftermath series and/or Bloodline, so if you’ve got anything to say about those ones it’d be great.
Uh, yeah, that got long and a bit off-tangent, but I hope it makes the EU a little bit more navigable. I started with all the post-Empire stuff, but I don’t think it makes a huge difference where you start. Also, both those lists are organized by in-Universe dates, so you can probably fit the canon books into the Legends ones. If anyone sees anything I’ve missed, or has any info for anon here, please don’t hesitate!
Good luck!
~ Jacen