Tales from the Mos Eisley Cantina

Tales from the Mos Eisley Cantina by various authors
A collection of short stories, each focusing on one of the characters from the famous bar scene in the original Star Wars movie!

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This is a classic era book from the Legends timeline. It will likely be contradicted by newer books (if so, just think of it as an alternate universe).

(Interested in a New Canon take on the background characters of Star Wars: A New Hope? Check out Star Wars: From a Certain Point of View.)

Tales of the Bounty Hunters

Tales of the Bounty Hunters by various authors
This book is a collection of five (not-so-short) short stories about the bounty hunters seen in The Empire Strikes Back: Boba Fett, Bossk, Dengar, IG-88, Zuckuss, and 4-LOM. It's a varied and interesting look inside the minds of these characters whose loyalty is neither to the Empire or to the Rebel Alliance.

The book's "Tale of Boba Fett" was written before the bounty hunter's childhood was revealed in Attack of the Clones, so there are some contradictions - however, many fans actually preferred this book's take on Boba Fett over the newer backstory from the movies.

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This is a classic era book from the Legends timeline. It will likely be contradicted by newer books (if so, just think of it as an alternate universe).

Tales from Jabba's Palace

Tales from Jabba's Palace by various authors
The palace of Jabba the Hutt on Tatooine comes to vivid life in all its depravity in this collection of short stories tying in to Return of the Jedi. From the band and the dancers, to the guards and the rancor keeper, to the many others hiding in the shadows, this fun and diverse volume takes readers into the lives of the palace's denizens one by one. It's also memorable for a bizarre story of Boba Fett's experience rotting away inside the belly of the sarlacc.

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This is a classic era book from the Legends timeline. It will likely be contradicted by newer books (if so, think of it as an alternate universe). 

The Jedi Academy Trilogy

 
The Jedi Academy Trilogy by Kevin J. Anderson
Though fan opinions vary on its quality, the Jedi Academy Trilogy plays a key role in the timeline of Legends novels set after Return of the Jedi. The series follows Luke Skywalker's mission to rebuild the Jedi Order by searching out Force-sensitive candidates and establishing a new Jedi Academy on Yavin IV. All does not go well at first, with a powerful Imperial superweapon emerging from hiding even as the spirit of an ancient Sith Lord works to corrupt the new generation of Jedi apprentices.

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Book 1: Jedi Search
Book 2: Dark Apprentice
Book 3: Champions of the Force

This is a post-Return of the Jedi series from the Legends timeline. Think of it as an alternate universe from The Force Awakens and newer books.

Darksaber

Darksaber by Kevin J. Anderson
In this follow-up novel to the Jedi Academy Trilogy and Children of the Jedi, Luke Skywalker and his lover Callista set out on a journey of Force discovery, even as an evil Hutt crime lord builds a superweapon inspired by the Death Star. Meanwhile, Admiral Daala consolidates her power over the remnants of the Empire, preparing to strike back at the New Republic and Luke's recently-formed Jedi Academy. Remembered by some fans as one of the worst Star Wars novels, despite being a great financial success.

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This is a post-Return of the Jedi novel from the Legends timeline. Think of it as an alternate universe from The Force Awakens and newer books.