The Night Angel Trilogy
The Night Angel trilogy tells the tale of Azoth, a young orphan who barely gets by from day to day as a member of the Black Dragon thieves guild. Azoth and his friends must find a way to steal enough coin each day to pay their dues to the guild enforcer, Rat, and still have some money left over for food. One night Azoth stumbles upon Durzo Blint, the best assassin in the city, as he flees the scene of a just completed job. Street smart and a good judge of character, Azoth asks to apprentice under Durzo but he is instantly rejected by the master assassin. When Azoth's best friend is beaten and raped by Rat, he becomes more determined to apprentice under Durzo so that he can learn to stick up for himself and his friends. Azoth encounters Durzo a second time and threatens to kill him if he won't take Azoth on as an apprentice. Durzo sees something in the boy and agrees to take him on only if he kills Rat by himself before the end of the week.
This shows Azoth right away what his life will be like if he chooses to go down this path. Azoth is not sure that he can accomplish his assignment but when another of his friends is abused by Rat he knows that he must find a way. Azoth sees that he will have to leave behind his life and his friends if he wants to enter Durzo's world of shadows and intrigue and that is a very high price to pay for him. However, he doesn't want his friends to remain victims so he finds a way to kill Rat and delivers his ear to Durzo, thus beginning an entirely new existence for himself.
Almost everything is more than it seems to be and the story gets bigger and bigger as the trilogy goes on. I particularly like the way Brent Weeks is able to shed more light on events from earlier books as the series progresses. I often found myself thinking back on prior events as I learned something new about the characters or the reasons behind their actions. There are multiple magic systems that exist in this world and as the scope of the tale increases more about how they work becomes evident. Overall it is an entertaining take on a dark profession and has a completely different feel to it than the Farseer Trilogy which is also about a young apprentice assassin and narrated in audio form by Paul Boehmer. Paul does a decent job on both series and I now associate his voice with stories about young assassins. :)
The Way of Shadows, The Shadow's Edge, and Beyond the Shadows make up the main trilogy and there is also a short story prequel, Perfect Shadow, that is entirely optional.