A friend of mine asked me to recommend to him a book that would be a great introduction to Gene Wolfe. This particular friend I wouldn't say is a regular reader of science fiction and fantasy books, but he isn't completely alien to them either. In my own opinion, the "Books of The New Sun" are by far Wolfe's best. They're good for many rereads and chock full of everything that makes a story worth loving. However, it didn't seem wise to suggest such a large omnibus, whose pages number around 1500, to a person who didn't regularly immerse himself into the Science Fiction and Fantasy genre. I wanted to suggest something that would show him just how intelligent and imaginative of a writer Wolfe is without scaring him into thinking he'd have to invest a countless number of hours in an Elf-crazed-Tolkienesque sized universe filled with maps and imaginary dead languages. I wanted to suggest something slightly simpler. So I decided on the following three books as good, but not overwhelming, introductions to Gene Wolfe:
"The Fifth Head of Cerberus" Three beautiful novellas set in the future on a colonized (or conquered?) planet. It's been on my re-read list for a while, and I felt it would be the least intimidating to start with because it breaks Wolfe's work up into three pieces that are easier to digest than his more robust novels. It's also filled with beautiful characters and interesting discoveries. It would probably be my first recommendation.
"The Sorcerer's House" One of Wolfe's more current novels and also one of my all time favorites. When I met Gene at MadCon in 2010 I actually had him sign my copy, because I had enjoyed it so much. This book is a series of letters from a man who was recently released from prison, to his brother, concerning a house he inherits and the events that transpire within it. It's definitely a fantasy filled with some fantastical creatures and characters, but for me personally, it seemed to take the normal and mundane pieces of life and polish them up into something remarkable as well. I'd recommend this novel to anyone, and it's an easy read for first time Wolfe readers.
"Free Live Free" This particular book holds a strength in character development that as an amateur writer I could only dream of achieving. It's a mystery with a dash of the fantastic sprinkled throughout it. I will admit it has it's rougher parts, but nothing about it seemed meaningless or poorly executed. If you judge the books you read by the quality of their characters than this is certainly worth your time.
Now these are just my personal recommendations. I've read over 30 of Gene Wolfe's books and there wasn't one that disagreed with me. They were all immensely enjoyable. These three just seemed like the ones I'd recommend the most to people wanting to experience Gene Wolfe for the first time. Feel free to comment with your own suggestions!