Some of the ealier books may be off a year (going from memory)

2020:
For We Are Many by by Dennis E. Taylor
We Are Legion (We Are Bob) by by Dennis E. Taylor

2019:
The Making of a Manager by Julie Zhuo (NF)
Thinking in Bets by Annie Duke (NF)

2018:
The Advantage by Patrick Lencioni (NF)
Mindset by Carol Dweck (NF)

2017:
Measure What Matters by John Doerr (NF)
Scaling Up by Verne Hamish (NF)
The Five Dysfunctions of a Team by Patrick Lencioni (NF)

2016:
Rework by Jason Fried and DHH (NF)
Fierce Conversations by Susan Scott (NF)
Radical Candor by Kim Scott (NF)

2015:
High Output Management by Andrew Grove (NF)
Work Rules! by Laszlo Bock (NF, audio)
The Hard Thing About Hard Things by Ben Horowitz (NF, audio)
Drive by Daniel Pink (NF)
Managing Humans by Michael Lopp (NF)

2014:
Second Foundation by Isaac Asimov
Animal Farm by George Orwell
The Princess Bride by William Goldman
Frankenstein by Mary Shelley (audio)
Starship Troopers by Robert Heinlein (audio)
Foundation and Empire by Isaac Asimov
The Eye of the World by Robert Jordan (audio)
Fahrenheit 451 by Ray Bradbury
Ready Player One by Ernest Cline

2013:
American Gods by Neil Gaiman
Foundation by Isaac Asimov
A Dance with Dragons by George R. R. Martin
A Feast for Crows by George R. R. Martin
Mockingjay by Suzanne Collins 
Catching Fire by Suzanne Collins

2012:
Hunger Games by Suzanne Collins

2011:
A Sorm of Swords by George R. R. Martin
A Clash of Kings by George R. R. Martin
A Game of Thrones by George R. R. Martin
The Girl With The Dragon Tattoo by Stieg Larsson
Cloud Atlas by David Mitchell
Anathem by Neil Stephenson 

2010:
Northern Lights by Philip Pullman
The Subtle Knife by Philip Pullman
The Amber Spyglass by Philip Pullman

2009:
Smart and Gets Things Done by Joel Spolsky (NF)
Joel on Software by Joel Spolsky (NF)
Cat's Cradle by Kurt Vonnegut (MP3)

2008:
Jonathan Strange and Mr. Norrell by Susanna Clarke (MP3)
Lamb by Christopher Moore (MP3)

2007:
I am American (And So Can You!) by Stephen Colbert (NF?, MP3)
I am Legend by Richard Matheson (MP3)
Harry Potter and the Deathly Hallows by J.K. Rowling (MP3)
The Golden Compass by Philip Pullman (MP3)
Hard-Boiled Wonderland and the End of the World by Haruki Murakami
You Suck by Christopher Moore (MP3)

2006:
The Areas of My Expertise by John Hodgman (NF?)
The Stupidest Angel by Christopher Moore (MP3)
A Scanner Darkly by Philip K. Dick (MP3)
A Dirty Job by Christopher Moore (MP3)
The Party Cloudy Patriot by Sarah Vowell (NF, MP3)
The Name of the Rose by Umberto Eco (MP3)
Candide by Voltaire (MP3)
Fraud by David Rakoff (NF, MP3)

2005 (commute from SF to SJ, lots of Audiobooks):
Hegemony or Survival by Noam Chomsky (NF, MP3)
The Lion, the Witch, and the Wardrobe by C.S. Lewis (MP3)
Harry Potter and the Half-Blood Prince by J.K. Rowling (MP3)
A Confederacy of Dunces by John Kennedy Toole (MP3)
Pattern Recognition by William Gibson (MP3)
Breakfast of Champions by Kurt Vonnegut (MP3)
Kitchen Confidental by Anthony Bourdain (NF, MP3)
White Noise by Don DeLillo (MP3)
Paradise Lost by John Milton (MP3)
The Picture of Dorian Gray by Oscar Wilde (MP3)
On Intellingence by Jeff Hawkins and Sandra Blakeslee (NF, MP3)
20,000 Leagues Under the Sea by Jules Verne (MP3)
The Fall of the House of Usher & The Pit and the Pendulum by Edgar Allan Poe (MP3)
Flags of Our Fathers by James Bradley with Ron Powers (NF, MP3)
Around the World in 80 Days by Michael Palin (NF, MP3)
A Short History of Nearly Everything by Bill Bryson (NF, MP3)
Stranger in a Strange Land by Robert A. Heinlein (MP3)
How to Talk to a Liberal by Ann Coulter (MP3)
America by John Stweart (NF, MP3)
Red Rabit by Tom Clancy (MP3)
Don Quixote by Miguel de Cervantes (MP3)

2004:
Quicksilver by Neil Stephenson (MP3)
Angels & Demons by Dan Brown (MP3)
The Art of War by Sun Tzu (NF, MP3)
The Davinci Code by Dan Brown (MP3)
I, Robot by Isaac Asimov
Perfectly Legal by David Kay Johnston (NF)

2003:
Harry Potter and the Order of the Phoenix by J.K. Rowling
The Teeth of the Tiger by Tom Clancy (MP3)
A Peace to End All Peace by David Fromkin (NF)
Zodiac by Neil Stephenson
Harry Potter and the Goblet of Fire by J.K. Rowling 
Catch 22 by Joseph Heller (re-read)
The Diamond Age by Neil Stephenson
A Brave New World by Aldous Huxley

2002
Cryptonomicon by Neil Stephenson
How to Make Your Car Handle by Fred Puhn (NF)
The Bell Jar by Sylvia Plath
Harry Potter and the Prisoner of Azkaban by J.K. Rowling 
Closing Time by Joseph Heller
This Side of Paradise by F. Scott Fitzgerald
The Universe in a Nutshell by Stephen Hawking (NF)

2001
Snow Crash by Neil Stephenson
The Sun Also Rises by Ernest Hemingway
Do Andriods Dream of Electric Sheep by Philip K. Dick
Harry Potter and the Chamber of Secrets by J.K. Rowling 
Last Exit to Brooklyn by Hubert Selby
Rainbow Six by Tom Clancy 

2000
The Bear and the Dragon by Tom Clancy
Dune by Frank Herbert
Harry Potter and the Philosopher's Stone by J.K. Rowling 
Catch 22 by Joseph Heller
The Catcher in the Rye by J.D. Salinger
2001 A Space Odyssey by Arthor C. Clark