100 Books
See allHow to Win Friends and Influence People is really showing it's age. It's full of anecdotal stories involving horses-drawn carts and the American civil war, which are really hard to relate to in this day and age.
The main points of the book mostly boil down to do unto others, don't antagonize anyone and be genuinely nice to people.
Good advice, but the book didn't need to be this long to get those points across.