The Mythical Man-Month
Frederick Brooks's 1975 book — still the most-cited book on software project failure. Based on IBM OS/360.
Contains Brooks's law, "no silver bullet", second-system effect, the surgical team structure. The 1995 edition added new chapters where Brooks reflects 20 years on. "Nine women can't make a baby in one month" is his analogy. Standard reading in any CS curriculum. Most wonderful aspect: Brooks humbly admits his own OS/360 mistakes.