July 28, 1962 -- Mariner I space probe. A bug in the flight software for the Mariner 1 causes the rocket to divert from its intended path on launch.
1982 -- Soviet gas pipeline. Operatives working for the U.S. Central Intelligence Agency allegedly plant a bug in a Canadian computer system purchased to control the trans-Siberian gas pipeline.
1985-1987 -- Therac-25 medical accelerator. A radiation therapy device malfunctions and delivers lethal radiation doses at several medical facilities.
1988 -- Buffer overflow in Berkeley Unix finger daemon. The first internet worm (the so-called Morris Worm) infects between 2,000 and 6,000 computers in less than a day by taking advantage of a buffer overflow.
1988-1996 -- Kerberos Random Number Generator. The authors of the Kerberos security system neglect to properly "seed" the program's random number generator with a truly random seed. As a result, for eight years it is possible to trivially break into any computer that relies on Kerberos for authentication. It is unknown if this bug was ever actually exploited.
January 15, 1990 -- AT&T Network Outage. A bug in a new release of the software that controls AT&T's #4ESS long distance switches causes these mammoth computers to crash when they receive a specific message from one of their neighboring machines -- a message that the neighbors send out when they recover from a crash.
1993 -- Intel Pentium floating point divide. A silicon error causes Intel's highly-promoted Pentium chip to make mistakes when dividing floating-point numbers that occur within a specific range. For example, dividing 4195835.0/3145727.0 yields 1.33374 instead of 1.33382, an error of 0.006 percent. Although the bug affects few users, it becomes a public relations nightmare. With an estimated 3 to 5 million defective chips in circulation, at first Intel only offers to replace Pentium chips for consumers who can prove that they need high accuracy; eventually the company relents and agrees to replace the chips for anyone who complains. The bug ultimately costs Intel $475 million.
1995/1996 -- The Ping of Death. A lack of sanity checks and error handling in the IP fragmentation reassembly code makes it possible to crash a wide variety of operating systems by sending a malformed "ping" packet from anywhere on the internet. Most obviously affected are computers running Windows, which lock up and display the so-called "blue screen of death" when they receive these packets. But the attack also affects many Macintosh and Unix systems as well.
June 4, 1996 -- Ariane 5 Flight 501. Working code for the Ariane 4 rocket is reused in the Ariane 5, but the Ariane 5's faster engines trigger a bug in an arithmetic routine inside the rocket's flight computer. The error is in the code that converts a 64-bit floating-point number to a 16-bit signed integer. The faster engines cause the 64-bit numbers to be larger in the Ariane 5 than in the Ariane 4, triggering an overflow condition that results in the flight computer crashing.
November 2000 -- National Cancer Institute, Panama City. In a series of accidents, therapy planning software created by Multidata Systems International, a U.S. firm, miscalculates the proper dosage of radiation for patients undergoing radiation therapy.
My personal favorite is the Therac-25. What bonehead let that go without knowning that would happen?