1. On October 16, 1859, abolitionist John Brown and 21 other men raided the federal armory in Harpers Ferry, Virginia, which was then part of the state of Virginia. The raid was an attempt to steal weapons and spark a slave uprising, but it ultimately failed and resulted in Brown's execution.
2. In 1916, President Woodrow Wilson signed the Jones-Shafroth Act, which granted U.S. citizenship to residents of Puerto Rico. The act also established a government in Puerto Rico and gave the island more autonomy.
3. October 16, 1962, marks the day when President John F. Kennedy was informed of the discovery of Soviet missile sites in Cuba, which sparked the Cuban Missile Crisis. The crisis lasted for 13 days and was a pivotal moment in the Cold War.
4. On October 16, 2000, Microsoft released Windows ME, the last version of the Windows 9x operating system. The system was criticized for being buggy and unreliable, and it was eventually replaced by Windows XP in 2001.
5. In 2004, the first episode of the medical drama "Grey's Anatomy" premiered on ABC. The show, which is set in Seattle and follows the personal and professional lives of a group of doctors, has been on the air for over 16 seasons and remains popular with audiences.