The longest hiccups lasted nearly 69 years. When Charles Osborne started hiccupping in 1922, he didn’t stop until 1990. Charles Osborne hiccupped non-stop for 68 years. He wasn’t even doing anything to trigger his decades-long hiccup – it just started while he was weighing a hog before slaughter. Initially, he hiccupped 40 times a minute. However, in his later years, it slowed to 20 hiccups per minute. After his long hiccupping episode, he managed to live a hiccup-less life for only a year until he died in 1991. One of the more unfortunate WTF facts.