According to one website aimed at expatriates living abroad, Singapore is a 'fine city. This is a joke that touches on the cleanliness of the streets as well as the stiff monetary penalties involved in breaking littering and vandalism laws.
The ban on chewing gum is part of these "keeping the streets clean" laws. Chewing gum stuck on sidewalks and in public places was expensive and labor-intensive to remove. More than once, chewing gum stuck to train doors shut down public transportation. The government of Singapore figured that imposing strict penalties would eliminate the problem, and it became illegal to chew, sell, possess, or import chewing gum.
In a country where jaywalking and public displays of affection are also taboo and getting caught with enough drugs means a mandatory death penalty, giving up the gum wasn't the worst thing in the world. Singapore is known for being rather obsessive about keeping up its appearance and having many harsh laws with strictly enforced penalties.
Enter Michael Fay. In 1994, Michael Fay got caught with a group of kids who were vandalizing local property and cars. Despite his being an American teenager living abroad, he was arrested and sentenced to four months in prison and a fine of over $2,000. In addition, he was also sentenced to a caning for being in posession of a highly dangerous substance, ie chewing gum. Being whacked with a cane is no joke - some people who have been caned have gone into shock from the wounds, and many have permanent scars. It's often compared to medieval flogging.
Suddenly, Singapore and all its crazy laws and stiff consequences for breaking them were in the international spotlight. President Bill Clinton got involved in making pleas to Singapore on behalf of Michael Fay, but the Singaporean legal system does not usually back down.
In a country where not flushing a public toilet can lead to arrest, some people thought Michael Fay should be given leniency as an American citizen. Others argued that when you live or travel in a foreign country, you're obligated to respect their laws (even the ones that seem crazy) and accept whatever consequences might come for breaking them.
In academic circles, Michael Fay's caning added fuel to the fire of the cultural relativism debate. Is it okay for one group of people to hold vastly different ideas about right and wrong? Is it correct to interfere with another state's cultural practices when you believe something to be morally reprehensible? While the debate on cultural relativism will likely drag on forever, the Michael Fay case was an example of another country's seemingly crazy laws that will stick in our memories for a long time to come.
In the end, Michael Fay's sentence was carried out, though he was only given four lashes of the cane instead of six. Result? A catastrophic drop in American tourists and billions of dollars worth of trade vanished overnight. Singapore's image as a civilised western-style state was destroyed, literally, at a stroke.