The problem does not lie so much in the difference between
America and Singapore. Rather, this problem is a plague that's
endemic of all rogue regimes run by despots and tyrants.
Think about it : how many dictatorships have actually afforded its
masses the fundamental rights to the freedom of thought, freedom of
expression, freedom from want? Essentially, such values form the
cornerstones upon which any democracy (regardless of how their
Constitutions and governments are structured) flourish. It's hardly
rocket science to work out if such values were preached in
dictatorships and other oppressed regimes, the very act of
exercising such rights are effectively a direct threat to the
interests and existence of those perpetuating such rogue regimes.
The "symptoms" you describe that are endemic of life in such
oppressed regimes are merely the tools and stigma which the despots
would so dearly love to inculcate in its citizenry so as to ensure
social cohesion and harmony could be effortlessly maintained. After
all, in sociological terms, how else could such tyrants possibly
castigate deviants who are out to reveal the truth?
Ultimately, it's not hard to see the repercussions of such policies
in these rogue regimes have a detrimental impact on its citizenry
far beyond political ramifications - is it then any wonder why
citizens schooled in a liberal democracy where rights and freedoms
are no less cherished than "law and order" or "bread and butter"
actually develop a better acumen towards managing their finances,
possessing a certain depth in thought quintessential to success in
life (among a host of other qualities)? 
