No, no similarity at all,
First of all, Stalin openly take on communism and declared that
he will dictate the people of russian. Tho the Russian
gain and suffered, they understand it, at least Stalin is
true to himself and the russian peoples.
For LKY, he openly said he take on democratic but ruled
singapore like a dynasty, and yet he refused to admit that he
dictates Singaporean way of living. LKY is not true to himself, and
in a way, he makes Singaporeans confuse in his way of ruling,
twisting and turning with policies to make way for more power and
funds from the citizens. And if you ask me why like this, i would
say, it is his skill, his ability and his competency to make
Singaporeans like what it is today, stupid or clever
singaporeans is up to you to imagine. For i know, he rules
with a velvet glove fitting a dirty hand.