The video evidence for this important HIStorical question is distinctly ambiguous:
Though the underlying commie music therein is certainly better than Jackson's execrable "Stranger in Moscow" from that period. Furthering the confusion, Jackson in 1996 erected a 35-foot statue of himself in Prague (pictured below) in the exact same spot that once housed the world's largest statue of Stalin himself.
R.J. Eskow "won't claim that Michael Jackson overthrew Albanian Communism," but avers that pop music "didn't hurt." Radio Free Europe, in a truly weird piece of reporting, gives us these tantalizing morsels:
It has been reported that even though Russian President Dmitry Medvedev favorite rock act is Deep Purple, he's had a weak spot for Michael Jackson ever since his early student years. [...]
For reasons that were never fully understood, Jackson received an unofficial blessing from communist censors, who allowed "Thriller" to be licensed and issued as a vinyl record by the Soviet recording company Melodia in 1985. [...]
Jackson's popularity in Eastern Europe in the late 1980s was matched only by that of supergroup ABBA from Sweden. His stunning video clips and original dance moves inspired a generation of performers in the former communist bloc. His live concert in Moscow in 1993 sparked near-hysteria among scores of Russians hungry for a taste of Western culture.
Ilya Shapiro reminds us that:
Michael Jackson's death allows us to remember that such phenomenal career achievements can only be possible in an economic system that rewards and harnesses talent.
The King of Pop's creativity allowed him and his family to make hundreds of millions of dollars, yes, but it also created thousands of jobs in the music and marketing industries and brought joy to fans around the world. Whatever his personal eccentricities — perhaps, in part, as a result of them — Jackson represents a capitalist success story.
No central planner could have invented him, and no government bureaucracy could have transformed pop music in the way he did.
Tell it to Karel Gott, comrade!
As a confirmed backer of the Dallas-overthrew-Communism school of interpretation, I remain unconvinced. However, for those genuinely interested in exploring the intersection of Western pop culture and non-Western liberation, I heartily recommend reading Michael Moynihan on Red Elvis, and Charles Paul Freund's classic "In Praise of Vulgarity."