Cuba can arguably be called democratic by now, though in a very different form than capitalist democracies. EU media is often apprehensive about the whole issue but acknowledges change, while in the US it's the same old talking points up to "Batista did nothing wrong", depending on where you look. It's a bit further ahead in that aspect than Vietnam, which the US has much better relations with.

Russia tends to get completely misunderstood by everyone but its neighbours: Moscow's rule has been based on conquering and oppressing neighbouring regions ever since the Mongols left. It provides them access to раздолье, meaning both expanse and liberty, a word with right-out mythical meaning to the Russian soul, though maybe Americans might actually understand. There's a wide-spread notion among Russians, looking outside, that they want to be a "normal" country, but what that would entail completely eludes everyone, including the opposition.

Because, well, everyone is dozing, not just the depoliticised masses. Quoth Pushkin:

Whatever heavy load it carries,
The wagon's light on steppe and street.
Grey Time, the coachman, never wearies
And never leaves the driver's seat.

At dawn we jump inside the wagon,
Quite happy for our necks to break.
Scorning all soft delight and languor,
We yell "Get going, for fuck's sake!"

By noon we've lost that daring folly,
Being jerked around. We're wagon-sick
Afraid of every hill and gully,
And yell "Slow down, you lunatic!"

But on we rush round every bend.
We're used to it, come evening's yawn.
Heading to night, to journey's end,
We doze. Time drives the horses on.

...quite a lot of soul-searching will be needed for Russia to get its shit together and install a GPS on that cart of theirs. Luckily they messed with the wrong people: Ukrainians, due to cultural closeness, are about the only people capable of cutting off Russia's balls cleanly and thus throw the country into a proper existential crisis instead of trying to find, again, glory in old patterns. There's nothing wrong with Russia attaining glory -- just not like that. It worked out for them in the 1500s conquering what we now call Russia, but the time of imperialism is definitely over. Which is btw why Europe is so "unexpectedly" hawkish: The EU is a decidedly anti-imperial project, "let's band together, united in diversity, so that no empire has a chance to challenge us". Russia's behaviour is an affront to all of that and cannot be permitted to stand.

As far the US is concerned it's good ole cold war memories, they like fucking over Russia because it's the USSR. I mean it would be kinda rich, the US criticising another country for being imperialist...

The Revolutions podcast had a good series on the Russian revolution if that's a format you're into. It includes the birth of Tankies as a name and phenomenon.