Is Berlusconi the happiest man alive?

I've just re-read Plato's Republic, while I was in Las Vegas for The Amazing Meeting. I really recommend reading the Republic in Vegas, it's kind of a perfect mash-up: Plato's vision of the city of God amid all the gaudy unreality of the city of sin.
The first time I read the Republic, about six years ago, I very much admired the writing, while being slightly appalled at the authoritarianism of the philosophy: the rule by the intellectual elite, the denial of full political rights to most of the population, the eugenics of deformed children, the resistance to any innovation, the state control of everything from when citizens ate to what music they listened to - all of this I found rather exasperating. It made me want to pull Plato's beard. This time, however, I found myself wondering how much of it Plato really meant. I started to realize (rather belatedly) the layers of irony and playfulness in Plato's writing - he never says what he thinks, but rather sets up a sort of puppet theatre where various characters voice various opinions.
There's this moment in the Republic, which I think must be a joke, where Socrates says actors should not be allowed in the Republic because they play multiple characters. And yet Plato says this through a character. And then one of Plato's puppets tells us that all the world is, in fact, a puppet theatre, and that divine reality exists somewhere beyond it. It reminds me of some of Shakespeare's reality-destabilizing speeches, like 'All the world's a stage'. The whole thing is rather trippy, and playful - it reminds me of post-modernist books like Gravity's Rainbow.
Anyway, there is of course a serious purpose behind the Republic (at least, I think there is). I think one of the points of the book is to answer the question: is the philosopher happier than the tyrant?
The argument, put forward by Thrasymachus right at the beginning of the book, is that morality is a convenient human construct which we obey simply to get on with everyone else and avoid getting arrested - this was an intellectually trendy view-point in Plato's day, as it is today. There's no such thing as good or bad in any transcendent sense, Thrasymachus argues. And if we were powerful enough, we would throw off the conventional inhibitions of morality and satisfy all our desires. We would do whatever we damn well pleased. Socrates tries to prove that this is not so, and concludes that the philosopher is, to be precise, 729 times happier than the tyrant (surely another joke?)
I think this is a really good question to consider, and we shouldn't dismiss it, but should really ponder it. Let me put it this way: is Silvio Berlusconi the happiest man alive?
Berlusconi is not exactly a tyrant, but he has enough power and wealth to pretty much do as he wants in Italy, without much regard for law or popular opinion. He can have as many houses as he wants, in some of the most beautiful places in Italy. He can sleep with the most beautiful women in the world (and he does). He can run his businesses without concern about competition, and his politics with little concern for legal consequences. So in an animal sense, he has a pretty good life, with most of his wishes gratified. I think if a poor, obscure and undersexed philosopher came into his presence and said that he was 729 times happier than him, Berlusconi would laugh at him, and so would everyone else.
From a Darwinian point of view, that's to say, from the point of view of evolutionary psychology, would we not have to say that Berlusconi is in fact the dominant male in Italy, the pack alpha, the fittest in his society? Yes, quite a few people in Italy don't like him, and there's a chance he'll end up in prison. But he's been in power for almost two decades, and I imagine he has had a lot of fun, in terms of animal, sensual pleasure.
We might admit that Berlusconi has had a lot of fun, while still insisting he's had a 'bad' life. To which he might reply: 'So fuggin' what? You can keep your virtue, which is really a poor consolation for people who don't have any power. Gimme a choice between virtue and bunga-bunga, and I choose bunga-bunga. There's no God, no after-life, there's just this life, and I've had an incredible life.' Or we might say to him, 'well, have you really had an incredible life? Didn't your wife leave you? Aren't you actually a rather lonely and frightened man?' To which he might reply: 'No! Fug you! My life has been one long incredible bunga-bunga party!'
And might not a young person, faced with the choice between Berlusconi and that pale, impoverished and undersexed philosopher, also choose bunga-bunga? Or, in other words, faced with the choice between virtue and pleasure, might they not choose pleasure?
Plato tried to show that the virtuous life was also the most pleasant or happiest life. But to do this, he had to bring in stories about the after-life and reincarnation, to show that, while the tyrant may have had a pretty good party here on Earth, in the after-life they'd be condemned in Tartarus. But if we don't believe in the after-life, I wonder how we can argue that Berlusconi isn't having a hell of a time? Readers, please, convince me.
[Photo is by Ricardo Stuckert from WikiCommons.]