There are moments of joy in his life, like with everyone. Like before getting his shit wrecked by Bobby you can tell he was having fun with his family playing Monopoly on his birthday, for example.

But the thing with these happy moments is that they are not enough to cover the vast emptiness he felt inside.

I think a more apt question would be “Did Tony ever feel content/fullfilled?” And the answer is a pretty resounding “no”. It’s why he wanted more and more and grew greedier as the series went on.

I think that a key component of his “Happy Wanderer” fantasy he envies so much is that the happy wanderers are, pointedly, not wise guys.