Have you heard the song "Worst Behavior"? He seemed insecure and tried to propagate the image that he had it tough. Even in the music video he's trying to communicate that. That's where people try to make fun of Drake is when he's making songs like that or talking about cooking cocaine or whatever and it reeks of trying too hard.
There's nothing wrong with what Drake was doing, when he was making sappy songs or braggadocios songs about how much money he makes or whatever. And people will make fun of him for that. Nothing wrong, its just people will make fun of it. People make fun of Kendrick's nasally voice, etc.
He's currently the most popular commercial rapper right now. Not a particular favorite of mine, but if you like him, cool. I just can't get into his stuff.