I'm not saying Lil Wayne is the greatest, but he's not terrible because he raps about money, and drugs and such. I don't know about these rappers lives, but some of them have actually gone through this stuff.
One rapper I'll never like is Rick Ross. He's a terrible rapper, and isn't even from Miami.
For my list I gotta go with
2) Twista (another "money" rapper but I like his flow)
3) Jay-Z, I never really like this guys singles, but a lot of his songs are really good.
5) Lil Wayne.
Young Jeezy really isn't that bad either. Sometimes people need to stop caring about what they're saying and listen to the music. I listen to rap for the "flow" and the beat. I could careless about diamonds, bitches and weed.