Mama Smurf said:Jack Black has a LOT of money, is famous, very funny and hardly unattractive. Hardly comparable to some ugly, fat guy with a decent paying job but nothing special who's not famous, and is no more funny than the average person.
You're focused on the wrong type of girl. Even if Jack Black was broke... he'd still get pussy. You said it: He's funny. He's got wit and can make people laugh. Women like that. It show's he's got charisma.
Let's be realistic... Nobody can get every single person they want. However, if you've got game and attitude, the women will want you.