I highly doubt Drake's a HA member. Could he have put some HA members on his payroll to boost his gangster cred? I'd say that's more likely.
As we all know, Drake is the furthest thing from a tough guy. He's an industry plant who rose to fame as a child actor in Degrassi - The Next Generation. I wouldn't say his upbringing was entirely privileged - as a child he was raised by a single mother in a more working class neighborhood and his father did do jail time on some drug related charges - but he never ran with the rough crowd either.