Old head means: An older male gangsta or thug, especially one who is no longer active; an older black man with street cred.. It is informal slang, fine in casual speech but not suited to formal contexts. There is no real cause for parental concern; it is descriptive vocabulary rather than risky behaviour. If your teen uses it, context will usually make the intent clear. A short, curious question about where they heard it is usually all that is needed to know whether to follow up.