A$AP Rocky is a rapper who was influenced heavily by Houston rap in his music even though he is from Harlem. On his first album, LIVE.LOVE.A$AP, he has a bunch of psychedelic, slow, chill songs reminiscent of Houston, one of them being Houston Old Head. What makes Houston Old Head different from the rest of the songs on the album is how introspective it is compared to the rest.
An “old head” in this context is a mentor who is older and wiser than you. Rocky talks about going to Houston to visit his old head so he can get some advice from him. Rocky vents about how he feels like giving up, but he feels like he can’t because if he stops rapping, he will starve. His old head gives him some basic but powerful advice. He basically tells Rocky that he’s just going through the perils of life, and he would experience these things regardless of what he chose to do.
Later in the song, Rocky’s girlfriend calls him and tells him that he should come back to Harlem, stop buying and dealing drugs, and keep rapping because she knows it’s his true passion, and she wants what’s best for him.
I feel like this song embodies the idea of more of the negative feelings surrounding the American Dream. Even though Rocky’s Dream is to become a famous rapper, he’s struggling to keep himself motivated to get there. He goes to someone who he trusts to ask for advice, and all he gets in return is “that’s just life”. Luckily, Rocky did keep rapping and has made an extremely successful career off of it.