This song is making the statement that drugs should be legal. The older generation enjoys alcohol the same way the younger generation enjoy drugs and since the substances are already in the culture then in the land of the free who is the law to tell you what you can put in your body? In many ways, the song is a call for legalization.
This song is about getting busted for drugs and getting sent to jail. The song came together after the band played a show in Kentucky, where they learned that getting caught with just one joint gets you an automatic month long sentence in jail. They were also talking about a weed dealer they knew in Kentucky who they hadn’t seen in about a month.
There are several drug and alcohol references in this song: “Red Lebanese” and “Black Napalese” are forms of hash, and Newcastle Brown is a kind of beer
Inspiration for the title comes from a Humphrey Bogart/James Cagney movie, where Bogart plays a prisoner who gets sent to a month in solitary confinement or it might have been from the 1956 movie Somebody Up There Likes Me, where Paul Newman is threatened with the a month in solitary confinement
Either way this song will always remind you that if you get caught in Kentucky that’ll get you 30 days in the hole
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