Learn Japanese with Anime - You Can't Pay Back What You Owe With Money (JoJo’s Bizarre Adventure)

Analysis

てめー正(しょう)真(しん)正(しょう)銘(めい)の史(し)上(じょう)最(さい)低(てい)な男(おとこ)だぜ

てめー (pronoun) is a very insulting way to say “you”. It can also be written like this: て(て)め(め)え(え).

正(しょう)真(しん)正(しょう)銘(めい)の (noun + particle) means “genuine” or “authentic”.

史(し)上(じょう) (noun) means “in history”.

最(さい)低(てい) (na-adjective) means “lowest” or “worst”.

When a na-adjective modifies a noun, な is attached to the adjective.

男(おとこ) (noun) means “man”.

だ (auxiliary verb) is attached to a noun or na-adjective to affirm the statement.

ぜ (particle) is used at the end of a sentence to give a rough, casual tone, often used in male speech. It draws attention to the statement in a confident or cool way, similar to adding “hey” in English. It’s often heard in anime but rarely used in everyday conversation, as it sounds old-fashioned.

So, てめー正(しょう)真(しん)正(しょう)銘(めい)の史(し)上(じょう)最(さい)低(てい)な男(おとこ)だぜ means “You are genuinely the worst man in history”. In the anime, it translates to “You truly are the lowest scum in history. 

てめーのつ(つ)け(け)は金(かね)では払(はら)えねー(えねー)ぜ

てめー (pronoun) with the possessive particle の means “your”.

つ(つ)け(け) (noun) means “debt” or “what you owe”.

NOTE
つけ originates from the concept of a tab or an unpaid bill that has been charged and must eventually be paid. In this context, it refers to all the harm or consequences that he has caused over time. So, after he pays the price with his life, Jotaro kindly leaves him a receipt.

は (particle) marks the topic of the sentence.

金(かね) (noun) means “money”.

で (particle) indicates means or method, so 金(かね)で means “with money”.

払(はら)えねー (verb) is the contracted form of 払(はら)え(え)な(な)い(い), meaning “can’t pay”.

The は particle here indicates contrast. It’s used with a negative outcome to show that the method—in this case, money—is ineffective or inappropriate, implying that another method might be possible.

ぜ (particle), again, draws attention to the statement with a rough, casual tone, often used in male speech.

So, て(て)め(め)ー(ー)のつ(つ)け(け)は金(かね)では払(はら)えねーぜ means “You can’t pay your debt with money”. In the anime, it translates to “You can’t pay back what you owe with money”.