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When translating into Latin or writing in Latin, is there a hierarchy between Cicero's writings? For example, if one construction is used in one of his letters and another in one of his speeches, can I arbitrarily choose one or the other as the best Latin?

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When stylists claim to use Cicero as a model, they are chiefly talking about his orations, and his orations are what he is originally known for. Long before he penned philosophy, he was lauded as an excellent orator, to whom only Caesar could compare. (So how unlucky are we that Caesar's orations are lost!)

This reputation stayed with Cicero throughout his life and long afterward. When Antony had Cicero murdered, his wife Fulvia, so Cassius Dio reports, placed a pin in his tongue as revenge for the damage his orations (thinking probably of the Philippics) did to them. Later, when Quintilian is lauding the greatest stylists of Latin and Greek, he compares Cicero and Demosthenes. Demosthenes, of course, is also famous chiefly for his orations (and interestingly his most famous work is probably his Philippics, which, more appropriately named, was written against Philip II, father of Alexander the Great).

Cicero's philosophy probably comes second. Since they're written in dialogue form, Cicero does use some rhetorical devices in them, but they are generally not as well-regarded stylistically as the orations. Not necessarily for the lack of language, per se, but the orations are where Cicero fully recognized his talents and (with some probably polishing after the fact) was able to show those talents off to a wider audience. Meanwhile, the philosophy was largely introspective work, so while it is seen as "good Latin", it's just not what people usually are referring to when they talk about his rhetorical and stylistic prowess. Certainly of course you can find excellent examples therein and many grammars will freely quote from them, so don't neglect them if you want to model your own Latin off him.

The letters are generally not seen as excellent examples of Cicero's style. For one, they were not consciously written for publication. We only have them because they were posthumously publishes, and their importance is more in documenting his life and interactions and the decline of the Roman republic. They most certainly were read by later authors, though, and influenced them. Pliny perhaps had Cicero's letters in mind when he deliberately published his own. But for incongruities between Cicero's speeches and letters, the former are preferred as what Cicero himself saw (and was tested in courts and in publications) as good style.

Finally, avoid his poetry. It was a joke even in antiquity. Some scholars have tried to find positive merits in them, and certainly it can be done, but no one really sees them as excellent exempla to emulate.

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  • Cicero’s letters were extremely influential in the Renaissance, precisely because they modeled an alternative to his grand rhetoric. Petrarch imitated them in his own Ad Familiares, and from there it became a matter of course for influential humanists to curate collections of correspondence. Feb 19, 2023 at 19:27
  • @Kingshorsey No doubt they were influential, and I hinted at their importance when I mentioned Pliny above, who copied Cicero (though less in style than in purpose) over a millennium before Petrarch. Their style is usually not what is meant though by rhetoricians and stylists when they exalt (or denigrate!) Cicero's Latinity (thus my phrasing: "not seen as...Cicero's style"). But yours is a point well made.
    – cmw
    Feb 19, 2023 at 20:46
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Some of Cicero's writings are great examples of Latin prose, but not all are. There are no strict rules about which of Cicero's works are the best to use as examples. It depends on what you're writing and what style you want. If you're writing something personal or casual, Cicero's letters might be more helpful, but if you want to write something more formal or persuasive, his speeches would be a better choice.

You also need to pick the right grammatical construction for the style and context of your writing. You can't just pick a construction from one of Cicero's works and use it without considering if it fits your writing.

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