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Sometimes it's fairly easy to tell when David is writing about a particular event such as

לדוד בשנותו את טעמו לפני אבימלך

At other times it's less obvious, but you get a 'lightbulb moment' when someone points it out, e.g. Malbim says that Psalm 30 is about David Hamelech's teshuva being accepted after the sin with Batsheva. Are there any commentaries on tehillim, or on Shmuel for that matter which discuss chapters of tehillim in light of the events that inspired them?

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I don't know of a commentary that exclusively does that, but as you've noted, sometimes the traditional commentators will show the connections. (It should also be noted that many perakim were not written by David.) –  Shmuel May 11 at 22:37
    
I would be surprised if there were anyone who did that exclusively but I was wondering if there was someone who did that in such a way that it covered a large portion of David's life. –  Yitzchak May 12 at 20:37

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Artscroll interlinear Tehillim will cover most of it either in a short preface to each chapter or in the notes on bottom.

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