I'd add that it doesn't matter whose story it is, if it isn't essential to the story then you shouldn't devote a whole chapter to it, nor even a scene.
Having Philip say "I used to play in a Big Band, back in the day" is enough to draw a query from Bobby, which then allows you to offer up a whole paragraph of monologue. Keep the story on track or the reader will have expectations that Philip's backstory is somehow essential to the plot.
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