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Will a 5.9 Cummins engine bolt up in 2008 Dodge Ram 3500?

No, a 5.9 Cummins from a different year won't directly bolt into a 2008 Dodge Ram 3500 without significant modifications. While both are Cummins 5.9L engines, there were substantial changes made to the engine and its mounting points over the production years. The 2008 trucks used a 6.7L Cummins, and even if you found a late-model 5.9L that *looked* similar, the engine mounts, accessories, and even the bellhousing (connecting the engine to the transmission) would be different and incompatible. You'd be looking at a very extensive swap, requiring custom fabrication and potentially significant engineering expertise.