Outdoor Rock Speakers, Wiring Questions

I'm running wire to two rock speakers and will be using one underground PVC electrical conduit to carry two separate 2 conductor cables.  The conduit run will leave the crawlspace of the home with an LB, down to a sweep fitting underground, then straight to the first speaker and coming up with another sweep into the cabinet of the first speaker.  My question is, can this conduit penetrate the bottom of the rock cabinet?  Or, should it come up out of the ground into a watertight JB?  I was thinking of using the first speaker's cabinet as a JB, which would take the conduit down to another sweep, then straight to the second speaker and up again with another sweep into the speaker cabinet.
The second speaker is about 20 feet away.

A Link to the speakers and pics would help answer that I think.
Note, conduit is great and good for you doing it. Some folks just direct bury. That said, a direct-burial-rated wire I’ve seen as often recommended (technically required?) since your conduit may not (will not) remain watertight. Even if it doesn’t get direct rain and ground water you will get condensation that has nowhere to go. Fortunately you can always pull a new wire through your conduit but best to use direct burial wire if you haven’t already bought a big spool of other...


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