Trying to download all my music onto iPhone, doesn't work?

Trying to download all my music onto iPhone, doesn't work?
As you can see, the "Nearer My God to Thee" and "Need you right now" songs are on my phone, and I've tried a lot of things to get the "need ro deel loved" songs on my phone as well. I go to my iTunes, purchased, then I think I clicked on "most recent" (even though I bought these songs like 2 years ago?) and then name, download all and then it ends up looking like this. I can't select them so can't listen to them either... Sorry if this is confusing but I hope someone has maybe had the same issue and knows how to fix this? Thanks in advance!!!
Updates:
Sorry has to be "need to feel loved".

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  • I dont want to lead you up a garden path and im not sure. But maybe in itunes you need to go to the list of songs and on the left it will have checkboxes. The checkboxes should be ticked for them to sync properly. If they are not ticked then they won't sync on your iphone.

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  • Does your phone have enough space for the download? That could be an issue.

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