I think I have some insight for you. But can you give an example of two of what you mean and how it happened?
I think you may have answered your own question. But I went through a period of time about 6 months ago where I would hear the same 1-2 songs over and over again. Sometimes 10 times a day. It didn't matter what radio station I would tune to, they same 2 kept coming through more often then they should. And they were songs that were not normally in the present popularity rotation on air waves because they were a couple years old. And to my frustration I could not figure out the relevance to either song. And then as the weeks passed on they went away. I think there was a message for me in there somewhere, but I missed it.
I do believe that our spirit guides try to communicate with us in many ways. And those of us that are psychically inclined are better able to notice these communications. I get angel numbers all of the time (repeating numbers that have meaning). I also like you had songs coming up repeatedly for a time. And I've also seen some messages on billboards and signs that caught my attention. I think in your case, your guides may be giving you messages through the songs. It may be something personal for you to understand, or it may be a message for you to help someone else. Although, you seem to have the ability to really get inside people's heads and take on their emotional energy in an overshadowing type of way. I think you are highly tuned and are getting help from your guides to better understand what is going on so that you can help people.
Are you hearing the same song over and over in relation to a particular person, or just in general? I was not sure from what I read above. The message might be for them, if it is related to someone other than you.
If it seems to be a message for you, this is popularly known as an ear worm, and is a part of OCD, though when it occurs by itself, it is considered normal. I have it badly enough now that I am severely sleep deprived that I consider it extremely annoying.
In my case it did not seem connected to someone else, and it took me about 3 weeks of the same two songs playing in my head whenever I was not asleep before I finally figured out what they had in common and were trying to tell me about where I should put my attention in my life. Just as it was with Hop Daddy, both songs were not currently popular. At least I liked them. I have had songs stuck in my head that I did not like.
I agree with Hop Daddy that if this is likely a message from your spirit guides, unless it is paired with other symptoms. For me it really helped to figure out what the 2 songs had in common. I hope you can remember the 2nd one and figure that out, as it might hold a clue.