Songs purchased on iPhone will not play on Laptop

I have 6 songs that I have purchased on iTunes on my iPhone that don't play on my laptop, instead it just skips on to the next song. I have tried everything I can think of, the files are all in the right location etc. The songs play on my iPhone but I have to download the songs via the iTunes app and going in to Purchases. I don't think they were all purchased in one transaction but are all from roughly the same month. One song in particular is asking for authorization every-time I try to play it and will not play on either laptop of iPhone. Is anyone else having any similar issues?