Little boxes next to songs and why won't one single song sync?

Somehow when I was messing with iTunes I unchecked every one of the little boxes somehow and I don't know how to get them all checked again?
also I have one song that won't sync and I'm not sure why, it plays fine on my computer but it won't sync to my iPod?

To get them all checked again, select all tracks in library, right click then select the 'check selection' option from context menu popup.
iTunes can handle some file types and formats the iPod cannot. What type of file is it giving problem?

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