music play

The usual reason for this is that you've accidentally unticked all items in the playlist or the whole library. You can enable checkboxes/tickboxes from Edit > Preferences > General tab > Show: and ctrl-click any empty checkbox to check all items in the current view.

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What happens when you try?

If the same song plays again, turn off the Repeat 1 function by clicking on the icon in the Now Playing window:

and close up...

Alternatively, use the menu; Controls/Repeat/Off

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However, if the issue is that the player stops after each song, then this will be because every other song in the list has been unticked (unchecked). Look in the Songs View:

If the tick boxes are not ticked (checked), it means that iTunes will skip that song. So if everything in the list is not ticked, you can play any of the songs by specifically clicking on it, but once it finishes, the player will stop.

Click the tick-box to turn the tick back on. To turn on many songs in bulk, hold down the CTRL key and click the tick-box. Be aware that if the list has a mix of ticked and unticked, you may need to click twice to get the result you want.

The less common reason is that you are in shuffle play mode, and all tracks are set to skip when shuffling, but you're less likely to arrive in that state by accident.

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