HT1399: Playing and managing content in iTunesLearn about Playing and managing content in iTunes
Currently Being ModeratedOct 3, 2013 12:16 PM (in response to rjceasar)
Sounds like you need to click the column heading above the numbers so it sorts your playlist by song order, then you should be able to drag them:
Change the order of songs: Drag the songs into the order you want. If you can’t drag a song, click the column heading above the numbers.