Q: I’m making a playlist to be played at a wedding. Is there a way to order the songs in the playlist other than sorting on specific fields like Song Name, Artist Name, etc. I want to control the order of the songs.

– Anonymous
A: Certainly. As you’ve noted, you can sort on specific fields, but you can also change the playlist order manually. To do this, first simply click on the blank column at the very left-hand side of the columns list to return the playlist to its “natural” sort order:

By default, this sorts the tracks in the order in which they were added to the playlist, but once you are in this mode, you can simply select a track, and just drag it up and down within the playlist to change it’s position. Whichever changes you make to the order of tracks will become the new natural sort order, and you can always return to this sort order simply by clicking on the blank column heading again.
Note that you also need to ensure that you do not have “Shuffle” enabled within iTunes. You can confirm this by looking at the “Shuffle” button in the bottom-left corner of the iTunes window, or looking at the “Shuffle” menu option under the Controls menu (a checkmark will appear beside the menu option is the current playlist is set to shuffle).
Further, if you want to start with a different sort order, or shuffle up the playlist and modify it from there, you can sort your playlist by a specific column heading such as “Artist” or “Last Played” or simply enable “Shuffle” and then copy that order back to the default “natural” sort order by right-clicking on the playlist and choosing Copy to Play Order:
This will make the selected sort order the new default arrangement, and you can then click on the left-hand blank column heading again to manually adjust the track order from there. This can be a good way to start with a preferred sort order, or to permanently shuffle up the playlist sort order. Either way, the displayed order becomes stored as the default manual sort.
To ensure that the tracks are transferred to your iPod, iPhone or Apple TV in this order, make sure you leave the left-hand column selected.