Hi,

It kind of depends on whether you are doing this on the iPhone itself, or doing 
it on your Mac/PC in iTunes then moving it over.  If you have Apple Music or 
iTunes Match where the iCloud Music Library is present, then the latter is the 
best, otherwise, we can make something work.  In either case though, this is 
most easily accomplished if the music is properly tagged as having the Genre 
Christmas, Holiday or something common like that.  Also, with respect to the 
random order, simply use the Shuffle All feature and they will be played in a 
random order, no need to have the playlist items in any specific order for them 
to be played in the random order.

On the iPhone itself, I'd go into the Music app, double-tap on Library then 
flick right until you hear Genre.    Double-tap it.  All Genres on the iPhone 
will then be listed.  Just double-tap on the one you want then double-tap on 
the Shuffle All button.  It will just play them in a random order for you.

In iTunes, you could use a similar method as above and simply select the Genre 
you want, move to the table of songs within that Genre, do a Select All and 
create a playlist from that selection using the cmd-shift-n shortcut.  You 
could also do a Find from within the main library of iTunes with the key word 
"Holiday" or "Christmas".  the resulting titles could then be added to a 
playlist by pressing cmd-a to Select All, then use cmd-shift-n to create a 
playlist.  the resulting playlist could be transferred over to the iPhone 
either via the iCloud Music Library or by syncing the specific playlist from 
within iTunes.

I realize that this is not a step by step answer, but I can go into more 
specifics once I know more specifics about your situation.

Later...

Tim Kilburn
Fort McMurray, AB Canada

On Nov 27, 2016, at 19:03, Brian Hansen <[email protected]> wrote:

I’m hoping someone can give me a bit of help here.  I need to create a playlist 
for all of my wife’s Christmas music.  Is there an easy way to get her hundreds 
of songs into the play list, and then have iTunes generate a randomly sorted 
playlist she can use on her iPhone?  Thanks for any and all help.

Blessings,

Brian

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