I believe I have the latest version of iTunes (I could be wrong). I just hit the play arrow up by the name of the playlist and it plays the entire playlist. You don't need to click on an individual song.

I don't like iTunes. I don't know if I have the latest version because I don't know how to use the one I have. My DIL and I have a running argument about it. I think it's complicated, she insists it's easy. Maybe for her it is, but not for me.

The most recent version of iTunes is 12.4.3.1 -- and you no longer see a list of the names of your playlists. It's quite frustrating.

But, if you know that a particular song is in the playlist that you want to play, and you're on a Windows machine you can simply right-click on the name of the song, then click on Show in Playlist. [more text after each picture]

The playlists that the song is in will be displayed in a "flyout" and all you need to do is click on the name of the playlist. That playlist will then be displayed. In the above photo, the song is in my Favorites playlist.

Once your playlist is displayed, you can choose whether or not you want to play the songs in order, or if you want them shuffled. If the shuffle icon is blue, then it is "on" or "active." Click on it to turn off the shuffle. If it's not blue and you want to shuffle, click on the icon and it will turn blue.

If you want to edit the playlist, simply click on "Edit Playlist" and you can add/delete songs.

I, too, am unhappy with many of the changes to iTunes, but Apple seems to not care what people like or are used to, so we're stuck with what we've got.

I have more than one iTunes library on my desktop pc -- one is for my iPod Nano (16GB) which stays in my car, and one for my iPod Touch (128GB). Obviously, I can't put all of my music on the iPod Nano because it doesn't have the capacity, so rather than checking and unchecking songs to sync it, it's easier to have a separate library.

I also hate, hate, hate, that iTunes can't manage to get the artwork for all of the albums, but out of the 320 albums that I currently have in my iTunes, only one doesn't have artwork. It's easy to add.

I moved from iTunes to Amazon Music (free with Prime). It's much easier to sync it to every device.

My computer had me update my iTunes, and when it was done I came here and found this thread. I rarely use iTunes for my music. I just don't like listening to music on my computer. I use iTunes to download the digital copies of the dvd's that I buy. Any music I buy off iTunes goes on to a flash drive and I listen to it in my vehicle.

Thanks for all the comments. I really don't know why they do updates that aren't helpful and "better".

Here's another question: How do you listen to a flash drive in your car? My car is 10 years old, so I may not have the needed plug in....???

I have an 'after market' stereo system in my car with a usb plug so I can just plug in a flash drive and listen to it. Most new cars also have them already built into their stereo.