Ok, I thought that was a button to take you to the Now Playing screen. Thanks.

Yes, on the right image it is left of the search icon.

Here are two images. Is that button on there and I'm not seeing it? The now playing list and the list of files look pretty similar at the top.

It should be shown anytime you're viewing a list of files, except for the Now Playing list.

I don't have that. On the top right of the screen is the 3-dot settings button. Just to the left of that is the search icon.

You can use the Randomize Play button (top right of screen) to add files in a randomized fashion to the Now Playing. Then you can move files around as you see fit.

Our group used to listen to music via Winamp on a laptop. We switched to a phone app, but it's lacking what we need.

We have a list of a couple hundred tunes in our playlist. What we used to do with Winamp was to randomize the playlist and start it up. Sooner or later, someone would decide that they'd like to do a little DJ-ing, and they'd be able to modify the playlist and move their favorite songs so that they're played next, without otherwise disrupting the current playlist.

Is something like this possible with MediaMonkey? Take an existing playlist and randomize it, but we'd be able to see the randomized list and edit it.