It looks like he has been working on it, albeit years ago: [url]http://www.ventismedia.com/mantis/view.php?id=6689[/url] and needs something additional in order to make it happen.

From the addon thread:
[quote="ZvezdanD"][quote="chimpanzeethat"]Hello,

Many thanks, ZvezdanD. This extension works almost perfectly! The only thing I notice is that there is that before a cued song plays, I hear a second or so of another song from the Now Playing list which kind of interrupts what i'd like to be seamless playback.. This is a minor quibble but just wondering if this 'bug' is unique to my setup?

Thanks again![/quote]
That problem is already reported in this thread and it is hard to resolve because of MM lack in its programing interface. I already reported that to MM developers, but they don't care about it:
http://www.ventismedia.com/mantis/view.php?id=6689[/quote]

Just ask ZvezdanD to modify its script to disable crossfading While there is tracks in QUEUE and it should work much better.

Thanks Peke, the ZvezdanD script works pretty well. It doesn't really work with the crossfading. The next song starts to crossfade in and then it jumps to the next queued track via the script. Still works better than iTunes though. If you come across anything even better please let me know!

Anyway I added http://www.ventismedia.com/mantis/view.php?id=13111 so that Randomize list is easier to access

As you noted solution for you is to Use now playing command to randomize list and then you can use Play Next to control it.

For others if control is not seen Right click on Now playing -> View -> Show playing controls then use Edit -> Randomize list.

You can move that Toolbar off now playing to MMW Main toolbar.

Personally, "Up Next" do not have point if you know what next song will be next.

You can always use ZvezdanD script to Queue Next track http://www.mediamonkey.com/forum/viewtopic.php?f=2&t=49575

That's the only method available.

So I switched to MM a couple months ago when I got fed up with iTunes and it's been pretty smooth sailing since the change. The only thing I miss is being able to use "up next" when shuffling the entire library. Currently, if I turn on shuffle in MM and then right click a song in MM and select "play next" it is the next item in the queue. But then MM shuffles and picks another random song instead of choosing the song I clicked "play next" on. Is there anyway to change this behavior?

I am aware of right clicking on the Now Playing playlist and choosing "randomize list" but I am not a fan of this method.

Thanks in advance!