I'm currently mid Magical Songs quest, got to Rancher Bill and had Timmy as an ally.

 

Normally this puts into a cutscene and Timmy gets stuck stuttering and you can press a button to continue. However, no button is appearing and it just gets stuck on an eternal loop, no button will get me out. Also happened several different times I've loaded the game, this isn't just a one off.

 

Please aid.

You don't actually need to skip it. I did the exact same thing today, just let it play out. It's only like 30 seconds of painfully annoying stuttering. Then again, I was also hitting every damned button on my keyboard at the time. Try just holding down space bar anyways, or whatever your platform has you hit.