What tip or practices can you suggest for when creating a medley?
Mike, I figure that making up a melody is like making up an original tune except that you are outright stealing everything from somewhere else. Even if you are doing a medley of your own tunes.
With that in mind I think it is good to figure out why are you making up a medley. Sometimes it is plain and simple, like doing a Beatles medley. If you are doing a medley around an idea or a theme, continually reminding yourself what your goals are as you select the tunes can help you to stay focused and end up with a pleasing outcome.
Being a singing kind of guy like you are, choosing the key for each segment of your medley so you can sing and play comfortably is essential. So if your chosen tunes and the keys you are good with are not all the same key, then you get to play with making the transitions between keys (modulation) and how to stick in a little turn around section, that turns you around to the next target key, and sounds like something that you meant to play. Here is where sequencing the tunes for your medley gets more interesting. If you are trying to tell some kind of a linear story line with your medley, then your modulation may take a bit more imagination, if your story causes you to do something tricky to make it sound like you meant for it to.
Then you have time. If your tunes are not all at the same tempo then you have to figure the time transition into your modulating thinking. Back to your overall goal...if there is a crescendo, or any dynamic pattern to your masterpiece this needs to go into your thinking as well. 4/4, 3/4 it's all good.
Sometimes if I am working at making up a medley and I get stuck the answer that I need only comes to me in some kind of day dreaming process. Like our very first monthly challenge, when Black Coffee Blues put out doing a John Prine tribute. Choosing a few Prine tunes and herding them into some kind of a story like order, that was a process for me, for sure. But when I had a few tunes stitched together it was OK but I felt something was missing and was stuck for ideas. I just let it rattle around in my head for a while and before you know it that old George Jones tune "Who's gonna fill their shoes" came out of the shadows of my mind. That made the closing segment for the medley that I was looking for. It gave my little story, and the tune some resolution I was wanting. It kinda takes the listener through some Prine hits, moving closer to his end with "Oh what a feeling, when my soul went through that ceiling" and ending with "filling their shoes" Corny as hell, but I do corny, I talked my way through my transitions, cheating. If you want to torture yourself here is a link to that medley from April of 2021 I believe.
https://www.dropbox.com/s/lsntg1rrwf032mn/JP BGU Medley 22.mp3?dl=0
Sorry for running on, you can tell I kinda like the medley concept. It will be fun to hear what you come up with someday.