The short version is that if it sounds good, it is good. And your ears will get better at that as you gain experience. As if by magic.
You know, unless you're tone deaf.
If you're using Live, you can also adjust keys in the clip edit view. And if you need to, you can automate it. It won't sound good if you go too far, but it can shift a semitone or two with no problems.
If you want a crash course on music theory,
this is a good reference. There's a
lot of information there, and most of it isn't relevant to you. But, if nothing else, it can give you the terminology to start googling or youtubing for answers.
Mashups are actually somewhat difficult. If you're just putting an a'capella over another beat, that's relatively easy. It just has to not clash, and Live's key adjustment works great for that. Just listen and see what needs to change. If you're mashing up 2 songs with different harmonic content, there's a
lot more to think about in terms of melodies and chord progressions.
Fortunately, a lot of music is written with the same patterns, especially within a genre.
"Every rock song ever" is a simple chord progression of G C D (or I IV V in different keys). It's not actually every song, but it's more true than you'd think. Most classic Blues fits the 12-bar quick change blues riff. In the key of G, it's G C G G C C G G C D G G, with the same basic pattern played in each for 1 measure each. If it's in a different key, you just move the same pattern up or down.
Most successful mashups I've heard seem to start with the producer realizing "hey, these songs are insanely similar." For example...
That's a different progression, but it's kind of crazy how many songs fit that same chord progression. Seriously, watch his left hand. The rhythm changes a bit, and he has to sing some of the songs in pacabel's rhythm instead of the origianls, but...yeah. It'a kind of crazy.
Also, yes, Pachabel's first name was Johan.
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