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Some people will exchange midi files.
Some people do colaborations so they are actually present in the same location etc. But in most cases it involves production techniques using keyboards sequencers and so on.
If you are clever with track selection you can do one of those mash up type remixes on DJ equipment but to be honest they are a bit cheap n' cheesy. Like for example the 'Let me show you lizard' mashup of Camisra and Mauro Picotto. Although it was probably done on a PC you can do similar things with decks. Turntablists have been doing it for years. There are certain types of applications that will actually do this for you automatically so it's not even clever. It's called beat munjing (Not sure on that spelling) but the software is not cheap.
You mention the chip monk voices. Again to avoid that you need proper pitch adjusting sortware, and again it's not cheap.
If you are going to do the Turntable version there are a couple of things you need to be aware of. Mainly the key of the two tracks/samples you are sticking together. They need to be the same or atleast compatible. You also need good mixing skills so that it doesn't sound bodged as many people get voices and so on out of time and make some really nasty corrections in the middle of it. It's actually better to adjust the track without voices or melodies as this will sound less obvious. Something that's true in all mixing not just mash ups.
All the best
Nem
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https://www.mixcloud.com/Calvin_Karass/
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