To add to what’s already been said, as to what they are listening for, with EDM like house and trance, the music is matched by way of the kick drum. So by listening closely they can determine if one track is too fast or too slow and adjust pitch or tempo accordingly. For things like breakbeats and drum and bass, the music is matched on the snare, but the idea is the same.
Everyone answered your question already but they used to sell only one side. https://i.pinimg.com/originals/90/84/96/90849653e9d6163bb8a8fd6a090d6997.jpg
It is kind of a pain to put the headphones on and off and then have to adjust one side of the headphones, so they came up with these one speaker hand held headphones. The people that I saw use these were guys that had residencies at clubs, so they had all the sound dialed in, and they would play for 3 or 4 hours a night.
When I was a dj, it was very hard to hear your headphones when playing on a loud system (club system). So I would wear both sides on my ears and maybe just take one side off just a tad so i can still hear the club speakers.
but to reiterate what everyone is saying, you are basically listening to two songs at once.
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