My guess is he had them all macro’d to keyboard shortcuts and just memorized them. I’m sure a big company like Westwood (N)One had at least halfway decent computer systems optimized for that very thing. Certainly some kind of DAW system too like Pro Tools or Audition where audio could be recorded live then chopped up and made into individual drops or for Best Of shows.
Fun fact: “drops” actually used to be recorded to short looped cassette tapes called “carts.” You had to have each individual audio drop physically recorded to the cart you wanted to play and have tall the carts queued up just right. In the analog world you had to be a lot quicker on your feet! Like everything, as things went digital, drops just became computer files that could be saved to a hard drive and pulled up at the push of a button or mouse click.
You can actually tell from older shows sometimes when Mike or Anderson were still using analog cassette drops because you can occasionally hear a tiny bit of pitch bend from the tape being played (if the engineer hits play while there’s still silence on the tape you won’t hear this but if they’re a little later into the actual signal on it you get that slightly warped sound). I estimated it was around 1999/2000 when W.O. switched from analog to digital audio systems in their studio.
What was never clear to me (or seemingly Adam/Drew as well) was precisely when Anderson was actually recording and when he wasn’t, but I’m guessing it’s just how much he felt like participating in the banter of a show on any given night. If he wanted to get in on it more he probably just had to be following along more closely and actively recording during any calls/bits he thought might be funny.
Anyway, I’ll stop nerding out about audio stuff now, if anyone has anything to add or corrections to anything I said feel free to post em! Glad this site is back up and running, too.