pcrawford said:
I was discussing with a co-worker if you could actually hear yourself yelling if you were free-falling at super sonic speeds.
You'd still be able to hear the sound waves that travel internally from your vocal chords to you inner ear.
A better example would be two people falling. If falling side by side they couldn't hear each other. If one person was above the other, then you'd have the same drafting (just like Nascar) situation, and the air speed relative to the higher person would be sub-sonic if the higher person was close enough. Also because of the draft, the higher person would fall onto the lower person if in the lower person's draft. Another draft effect would be the fact that both persons would speed up as the higher person closed in on the lower person because the higher person would occupy the "void" left above the lower person reducing the pressure decrease and drag on the lower person. This is why two cars in line at a high speed oval track at Nascar are faster than one car, and why 3 are faster than 2.
Mythbusters did an experiment to see if two skydivers could hear each other at normal free fall speed (120mph); and they couldn't because of the very loud wind noise. Foam or similar ear plugs to filter out wind noise probably would have worked, but this was to bust the myths in the movie "Point Break" where ear plugs weren't used.
Getting back to your original question, sound can't travel forward (or any direction) faster than the speed of sound relative to the speed of the air near the objects in question. The draft or shockwave cone affects affect the speed of the air near the objects, so in this case it depends if the relative air speed from the sensing (hearing) point to the target object is sub-sonic. In the case of the two jets, it would depend if the trailing jets engine noise could travel to the leading jets fuselage and cause enough vibration in the fuselage for the lead pilot to hear it. For a simpler example, everyone inside a Concorde traveling at Mach 2 will hear each other just fine.
Regarding super-sonic free fall, it's only been done on purpose once, but there will be another attempt to break the old record later this year:
http://en.wikipedia.org/wiki/Joseph_Kittinger
http://en.wikipedia.org/wiki/Michel_Fournier_(Adventurer)