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Lurkposition
How about high altitude record Irish jig fiddle playing by Mike O'Connor FL420 in a Mk1 Nimrod en route Jax to St Mawgan, mid Atlantic, 0100Z. Authenticated by Shanwick controller with a suitably broad Oirish accent asking very slowly "just exactly what are you guys doin' up dere at dis time o' night?"
BEagle
Possibly around your time on the V-force. Didn't a certain tall red haired AEO play the bagpipes at FL450? It actually made an inside page of the Telegraph I seem to remember, whereupon a po-faced spokesman sniffed that "Vulcans are not for fun". So you see there were Killjoys and Pecksniffs around then too.
The Ancient Mariner