I used to spend a lot of time in the passenger seat of helicopters for work. Literally every time I got into a bird with a new pilot, I'd ask them to do a barrel roll. I learned a lot about the machines in their explanations as to why it was a bad idea, including interesting tidbits about the modifications to a red bull chopper in order to pull off the stunt (custom fixed rotor head, in case it matters). But it broke the ice with the pilots, and a few of them pulled off a few neat, but less dangerous, tricks.
My favourite probably dangerous trick was flying towards a hill and pulling up at the last moment, sort of bounding off your own ground effect wave (I don't know the proper jargon for this manoeuvre).
Having been in a few different plane cockpits, I often wonder how making a sign to be seen from the sky would actually be seen by a pilot unless they had windows in the floor (which I've only personally seen in small craft). A big old commercial passenger jet, you can't really see below you.
If we assume Calvin is ~1 m tall, the text can't be much more than 6 m Ć 10 m.
0.5Ā° / arctan (10 meters / 30000 feet) gives is about 1/8th the diameter of the full moon. This number would be smaller if the pilot is not directly overhead, and larger if the jet is not at cruising altitude (i.e. taking off or landing).