EricMc: It was Sideshow Bob who stole a Wright Flyer, although Homer did once masquerade as a pilot to driink, got volunteered to a flight and wound up retracting the undercarriage while stationary... D'oh!

Of course you're correct. And he crashed it too from what I remember. Therefore, we should be adding Kelsey Grammar (Spl?)to the list.

Always - Hi Y'all Holly has been mentioned - but Richard Dreyfuss and John Goodman reminded me of me and another bloke I used to instruct with, in that order...

Always: what a top film ,has to be one of the best openings in any flying film , great flying and great humor

Regarding Jimmy Stewart,

An aviation magazin in early 90's had a more detailed story about his flight experience. If my poor brain remember it right, PIC in B-24 in combat, SIC B-17 non combat, PIC B-47 in early 50's but never in B-36 (but did of course get some stick time during shooting of SAC). His B-52 flight in Nam was mentioned, it was a one time only as a non duty crewmember!

I suppose you could add Jerry Lewis in "The Family Jewels". A shortish vignette, about a strange looking character who flew a group of harpies to Vegas in a tri-motor.