I recently posted a video showing a contrail moving across the Sun; I just missed getting the airplane that made it jetting directly across the Sun’s face.
In 2012, Dean and Melinda Ketelsen had better luck. While testing out their camera rig just minutes before a solar eclipse began, they got this shot:
Looking over fighter silhouettes, I strongly suspect it’s an F-18, but I’m not sure. Given the size of the plane relative to the Sun, I’d wager it crossed the Sun in less than 1/10th of a second. The picture was taken at 1/2,000th of a second, sufficient to freeze the plane’s motion pretty well. Had her timing been off even a tiny amount, she would’ve missed it. It’s a total coincidence, but a very cool one.