possibly the first photobomber, which is a hoot, but wow, that nose art on the Sikorsky S-29 that was modified to resemble a German Gotha bomber in 1927 for the Howard Hughes movie

By the time of its release on May 27, 1930, Hell’s Angels had cost $2.8 million, becoming one of the most expensive movies made to date. Hughes inflated the production cost (and subsequent profits) for publicity purposes, but his splashy Hollywood premiere at Grauman’s Chinese Theatre remains unsurpassed. 

Thousands of spectators lined Hollywood Boulevard as speeding aircraft flew overhead, producing red, white and blue trails; stuntmen parachuted into the crowd; massive floodlights lit up the night sky; and 600 policemen along with National Guard troops were called in to control the frenzied crowd, clamoring to glimpse the small army of movie stars on hand for the spectacular gala event.

 https://www.jalopyjournal.com/forum/threads/vintage-shots-from-days-gone-by-part-2.1154030/page-799#post-13807264

https://www.historynet.com/how-hundred-takes-hughes-got-his-nickname.htm