Having only seen a few of Hitchcock's films, I can't say I saw any significance to his cameo appearances beyond being a "Where's Waldo?" as you put it Sola. However, if I were to guess at its significance, I would say he puts himself in there as his own way of signing his art. Films are art, and some directors even approach it the way they make paintings or drawings. Ridley Scott, David Lynch, David Cronenberg, Steven Spielberg, all great directors have some trademark to their films that is all their own. For some, it's in the mechanics, the way they make a film, while for others it has to do with certain themes to recur in either the visuals or the story. I think for Hitchcock, his appearances are like a signature, a little way of saying, "This is MY film. I am Alfred Hitchcock, and I am the man who has created this film." It might be a little egotistical, but it's Hitchcock. Beyond that, I can't see why his appearances in his films would be anything more than just fun.
Hitchcock's cameos are an interesting "display" of the auteur "not at work" as it were. Hitch is the consummate filmmaker and his style is so specific that his cameos are utterly unnecessary; they are a "feminine redundancy" of the man behind the camera. Hitch appears in at least 52 of 54 films, as does his signature brandy drink. He and brandy are an even more pervasive motif than, oh, let's say, birds. Hitch would usually appear somewhere deep in the story. It is vanity to be sure; he wanted to be "scene/seen" and his growing corpulence contributes to the bizarre necessity of displaying himself to his malleable audience. Hitch had a huge feminine side, whose "jealousy" would explain the plethora of unpleasant or wacky mother figures in his stories. But as more and more people cottoned on to his appearances in his films he knew they would be distracted from the story (Hitch became another set piece, like a carnival or rowboat or cliffside drive), and he ends up near the beginning in his later films. It's strange of course that Hitch, who wished to dominate the women around him also wanted to BE a woman. It's a lovely and standard corporate-transvestitie paradigm. And it's just fine! His greatest cameo is the fluid passing of ships in the night pose at the start of his THE BIRDS (1963). Tippi Hedren enters the birdshop as Hitch exits with his pet Sealyhams. I never tire of this moment, wherein Hitch displays himself, part man-bird preening, part aging socialite on a shopping spree, passing and almost touching Melanie Daniels (Hedren). Jodie Foster would use this electric flashpoint at the end of her LITTLE MAN TATE when her character and Dianne Wiest's finally touch at the little party. The man was vainglorious and he delivered. His cameos are discrete, discreet flashes of leg as it were, a demureness not seen in any other aspects of his craft.
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