Slapstick Summer Series: The 1st Pie Face | Mr. Flip (1909)

Mr. Flip, played by cross-eyed comedian, Ben Turpin, is quite the ladies' man...and by "ladies' man", I mean borderline sexual harasser who constantly receives his just desserts [sp]. Speaking of which, this film (directed by Gilbert M. "Broncho Billy" Anderson) includes the earliest known use of the pie-in-the-face bit in a movie.

http://www.imdb.com/title/tt0236517/