Although he’s a little too far away and a little too blurry to be sure, apparently the guy pictured here sitting on a curb in the Hollywood Hills with the Hollywoodland sign in the background is Charlie Chaplin in 1926. The sign would have only been 3 years old at this point, so regardless of whether it’s Charlie or not, it’s interesting to see the sign so fresh and new, and the Hollywood hills so empty.
In this aerial shot of the Hollywoodland sign, we can see the farmland of Burbank in the San Fernando Valley on the north side of the Hollywood Hills. This was taken circa 1924, so the sign would only have been around a year old and Burbank was still mainly farms. Someone has thoughtfully inscribed the name of the streets. Directly above the ridge, where we can see Olive and Alameda is where the Walt Disney studios are now.