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In 1921, the Hollywood Legion Post #43 open the Hollywood Legion Stadium on El Centro Ave. to promote boxing. Over the course of several years, the boxing at the the stadium drew many hollywood celebrities, such as Charles Chaplin, Rudolph Valentino, Douglas Fairbanks, Jean Harlow, and Claudette Colbert.
The most tragic event involving the Hollywoodland sign was the suicide of Millicent Lilian "Peg" Entwistle. On September 16, 1932, Peg climbed the letter "H" of the Hollywoodland sign and jumped to her death. Peg was a talented actress with a promising career, but devastating personal and career issues took it toll on her spirit. She was only 25 years old.
 For some unknown reason, the intersection of Hollywood Blvd. & Vine St. became someone iconic as a symbol of Hollywood's popularity. By 1935, there were three high rise buildings and a single story building on the four corners of this intersection. Here is a 1924 photo of the intersection.
The first Brown Derby Restaurant was opened in 1926. Located on Wilshire Blvd. the restaurant's building was in the shape of a derby. Three years later, a second Brown Derby restaurant was opened on Vine St. in Hollywood. This photo was taken in 1927. 
Jean Harlow's real name was Harlan Carpenter and she attended the Hollywood School For Girls in 1923-24. Considered one of Hollywood's first "blond bombshell", she was in films with some of Hollywood's most popular leading men. Four years after this 1933 photo was taken of her placing her hand and footprints in the Chinese Theater's forecourt, she passed away of uremic poisoning and Kidney failure in 1937.

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