The best documentation of the 1914 Vanderbilt Cup Race is a Mack Sennett-produced slapstick comedy starring Mabel Normand, Ben Turpin and Charlie Chaplin called Mabel at the Wheel. Actual scenes of the race, won by Ralph DePalma in a Mercedes, were used as part of the film.
A 2008 book Chaplin by Dr. Stephen Weissman has detailed the significance of this film in the careers of Charlie Chaplin, Mabel Normand and Mack Sennett:
It was true that the film Chaplin boycotted (on the first day of shooting) was Mabel Normand's maiden voyage as a director. Mabel at the Wheel was a comedy "vehicle" with feminist undertones in which Normand played a capable lady racetrack driver who succeeds in foiling the bungling slapstick attempts of an oily male villain to fix the outcome of the race. A very reluctant and out-of-character Charlie was cast by Mabel to play the heavy to her juicier role as the film's comic heroine.
The next day, Mack Sennett coaxed Chaplin into agreeing to cooperate with Mabel for the "good of the picture," in exchange for a semipromise that, in the near future, he could write and direct a movie of his own. Delighted at the possiblity of gaining artistic independence to explore and to develop his own brand of comedy, Charlie became all sweetness and tractability. Stepping in gallantly to help his girlfriend to write, direct and act in her directorial debut, Mack was able to restore an atmosphere of mutual respect and creative curiosity.
Click here to see highlights of the 1914 Vanderbilt Cup Race as seen in Mabel at the Wheel.