Charlie Chaplin and the Brooklyn stenographer Mary Louise Gribble, transformed by Chaplin into Hollywood’s Joan Barry.

Lady and the Little Tramp

Among Charlie Chaplin’s many ill-fated trysts, perhaps his most disastrous was with Joan Barry, a woman 30 years his junior

By Diane Kiesel

Photo illustration by Chop Choppish Shop

In 66 silent movies between 1914 and 1936, Charlie Chaplin, as the Little Tramp, found himself in desperate situations: surviving on a shoestring (literally, in The Gold Rush); losing his pants while performing on the high wire (The Circus); and stumbling upon an abandoned baby in an alley (The Kid). Ever resourceful, his beloved character always overcame disaster in time for the next movie. Not so in real life, where his skills failed him in 1944 as he faced years in prison on a federal Mann Act charge.

Handsome when not in costume, Chaplin was catnip to women and reckless in his assignations. His first two marriages (to Mildred Harris and Lita Grey) were at the end of a shotgun, but it was a pistol-packing protegée, disappointed at being dumped, who ignited the fuse that exploded on Chaplin.