As an actress, Menken became an early master of self-promotion. According to historian Alan Ackerman, she made certain that a photograph of her striking face appeared in shop windows in every city in which she performed. Even in the context of the 1860’s, when most Americans looked upon actors as loose" and disreputable, Menken was notorious for violating norms. She cropped her dark hair close to her head (she may have been the first important American woman to do so) and smoked cigarettes in public.

Even more unladylike, Menken openly defied conventional married life, marrying four men in the space of seven years. Her second marriage, in 1859 to world heavyweight boxing champion John C. Heenan, led to the birth of a son, who died in infancy. Eight years later, a son by her fourth husband suffered the same fate.

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