According to some accounts, Grace made her first stage appearance in Chicago at the 1933 Century of Progress International Exposition. In 1935, she was chosen winner of a World's Ugliest Woman contest, which became the name under which she would initially be exhibited in sideshows. Grace, however, hated that name and successfully lobbied to be known instead as The Mule-faced Woman.

Grace's pride and joy was her son, Elmer, who appeared beside her on many of her pitchcards. A handsome boy, Elmer grew into the role of Grace's manager. However, Elmer became a drug and gambling addict whose abusive behavior and reputation were so egregious that eventually shows stopped hiring Grace because of him.

Like many showfolk, Grace retired to Gibsonton, Florida. She died a few days shy of her 70th birthday in March 1958. Advanced liver disease caused her ne'er-do-well son to follow Grace to the graveyard not long afterward.

My portrait of Grace McDaniels was based upon a circa 1470 painting in London's National Gallery called Portrait of a Woman of the Hofer Family by an unknown Swabian artist. This painting is notable for the prominent appearance of a housefly on the lady's otherwise immaculate headdress, the length of which reminded me of the veil Grace would often wear in public when off-the-clock. Mules attract flies, of course, so I added more to my tribute as well as additional equine references such as the horseshoe pendant at Grace's throat and a pattern in the background taken from a certain brand of borax laundry conditioner. Instead of the forget-me-nots in the original painting, Grace holds a sprig of the evergreen shrub Baccharis salicifolia, commonly known as mule fat.