A sufferer of cystic fibrosis, Bob Flanagan was actually one of Jerry's kids. He lived much of his life in constant, humiliating pain. Then he discovered masochism, which he used to learn to love his pain.

In his own words, he used masochism to "Fight sickness with sickness". He used the physical humiliation he suffered in his medical treatments as an inspiration for the physical humiliation he would endure and depict in his art. He was, at different times, a comedian, a performance artist, and a more traditional artist. One of his art works is a collage of pictures taken of his face against a neutral background by his lover/dominatrix Sheree Rose. Some pictures were taken while he underwent medical treatment. Others were taken while being tortured by Rose. It is difficult to tell which are which.

At least one recipient of the Make A Wish Foundation gift considered Flanagan an idol to the disabled and infirm. She visited him in Southern California, and they went together to get her nipple pierced.

Bob Flanagan died at the age of 43. It was several years longer than the typical life expectancy of a cystic fibrosis sufferer.

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