Flanagan was born in New York City on December 26, 1952, and grew up in Costa Mesa, California, with his mother, Kathy; father, Robert; brothers John and Tim; and sister, Patricia.
"[7] Visiting Hours, first shown at the Santa Monica Museum of Art in 1992, combined text, video, and live performance, and explored the convergence of illness and SM.
[8] According to curator Laura Trippi, "The installation is designed like a crazy stage set of a children's residential hospital, replete with a torture chamber lurking amidst the institutional cheer.
In the video, a nude Flanagan is bound to a mechanical torture device which pierces his flesh, pulls on his nipples and penis with pincers, crushes his genitals with a paddle, and ultimately kills him.
In the uncensored version of the video (near the ending), Flanagan pierces his upper and lower lips together and then he hammers a nail through the head of his penis before bleeding on the lens of the camera recording him.
Flanagan also had a small role in Godflesh's "Crush My Soul" video, as an upside-down suspended Christ, hoisted on to the ceiling of a church by Sheree Rose.