Near the end of his life, Holmes attained notoriety for his reputed involvement in the Wonderland murders of July 1981 and eventually for his death from complications caused by AIDS in March 1988. He was the subject of several books, a lengthy essay in Rolling Stone and two feature-length documentaries, and was the inspiration for two Hollywood movies (Boogie Nights and Wonderland).

Holmes began his pornographic movie career in the late 1960s while he was unemployed and recovering from his collapsed lung. He frequented a men's card playing club in Gardena where on one evening, he allegedly met a photographer while standing next to him at a restroom urinal who gave Holmes his business card, telling him that he could find work in the underground adult film business. From 1969, Holmes did nude modeling for underground adult magazines as well as occasional stag films.

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With the success of Deep Throat (1972), Behind the Green Door (1972) and The Devil in Miss Jones (1973), porn became chic even though its legality was still hotly contested. Holmes was arrested during this time for pimping and pandering, but he avoided prison time by reputedly becoming an informant for the Los Angeles Police Department (LAPD).[11] Holmes' "handler" during his time as an informant was LAPD vice detective Thomas Blake. Of his involvement with Holmes, Blake said, "It was a pleasure working for him."[12]

By the late 1970s, Holmes was reputed to be earning as much as $3,000 per day as a porn performer.[6][11] Around this time, his consumption of cocaine and freebasing were becoming an increasingly serious problem. Professionally, it affected his ability to maintain an erection. To support himself and his drug habit, Holmes ventured into crime, selling drugs for gangs, prostituting himself to both men and women, as well as committing credit card fraud and various acts of petty theft. In 1976, Holmes met 15-year-old Dawn Schiller, whom Schiller later claimed he groomed, abused and forced into prostitution to support his drug habit.[13][14][15]

Holmes' signature asset in the adult film business was his exceptionally large penis. No definitive measurement or documentation verifying his penis' length or girth exists, leaving its exact size unknown. Holmes was uncircumcised.

Veteran porn actress Dorothiea "Seka" Patton has said that Holmes' penis was the biggest in the industry.[22] In the documentary film Exhausted, she described oral sex with Holmes as similar to fellating a telephone pole.[23] Holmes' first wife recalled his claiming to be 10 inches (25.4 cm) when he first measured himself in her presence.[24] On another occasion, Holmes claimed his penis was 16 inches (40.6 cm) long and 13 inches (33.0 cm) in circumference.[24] Holmes' long-time friend and industry associate, Bill Amerson, said, "I saw John measure himself several times; it was thirteen-and-a-half inches [34.3 cm]. The head was the size of an apple."[6] In contrast, medical studies of human penis size have consistently found erections average between about five and six inches,[25][26][27] with fewer than 0.2% of penises 9.5 inches (24 cm) or more.[28]

Another controversy was regarding whether Holmes ever achieved a full erection, although much of his early work clearly revealed he was able to achieve a substantial erection. A popular joke in the 1970s porn industry held that Holmes was incapable of achieving a full erection because the blood flow from his head into his penis would cause him to pass out.[31] Fellow film actress Annette Haven stated that his penis was never particularly hard during intercourse, likening it to "doing it with a big, soft kind-of loofah".[31]

After his release from Los Angeles County Jail for contempt of court in November 1982, Holmes quickly resumed his film career with a new generation of porn stars. His drug addiction continued off-and-on, and although work was still plentiful, it was no longer as lucrative as it had been with the advent of cheaply made videotapes that saturated the porn market. Most of the adult films and videos he made during the 1980s were little more than cameo appearances.

During the summer of 1986, Holmes was offered a lucrative deal from Paradise Visuals, who were unaware he was HIV-positive, to travel to Italy to film what were to be his last two pornographic films. Holmes' penultimate film was The Rise of the Roman Empress (originally released in Italy as Carne bollente) for director Riccardo Schicchi. The film starred Holmes, the later Italian Parliament member Ilona "Cicciolina" Staller, Tracey Adams, Christoph Clark and Amber Lynn.[41] His final film was The Devil In Mr. Holmes, starring Adams, Lynn, Karin Schubert and Marina Hedman.[42] These last films created a furor when it was revealed later that Holmes had deliberately concealed his HIV status to his co-stars before engaging in unprotected sex for the production.[41][43][44][45] Not wanting to reveal the true nature of his failing health, Holmes claimed to the press that he was suffering from colon cancer.[19]

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