Kenneth Leith Halliwell was born on June 23, 1926, in Bebington, Cheshire, on the Wirral Peninsula near Liverpool, England. Raised in a modest middle‑class household, he was an intelligent and sensitive child with a strong bond to his mother. When he was eleven years old, he witnessed her sudden death from a wasp sting—an event that profoundly affected his emotional stability throughout his life.

At Wirral Grammar School, Halliwell excelled academically, particularly in classics and literature, earning his Higher School Certificate in 1943. During World War II, he registered as a conscientious objector, refusing military service on moral grounds. As an alternative, he worked as a coal miner, a physically and psychologically punishing form of compulsory labor. After his discharge in 1946, he briefly acted in Scotland before returning to Birkenhead to perform in small local productions.

Tragedy again struck in 1949 when Halliwell’s father committed suicide by inhaling coal gas in the family home. Halliwell himself discovered the body the next morning—a trauma he appeared to repress. Accounts suggest he reacted with detached calm, reportedly making tea and shaving before notifying authorities, an anecdote often cited to illustrate his emotional suppression.

Inheriting a small family fortune after his parents’ deaths, Halliwell moved to London to study drama at the Royal Academy of Dramatic Art (RADA). Though talented and articulate, his social awkwardness and depressive tendencies limited his prospects as a professional actor.

In 1951, while both were students at RADA, Halliwell met Joe Orton, a young man from Leicester with little formal education but considerable natural wit. The two quickly became romantic partners and artistic collaborators. Halliwell, eight years Orton’s senior, served as mentor, intellectual guide, and domestic partner. They shared a flat in Islington, North London, and collaborated on writing projects that were initially rejected by publishers.

Their relationship—equal parts affection, dependence, and rivalry—was marked by creative highs and personal instability. In 1959, the pair were arrested for defacing and stealing public library books in a mischievous protest against literary censorship. Halliwell created surreal collages from the stolen dust jackets, while Orton wrote witty, subversive fake blurbs. In 1962, both men were convicted and sentenced to six months in prison—Halliwell to HM Prison Ford, Orton to HM Prison Eastchurch.

Prison separated them and left Halliwell particularly shaken. When they were released, Orton’s career soon flourished: his plays Entertaining Mr. Sloane (1964) and Loot (1965) made him a celebrated figure in British theatre. Halliwell, by contrast, drifted into depression, frustrated by his own lack of recognition and increasingly overshadowed by Orton’s fame.

By 1966–67, Halliwell’s mental health had deteriorated. He suffered from anxiety, paranoia, and severe jealousy, convinced that Orton’s success—and his numerous sexual encounters with other men—had humiliated him. He was prescribed antidepressants and sedatives, including Nembutal (pentobarbital), and frequently complained of insomnia. 

In the early hours of August 9, 1967, Halliwell struck Joe Orton multiple times on the head with a hammer while he slept in their flat at 25 Noel Road, Islington. Forensic reports indicated nine blows, one of which fractured the skull and proved fatal. Halliwell then ingested a fatal overdose of Nembutal sleeping pills, dying several hours before Orton.

Their bodies were discovered late the next morning when a chauffeur arrived to take Orton to a meeting with film director Richard Lester, who had been planning a Beatles project based on Orton’s screenplay Up Against It. Police found Orton’s body lying in bed and Halliwell’s body nearby, along with a suicide note reading:

“If you read his diary, all will be explained. KH — P.S. Especially the latter part.”

The “diary” referred to Joe Orton’s journals, which detailed his numerous sexual affairs and his growing irritation with Halliwell. These entries revealed the emotional imbalance between the two men and are widely believed to have triggered the fatal confrontation.