Jennings published his next novel, The Cowboys, in 1971. The previous year, director Mark Rydell, who had read a plot summary, persuaded Warner Brothers to buy the movie rights to the story. As well as writing the novel, Jennings contributed to the film script. The project was not without controversy.

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The Cowboys tells the tale of a rancher, played in the movie (1972) by John Wayne, who enlists a group of teenaged boys as cattle-drivers after his original crew decamps to join a gold rush. The situation is clearly at least , but editors at Bantam called for the elimination of any trace of .

Jennings resisted, arguing that his work reflected the reality of frontier life. One editor conceded that "for all I know, this story may depict [sexual practices] accurately" but nevertheless urged the "judicious cutting" of passages on subjects he viewed as "taboo." Another wrote to Jennings, "The intimations of adolescent homosexuality are distracting. Either they should be more clearly spelled out or considerably toned down. And frankly I urge the latter."

Although Jennings made some revisions, Bantam finally rejected The Cowboys, as did Putnam. Stein and Day eventually accepted and published the novel, to which Jennings retained the copyright.

The last of Jennings's novels to make it into print was The Sinking of the Sarah Diamond (1974), an adventure story about a singularly ill-starred cargo vessel that floats from one disaster to another. Reviewer Martin Levin of the New York Times praised the "slick . . . storytelling" that made "a buoyant novel out of a sinking ship." Despite favorable reviews, the book was not a great success.

The Cowboys, on the other hand, had given Jennings the resources to buy a ranch near Los Angeles and later to move to northern California. A lawsuit by a former lover cost him his home and most of his assets, however, and he returned to Los Angeles.

Hat in hand, in 1985 Jennings turned to an old friend from ONE, Slater, who had since left the organization and founded the Homosexual Information Center (HIC) in 1965. Jennings had served on the HIC board and contributed articles to its journal, Tangents. His purpose in reconnecting with Slater was twofold: to request that the HIC preserve his writings and also to seek a job.

Slater was unable to offer Jennings employment, but the HIC accepted his collection, which was a great relief to him. He continued adding to his writings until his last days, although the process became increasingly difficult for him in the mid-1990s when his memory began to fail. At that point he bequeathed all he had to the HIC.

Toward the end of his life Jennings was reclusive and suspicious of care-givers, fearful that they might destroy his cherished archives. One person whom he trusted was Jim Schneider, a veteran activist and member of both ONE and the HIC, who cared for him in his final years and was present when he died of respiratory failure on May 11, 2000.

A memorial service was held for Jennings the next month at the ONE Institute and Archives, into which the HIC had moved and where Jennings's writings are now housed.

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