Louis Burton Lindley Jr. was born in Kingsburg, California, the son of Sally Mosher (nee Turk) and Louis Bert Lindley Sr., a Texas-born dairy farmer. Young Lindley was an excellent horse rider from an early age. Known as "Bert" to his family and friends, he grew bored with dairy farming and began to make a few dollars by riding broncos and roping steers in his early teens. His father found out and forbade this activity but he took no notice, went to compete in a rodeo, and was told by the doubtful rodeo manager that there would be "slim pickin's" for him.

Pickens played B-52 pilot Major T. J. "King" Kong. in Dr. Strangelove. Stanley Kubrick cast Pickens after Peter Sellers, who played three other roles in the film, sprained his ankle and was unable to perform in the role due to having to work in the cramped cockpit set. Pickens was chosen because his accent and comic sense were perfect for the role of Kong, a cartoonishly patriotic and gung-ho B-52 commander. He was not given the script to the entire film, but only those portions in which he played a part. Three memorable scenes featuring Pickens were:  A monologue meant to steel the crew for their duty after he receives the definitive inflight order to bomb a strategic target in the USSR  Reading aloud to his crew the contents of their survival kits (possibly the first mention of condoms in a Hollywood film): After listing the contents usable for barter with Russian women (prophylactics, nylons, lipstick, etc.), as well as a .45 automatic pistol, Major Kong said, "Shoot, a fella could have a pretty good time in Big D [Dallas] with all this stuff." This line had to be looped (the reference to Dallas changed to "weekend in Vegas") after the November 22, 1963, screening for critics was cancelled due to President John F. Kennedy's assassination.  Best known of all, Pickens riding a dropped H-bomb to a certain death, whooping and waving his cowboy hat (in the manner of a rodeo performer bronc riding or bull riding), not knowing its detonation will trigger a Russian doomsday device  Pickens credited Dr. Strangelove as a turning point in his career. Previously, he was "Hey you" on sets and afterward he was addressed as "Mr. Pickens". He once said, "After Dr. Strangelove, the roles, the dressing rooms, and the checks all started gettin' bigger." Pickens said he was amazed at the difference a single movie could make. However, Pickens also said that working with Stanley Kubrick proved too difficult due to Kubrick's perfectionist style of directing with multiple takes for nearly every shot, especially with the climactic H-bomb riding scene, which was done in just over 100 takes. In the late 1970s, Pickens was offered the part of Dick Hallorann in Kubrick's adaptation of Stephen King's The Shining, but Pickens stipulated that he would appear in the film only if Kubrick was required to shoot Pickens' scenes in fewer than 100 takes. Instead, Pickens' agent showed the script to Don Schwartz, the agent of Scatman Crothers, and Crothers accepted the role.

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