Wailer had originally gone to audition for
Leslie Kong at Beverley's Records in 1962, around the same time his step-brother Bob Marley was cutting "Judge Not". Wailer had intended to sing his first composition, "Pass It On", which at the time was more
ska-oriented. However, Wailer was late getting out of school and missed his audition. A few months later, in 1963, he formed "The Wailing Wailers" with Marley and friend Peter Tosh, and the short-term members
Junior Braithwaite and
Beverley Kelso. Wailer tended to sing lead vocals less often than Marley and Tosh in the early years, but when Marley left Jamaica in 1966 for
Delaware in the US, and was briefly replaced by
Constantine "Vision" Walker, Wailer began to record and sing lead vocals on some of his own compositions, such as "Who Feels It Knows It", "I Stand Predominate", and "Sunday Morning". Wailer's style of music was influenced by
gospel music and the soul singer
Curtis Mayfield. In 1967, he recorded "This Train", based on a gospel standard, for the first time, at
Studio One. Wailer was arrested on charges of possession of
cannabis in June 1967 and served a 14-month prison sentence. Around this time he, Bob Marley, and Peter Tosh signed an exclusive recording agreement with Danny Sim's
JAD Records and an exclusive publishing agreement with Sim's music publishing company Cayman Music. As the Wailers regularly changed producers in the late 1960s, Wailer continued to contribute songs to the group's repertoire. The music critic
Kwame Dawes says that Wailer's song lyrics were carefully crafted and literary in style, and he remained a key part of the group's distinctive harmonies. Wailer sang lead on such songs as "Dreamland") "Riding High", "Brainwashing", In 1971, the Wailers recorded Bunny Wailer's song "Pass It On", which he said he wrote in 1962; This version of the song features different lyrics and music in the verses to the later versions of "Pass It On" – Wailer would later reuse these in "Innocent Blood". By 1973, each of the three founding Wailers operated his own label, Marley with
Tuff Gong, Tosh with H.I.M. Intel Diplo, and Bunny Wailer with
Solomonic. He sang lead vocals on "Reincarnated Souls", the B-side of the Wailers first
Island single of the new era, and on two tracks on the Wailers last trio LP, "
Burnin'": "Pass it On" and "Hallelujah Time". By now he was recording singles in his own right, cutting "Searching For Love", "Life Line", "Trod On", "Arab Oil Weapon", and "Pass It On" (a new recording of the Wailers song) for his own label. and adopted the name "Bunny" in pursuit of a solo career after balking when
Chris Blackwell wanted the Wailers to tour
freak clubs in the United States, stating that it was against his
Rastafari principles. Before leaving the Wailers, Wailer had become more focused on his spiritual faith. He identified with the Rastafari movement, as did the other Wailers. He also composed much of his own material as well as re-recording a number of cuts from the Wailers' catalogue. Wailer recorded primarily in the
roots style, in keeping with his often political and spiritual messages; his album
Blackheart Man was well received. According to the journalist Peter Mason, writing in the Guardian newspaper, Blackheart Man "is widely felt to be one of reggae's highest peaks". ==Solo career==