After a successful audition for Coxsone Dodd, their career took off immediately with their first single, the classic "Simmer Down." Early on, all four of the boys contributed songs to the group, which enabled the Wailers to continue without Marley after he left Jamaica in 1966, to seek work for a time in the U.S. By then, the group had been reduced to a trio with the departure of Braithwaite, Green, and Kelso, but the core unit was so talented, that the temporary loss of one member never threatened their ascendancy. Over time, however, Livingston's songwriting contributions to the group had lessened, although when he did turn his hand to composing, the results were never less than scintillating. Marley, of course, was more than happy to pick up the slack. By 1973, the Wailers were untouchable, the biggest reggae band in Jamaica, and on the verge of an international breakthrough. Which is when it all went to hell. Life on the road is tough at the best of times, but the group were used to traveling the tiny distances between Jamaican (mostly Kingston) clubs. Now they were off on their first headlining tour outside the island. The first leg was a three month jaunt across the U.K., followed by an outing to the U.S. Livingston would never make that second leg, he barely made it through the first. Tensions were rising within the Wailers, a situation exasperated by the tour. Livingston had enough, and upon the group's return to Jamaica, he announced that he would not accompany the band to the U.S. His real reasons remain unknowable, the one ofttimes given, that his religious beliefs did not permit the eating of processed food, and what else could one eat on the road, doesn't hold much water.

Certainly the Wailers had somehow managed to obtain appropriate foodstuffs during the group's tour opening for Johnny Nash two years earlier. Whatever his true rationale, Livingston wanted off the road, at least outside the island, he intended to continue touring with the band in Jamaica. How this would have actually worked in the long run remains a moot point, before the year was out, Tosh had come to blows with Marley and quit the band. The Wailers were no more. (They would however make two final live appearances at benefit concerts after their official demise.) Livingston now began pursuing a solo career. He launched his own label, Solomonic, with his debut solo single "Searching for Love," in 1973. The next year saw four more join it, "Trod On," "Lifeline," "Arabs Oil Weapon" (which was actually released credited to the Wailers), and "Pass It On" (an alternate version to the one found on the Wailers' Burnin' album). In 1976, these releases were finally joined by Livingston's first solo album, the phenomenal Blackheart Man. The singer was accompanied by Tosh and the Barrett brothers -- the Wailers' own rhythm section, as well as Marley who joins in on a new version of the Wailers old number "Dreamland." Filled with a clutch of crucial songs, the album spun off two seminal singles, "Battering Down Sentence" and "Rasta Man." Protest and Struggle proved quick follow-ups over the next two years, and together with Livingston's debut, the trio of albums made for a militant manifesto of his deepest held political and religious convictions. Even though all three albums were released by the Island label, which had early on struck a distribution deal for Livingston's Solomonic label, and were well received by the press, none would have the impact that Tosh and Marley's releases were garnering.

Remaining in Jamaica, Livingston's profile would be forever overshadowed by his globe-trotting former bandmates. 1980's In I Father's House, did nothing to change this situation, nor did the singles which had appeared across this period. "Bright Soul," "Rise and Shine," and "Free Jah Children," amongst others, all barely registered outside the island. This same year, Livingston recorded Bunny Wailer Sings the Wailers, a tribute to his former group, lovingly revisiting his own favorites, accompanied by the Sly & Robbie led Roots Radics. By the time the album was released later in 1980, Marley's cancer had been diagnosed, the following spring he was gone. If that album had been a tribute to the band, the next was meant to honor his late friend. Tribute to the Hon Nesta Marley was drawn from the same sessions as had produced Bunny Wailer Sings, and again was determined to help keep the Wailers' legacy alive. Of course, in the end there was no need for Livingston to fear, since Marley's death, shelves have been warped under the weight of Wailers' reissues, but in the early '80s, it's understandable that Livingston was concerned that the group's music might have disappeared forever into the archives. However, the singer wasn't content to merely look to the past, and his second release for 1981, Rock'n'Groove, turned to the dancehalls for inspiration. Unfortunately, Livingston hadn't quite come to the grips with the new rhythms flooding from their, while sadly, 1982's Hook Line & Sinker didn't make a much better impression. In fact, the artist's best performance that year wasn't in the studio at all, but onstage. In December that year, Livingston finally stood on a stage again, for the first time since the Wailers had reunited way back in November 1975, as co-headliners with Stevie Wonder of a benefit concert for the Jamaican Institute for the Blind. Anyone witnessing this show was left dumbfounded on why the singer had stayed away so long. His ferocious performance took place in Kingston, of course, and was captured on tape for 1983's Live album. Again Livingston was accompanied by the Roots Radics, who had been acting as his backing band over the last few years, ever since they'd initially joined the singer for Bunny Wailer Sings... In 1985, the entrancing Roots Radics Rockers Reggae released, with the band now gaining equal billing to the singer. This same year, Livingston inked a distribution deal with the U.S. label Shanachie, which was inaugurated with the Marketplace album. It wasn't the best of debuts, and the singer sounds decidedly discomforted by the slick electronics and glossy production that steam across the record. Still, Livingston was determined to at least attempt to keep up with Jamaica's ever shifting musical styles and fashions.

Although not always successful, the singer was never tempted to wallow in the past, and has consistently given a sympathetic ear to the latest innovations in production and rhythms. Then, in 1986, Livingston broke with past tradition entirely, and finally undertook his first tour outside of Jamaica since the debacle with the Wailers back in 1973. His American debut took place in Long Beach, CA, that July, with his later appearance in New York recorded for the In Concert video. The next year, the singer unleashed two new albums, Rootsman Skanking and Rule Dance Hall, both boasting a strong and confident dancehall flavor. It had taken a few goes, but Livingston had finally come to grips with the dancehalls, and a pair of singles, "Cool Runnings" and a recut "Rock'n'Groove," proved the point, both soaring up the Jamaican charts. Having accomplished that, Livingston now, almost perversely, returned to an older sound for 1989's equally wonderful Liberation, eschewing the dancehall flavors for a return to a rootsier past. This turned out to be his most acclaimed album of the decade, and in response the singer set off on a world tour, with backing now provided by the recently reformed Skatalites. The singer opened the new decade with another heartfelt album in honor of his late friend, Time Will Tell: A Tribute to Bob Marley. The disc would garner Livingston a Grammy. And 1990 really was a stellar year, with the singer also making his debut appearance at the Reggae Sunsplash Festival. 1991 brought the Gumption album, another covers' set, but this time from a variety of artists, including Toots Hibbert and Johnny Clarke. The following year, Livingston returned to the present with a vengeance with Dance Massive, a joyous dancehall album, where the taut rhythms virtually overwhelm the songs. Just Be Nice followed hot on its heels in 1993. It was another two years before a new album arrived. Hall of Fame: A Tribute to Bob Marley's 50th Anniversary was a double album, featuring 52 songs, all loving recreations of Marley's Wailers' and solo compositions. Accompanied by a phenomenal aggregation of Jamaican sessionmen, the set would garner the singer another well deserved Grammy.

Meanwhile, Livingston was beginning to turn more of his attention towards politics. He has shown an especial interest in youth issues, and eventually formed his own political party, the United Progressive Party. The U.P.P. platform calls for the decriminalization of marijuana, but of equal importance, also offers up numerous educational reforms. The artist's heavy involvement in politics kept him out of the studio for much of the rest of the decade, but he finally returned in the new millennium with an exciting album, Communication.