While they never achieved the commercial success or cultural impact of the Wailers, Toots the Maytals were nearly as important in the history of Jamaican music. Like the Wailers, the Maytals thrived as ska gave way to rocksteady and then evolved into reggae, they boasted one of the island's finest singers and most charismatic frontmen in the great Toots Hibbert, and they worked with many of the most important producers and sidemen on the island. The Maytals were also the band that most clearly demonstrated the links between Jamaican sounds and American R&B (Hibbert's rich, emotive vocal style was informed by Otis Redding, Wilson Pickett, and other soul icons), and the group's catalog contains a number of crucial, frequently covered tracks, most notably the classic "Pressure Drop." The expanded reissue of 1965's The Sensational Maytals is a fine selection of their early ska sides; 1973's Funky Kingston and 1976's Reggae Got Soul are joyous, muscular classics that belong in any reggae fan's collection; and 1988's Toots in Memphis is a solo effort where Hibbert pays homage to the classic R&B that inspired him.

Toots the Maytals were founded by Frederick Toots Hibbert, who was born in May Pen, Clarendon Parish, Jamaica in 1945. Hibbert was the youngest in a family of seven children, and first took up singing as a member of the church choir. In 1961, Hibbert set out for Kingston and struck up a friendship with Nathaniel Jerry Matthias and Henry Raleigh Gordon, a pair of singers with a smattering of recording experience. The three formed a vocal group, and in 1962 they were discovered by producer Clement Coxsone Dodd, who signed them to his Studio One label. After releasing a debut single, "Hallelujah," under the name the Vikings, the trio became known as the Maytals, and beginning with "Fever," they issued a number of singles that were compiled into the 1963 album Never Grow Old. The Maytals' Studio One sides featured accompaniment by the legendary Jamaican band the Skatalites, and were dominated by strong, gospel-influenced close harmonies and Hibbert's soulful lead vocals. After two years with Studio One, the Maytals briefly worked with producer and ska pioneer Prince Buster before signing on with another Jamaican record man of note, Byron Lee, in 1965. The Lee-produced material showed that the Maytals were developing a more mature and polished approach, but the group hit a serious roadblock in 1966, when Hibbert was arrested for possession of marijuana; he was convicted, and would serve a year behind bars.

In 1967, Hibbert was a free man, and he reunited with Matthias and Gordon, renaming the group Toots the Maytals. Hibbert's stay in prison coincided with ska fading from the musical landscape in Jamaica as the proto-reggae sounds of rocksteady took its place. The new style suited Toots the Maytals, and they signed with producer Leslie Kong, with whom the band would record some of their biggest hits, including "Pressure Drop," "Sweet and Dandy," "Monkey Man," "54-46 (That's My Number)," and "Do the Reggay," the latter often cited as the song that gave the new style of music its name. When "Monkey Man" became a British hit in 1970, Toots the Maytals began enjoying success outside Jamaica for the first time, and in 1972, "Pressure Drop" and "Sweet and Dandy" were featured on the soundtrack of the film The Harder They Come, starring Jimmy Cliff. The movie was a smash in Jamaica and became an art house sensation in the United States, as the film and its soundtrack album helped make American listeners aware of the growing reggae phenomenon.

In 1971, Leslie Kong died, and Warwick Lyn, Kong's primary recording engineer, took over as the group's producer. Chris Blackwell, whose Island Records label was enjoying success releasing reggae material in the U.K. and U.S. (particularly Bob Marley the Wailers), also joined their production team, and before long he would sign the group to Island, releasing a revamped version of the album Funky Kingston in the United States in 1975. That same year, Toots the Maytals made their American concert debut opening a tour for the Who, though their stateside audience gave Toots a cool reception.

With the 1976 album Reggae Got Soul, Island hoped to open up Toots the Maytals to the R&B audience in America, but while the record was well received, their American following remained little more than a lively cult. The band focused on pleasing their Jamaican and British fans with their next two albums, 1979's Pass the Pipe and 1980's Just Like That, and they made their way into The Guinness Book of World Records with their next release, Live; recorded during a concert at London's Hammersmith Palais, an early limited-edition release of the LP was available in shops within 24 hours of the performance it captured. By this time, a new generation of fans was discovering the Maytals after the Clash covered "Pressure Drop" and the Specials included "Monkey Man" on their debut album.

Following the release of the 1981 album Knock Out!, the trio split up, and Matthias and Gordon retired from the music business, while Hibbert continued as a solo artist. Though Hibbert stayed busy as a live act, he didn't record again until 1988, when after playing a well-received set at the New Orleans Jazz & Heritage Festival, he was approached by the head of Mango Records about cutting an album of American soul and R&B classics. Toots in Memphis paired Hibbert with the powerhouse Jamaican rhythm section of Sly Dunbar and Robbie Shakespeare and members of the Hi Records and Stax Records studio bands. The album was enthusiastically received by critics and earned Hibbert a Grammy nomination.

In the mid-'90s, Hibbert assembled a new version of Toots the Maytals without Gordon and Matthias, and toured extensively while recording a handful of albums for various reggae specialist labels. Toots the Maytals made a high-profile comeback in 2004 with the album True Love, in which Toots re-recorded a number of his best and best-known songs with a stellar collection of guest stars, including Eric Clapton, No Doubt, Willie Nelson, Bonnie Raitt, Keith Richards, and the Roots. After this Grammy-winning collection of duets, Hibbert stepped back to the spotlight on his own for 2007's Light Your Light, and in 2012 his latest edition of the Maytals set out on a global acoustic tour to commemorate the 50th anniversary of their recording debut. A pair of concert albums, Reggae Got Soul: Unplugged on Strawberry Hill and Live! appeared that same year. After a 2013 incident in which Hibbert was hurt by a vodka bottle thrown by an intoxicated fan, he eased back on his career, performing occasionally but staying away from the studio. However, when noted musician and reggae fan Zak Starkey launched a new label, Trojan Jamaica, one of the first acts he signed was Toots the Maytals, and their first release for the company, Got to Be Tough, arrived in August 2020. Hibbert's comeback proved to be a last hurrah when he was hospitalized with COVID-19 symptoms shortly after the album's release. Toots Hibbert died in Kingston, Jamaica on September 11, 2020. ~ Mark Deming, Rovi