In Kingston, he met Henry "Raleigh" Gordon and Nathaniel "Jerry" McCarthy, forming a group whose early recordings were attributed to "The Flames" and, possibly, "The Vikings". Having renamed the group the Maytals, the vocal trio recorded their first album, "Never Grow Old - presenting the Maytals", for producer Clement "Coxsone" Dodd at Studio One in 1962-63. With musical backing from Dodd's house band, the legendary Skatalites, the Maytals' close-harmony gospel singing ensured instant success for the 1964 release, overshadowing Dodd's other up-and-coming gospel trio, The Wailers. The original album augmented by studio out-takes from the Studio One sessions was re-released by Heartbeat/Rounder Records in 1997, and is essential listening for Maytals and Skatalites fans.
After staying at Studio One for about two years, the group moved on to do sessions for Prince Buster (released in 1974) before recording their second album produced by Byron Lee in 1965. However, the band's musical career was rudely interrupted in late 1966 when Hibbert was arrested and imprisoned on drugs possession charges.
Following Hibbert's release from jail towards the end of 1967, the band officially changed their name to Toots and the Maytals and began working with Chinese-Jamaican producer Leslie Kong, a collaboration which produced three classic albums and a string of hits throughout the late sixties and early seventies - "Do the Reggay", a 1968 single widely credited with coining the word reggae, "Pressure Drop", "54-46 was my number" and "Monkey Man", the group's first international hit in 1970. The group was featured in one of reggae's greatest breakthrough events - The Harder They Come, the 1972 film and soundtrack starring Jimmy Cliff.
Following Kong's death in 1971, the group continued to record with Kong's former sound engineer, Warwick Lyn; produced by Lyn and Chris Blackwell of Island Records, the group released three best-selling albums, and enjoyed international hits with "Funky Kingston" in 1973 and "Reggae Got Soul" in 1976.
Toots and the Maytals' compositions would be given a second airing in 1978-80 during the reggae-punk and ska revival period in the UK, when the Specials included "Monkey Man" on their 1979 debut album and the Clash produced their version of "Pressure Drop", with other Maytals' covers being recorded by Sublime. Having toured throughout the world for many years, Toots and the Maytals disbanded in the early 1980s, but reformed in the early 90s to continue touring and recording successfully.
The band recently won the 2005 Grammy award for reggae for the album True Love, an album consisting of re-recorded versions of their classics alongside popular and legendary musicians such as Bonnie Raitt, Willie Nelson, Eric Clapton, and Keith Richards, as well as popular artists today such as No Doubt, Ben Harper, The Roots, and Shaggy.
They also contributed to the album 'Radiodread' (a tribute to Radiohead's OK Computer).