He has worked with Theophilus Beckford, Jimmy Cliff, Monty Alexander, Prince Buster, the Skatalites, Bob Marley and the Eric Deans Orchestra.

While performing locally with these orchestras, Ranglin was introduced to the jazz pianist Monty Alexander, which led to a lifelong friendship as well as numerous musical collaborations.

The 1958 albums The Wrigglers Sing Calypso at the Arawak as well as Jamaica Fabulous Island in the Sun - Denzil Laing and the Wigglers Sing Again (Kalypso FR 1002) recorded at Federal Studio are representative of the type of calypso floor show that Jamaican bands performed at hotels (some of the tracks from the original albums are included on the 2010 CD release Jamaica - Mento 1951–1958).

[10][11] In 1963, Ranglin played guitar on and arranged "My Boy Lollipop", which was sung by Millie Small, who had recently been signed to Blackwell's Island label.

"My Boy Lollipop" (a cover version of a song written by Robert Spencer of the doo-wop group the Cadillacs and originally recorded by Barbie Gaye in 1956) became a worldwide hit after being released by Island on licence to Fontana in March 1964.

Initially the manager of Ronnie Scott's was reluctant to agree but eventually allowed Ranglin to sit-in with the house band.

[6][14][1] The closing years of the sixties found Ranglin working with the Jamaican producers Lee "Scratch" Perry and Clancy Eccles; both of whom were instrumental in developing and establishing the new genre of reggae.

In 2002 Ranglin was awarded an Honorary Doctorate Degree from the University of the West Indies for his outstanding contribution to the development of music in Jamaica.

[23][24] In 2008, Ranglin was inducted into the Jamaican Music Hall of Fame by the Jamaica Association of Vintage Artistes and Affiliates (JAVAA).

The tour featured musicians including Tony Allen, Courtney Pine, Ira Coleman, Cheikh Lô and Alex Wilson.