Influenced by the sounds of Stevie Wonder, the legendary Bob Marley, Alton Ellis, Ken Boothe, Bob Andy and many others, Freddie finessed his talent with early tracks like Why Did You Do It and Do Good and Good Will Follow You. In the mid-sixties he teamed up with Ernest "Fitzroy" Wilson to form the duo Freddie and Fitzroy while he continued to develop his craft. In 1975, Freddie's musical and lyrical content changed with a strong slant towards lyrics of social consciousness with tunes like Mark of the Beast, I Am A Rasta and reggae classic Bobby Babylon. In 1977 Freddie released his long awaited album Mr. McGregor, which contained reggae mainstays such as Zion Chant, Rastaman Chant and Walls of Jericho. This album marked a major milestone in his stellar career and in 1981 his tune Big Ship became one of reggae's biggest hits, earning him a permanent place in reggae music history.

In 1989, Freddie launched his own record label, Big Ship, featuring Jamaica Classics Volume One as the first major release. Part of this compilation included popular tunes like Little Roy's Prophecy and Derrick Harriot's The Loser. Today, Big Ship is the largest and most recognized reggae label in Japan handling its own production, manufacturing, distribution and promotions. To date, Big Ship has produced several reggae artists including General Degree, Cutty Ranks, Mikey Spice, Benjy Myaz and Freddie’s daughter Yeshemabeth. His album entitled Anything For You featuring the songs Uncle Sam, I See It In You and Anything for You, was nominated for a Grammy. Recently Freddie produced the historic Super Stars Extravaganza DVD, highlighting rare concert footage from the 1989 Denbigh Show Ground (May Pen, Clarendon, Jamaica). The DVD features live performances by the great Dennis Brown, Gregory Isaacs, Cocoa Tea, Barrington Levy, Frankie Paul, Carlene Davis and the legendary Tamlins.

Over the years, Freddie has consistently “given back” to the community in many ways. He produces his own concert entitled RockSteady Meets Reggae, which promotes unity within the reggae fraternity. He also donates to charities throughout the world and manages his own US and England based children's organizations; Big Ship Foundation Inc. and the Freddie McGregor Children’s Fund, both of which provides services and funding to renovate schools.

Freddie McGregor continues to please reggae fans and music lovers throughout the world headlining international concerts and venues including Poland's Blue Note, Japan's Jumping Splash, Reggae Sunsplash (Clapham Common), the Cartegena Festival (Colombia), Midem (France), the Jamaican Expo (performing for Nelson Mandela and Prince Charles), the London Hammersmith Apollo - performing with John Holt and the Royal Philharmonic Orchestra, the Annual Caribbean Tourism Week (NYC) and many others. On August 8, 2003, Jamaica's Prime Minister, P.J. Patterson, honored Freddie with the prestigious Jamaican Order of Distinction in recognition of his contribution to Jamaica’s music and culture. His popular tune, Lovers Rock, was featured in the critically acclaimed HBO exclusive Disappearing Acts and Harlem’s famous Apollo Theater saluted Freddie with the honor of being an Apollo Living Legend.