Amy In The Sun: The Other (Caribbean) Side of Amy Winehouse

Words by Jesse Serwer

Amy Winehouse, who died Saturday at age 27, left as her musical legacy a distinctively modern take on the timeless sound of vintage soul music. Lesser known is that the troubled singer was as enamored with Caribbean music as she was with R&B. In fact, her desire to take her followup to Back to Black in a more reggae-leaning direction may have almost as much to do with said album’s failure to materialize as did her well documented drug addiction. Seemingly on the road to recovery, the singer (who had previously indicated plans to record with her friend, Damian Marley) is said to have emerged from several months in St. Lucia in 2009 with a set of dark, heavily reggae-flavored tunes. Ironically, Island Records, the label responsible for turning reggae into a global phenomenon in the 1970s, apparently rejected this material on the grounds that it departed too drastically from the successful Back to Black formula.

While these recordings remain unheard, the influence of the Caribbean can be found across Winehouse’s brief catalog. Salaam Remi, the Bajan-American producer responsible for merging hip-hop with dancehall in the early 1990s, produced the majority of the tracks on her 2003 debut album, Frank, and nearly half of those on Back to Black. Mark Ronson, whose contributions to Back to Black such as “Rehab” and “You Know That I’m No Good” are Winehouse’s signature tunes, gets all of the accolades but Remi probably deserves just as much credit for her blossoming as an artist. On Frank (on which the heavily bossanova-flavored “Know You Now” also featured instrumentation from Jamaican musicians, including guitarist Earl “Chinna” Smith), Remi’s gift for subtly mixing Caribbean elements into non-reggae fare can be heard on a dubby cover of “Moody’s Mood For Love”:

“Just Friends,” one of five tracks Remi produced on Back to Black and the album’s sixth and final single, was more explicit in its island-ness, supporting one of Winehouse’s most understated vocal performances with reggae rimshots and ska-style horns:

Around the time of Back to Black, Winehouse recorded a handful of ska and early reggae covers. Originally released as B-sides to various singles from the album, these were later collected on a bonus disc included in the CD’s deluxe edition and on the limited-run, vinyl-only The Ska EP.  Among these were a version of “Monkey Man,” the 1969 Toots and the Maytals track that has been covered by everyone from The Specials to No Doubt. Performing for over 100,000 fans at England’s Glastonbury Music Festival in 2007, at the height of her popularity, Winehouse closed her set with “Monkey Man”:

Winehouse also covered the Skatalites “You’re Wondering Now” and The Specials’ “Hey Little Rich Girl” and, most interestingly, recorded a one-drop version of Sam Cooke’s “Cupid.” The track follows the template of a 1969 rocksteady version of Cooke’s classic R&B ballad by “I Can See Clearly Now” singer Johnny Nash, the first American performer to record in Jamaica. The arrangement, however, is more basic, emphasizing an astrounding vocal performance from Winehouse in which, despite their anatomical differences, she sounds eerily like Cooke, another singer who died tragically at a young age.

It’s really too early to speculate on the status of any unreleased recordings Winehouse might have made late in her life. Yet it’s hard to imagine that her dalliance with reggae in St. Lucia won’t be something worth looking forward to, should the results ever emerge.