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Jimmy Cliff: Harder They Come

This album is basically a starter kit for fans of traditional reggae and ska. The soundtrack to the film of the movie of the same name, it's often seen as a Jimmy Cliff album, as he was the movie's star, but it's really a compilation soundtrack featuring two artists we'll talk about later (Desmond Dekker, Toots and the Maytals) also features classic singles by the Slickers, Scotty and the Melodians. The movie is also worth a watch—Cliff stars as a poor man who, after recording the title track, gets bilked by his producer, ends up dealing marijuana and then becomes a famous criminal leading police on a manhunt. It's a good intro to Jamaican rude boy culture, their admiration for American Westerns and their slang, although you'll probably need subtitles to understand a lot of it. The film studio even included them during the initial theatrical release because the lingo is so tough for many English speakers.

Prince Buster: Fabulous Greatest Hits

Prince Buster got his start running his own sound system, a part of Jamaican culture where DJs, engineers, MCs, promoters, etc. would blare music at street parties and compete to have the freshest exclusives. Unable to keep up with his rivals' collections, Buster decided to just record some new tunes himself, either singing, scatting or toasting over instrumentals. On this 1968 compilation, you'll find heartfelt rocksteady crooning with "Julie," but mostly you'll hear him chatting over some gorgeously lo-fi instrumentals, or basically doing a proto-rap sketch on "Judge Dread," where he sentences a rude boy to 400 years in prison for shooting black people. In terms of social commentary, it's almost the opposite of "Ten Commandments," a (hopefully) tongue-in-cheek sermon directed at all the women in his life to let him get away with anything while they remain faithful. He became a huge inspiration for 2 Tone bands: Madness took their name from one of his songs, and The Specials and The Beat also covered some of his tracks.

The Skatalites: Ska Authentic

The Skatalites are ska's equivalent to supergroups like Motown's Funk Brothers and L.A.'s Wrecking Crew, except they were—and still are—the band whose name goes on the marquee, even though every founding member except alto sax player Lester Sterling has since passed away. Mainly jazz players, the group started loosely in the '50s and were brought together in the '60s by producer and Studio One fonder Clement "Coxsonne" Dodd. While best known for their take on the instrumental "Guns of Navarone," they also served as the studio band for tracks by Marley and the Wailers, Prince Buster, Lee "Scratch" Perry and many more. Ska Authentic, their 1964 debut, is the perfect place to start appreciating them, and getting to know the influence members like Tommy McCook, Roland Alphonso, Don Drummond, Lloyd Brevett and Lloyd Knibb had on generations to come.

The Wailers: The Wailing Wailers

The ska vocal group formed in 1963 with Marley, Peter Tosh and Bunny Wailer wore suits and shorter hair, as opposed to the military fatigues and dreads they'd don later as reggae artists. Released in 1965 by Studio One with Dodd producing, The Wailing Wailers features Bob sounding more like a lower-pitched Frankie Lymon. There's the earliest rendition of "One Love," a cover of "What's New Pussycat?" and the album's closer, "Simmer Down," Marley's plea for peace among the young gang members in the Kingston ghettoes. It was his first No. 1 hit.

Toots and the Maytals: Funky Kingston

Led by the soulful voice of Toots Hibbert, the Maytals' 1968 song "Do the Reggay" was the first track to use the term that defined the genre. There are plenty of great Toots tunes, but a good starting place is Funky Kingston, with this version being a 1975 U.S. repackaging of an earlier album to bring some of the band's best work to the American audience as reggae was starting to become popular. There are covers of "Louie, Louie" and John Denver's "Country Road," and one of his signature songs, "Pressure Drop," which was featured on The Harder They Come and later famously covered by the Clash. Simply put, Toots is a force of nature on the mic, and this is the perfect way to get to know him more and then explore the rest of his discography. As of this year, he's back on the road following a hiatus due to a head injury he suffered when a fan threw a bottle of vodka at him. Get out and see him if you can.

Desmond Dekker: The Israelites

In 1964, Desmond Dekker proclaimed himself the "King of Ska" in a single backed by the Maytals, and we're not going to argue with that title, though he later became royalty in rocksteady and reggae. If you have The Harder They Come, you already have his hit "007 (Shanty Town)" so next up we'd recommend Israelites, a reissue of the crooner's 1969 UK album, which features some of his greatest hits: "Israelites," "It Mek" and "Rude Boy Train." As a friend related in the email announcing the birth of his son, Desmond, Dekker was the inspiration for the Desmond in the Beatles' "Ob-La-Di, Ob-La-Da," was name-checked in Rancid's "Roots Radicals" and was given a posthumous tribute from the Mighty Mighty Bosstones on " Don't Worry Desmond Dekker."

Laurel Aitken: The Fantastic Laurel Aitken

While Desmond is the King of Ska, Laurel Aitken is the Godfather. In the late '50s, the Cuban native worked with Island Records founder Chris Blackwell, and released a number of singles in England in the '60s, leading to a rise in popularity of the genre there. He was so prolific that it's difficult to really find a vinyl record that encapsulates his career, but The Fantastic Lauren Aitken, a reissue of a 1970 rarity, helps illustrate the beauty in his voice, his tenderness and sometimes vulgar lust, and how he helped ska and reggae move forward, especially with his popularity in Britain and influence on the 2 Tone movement.

Bob and Marcia: Young, Gifted and Black

The biggest outlier on this list, Bob Andy and Marcia Griffiths' 1970 collaboration blends reggae with some contemporary American soul influences, like orchestral arrangements. Think a Jamaican version of Marvin Gaye and Tammi Terrell, with production like Dusty in Memphis. Both singers had individual success as solo artists and as members of other groups: Andy was in the Paragons, best known for their Blondie-covered hit "The Tide Is High," and Griffiths as one of the I Threes, the trio of female backing vocalists who joined Bob Marley and the Wailers after Peter Tosh and Bunny Wailer departed.

Derrick Morgan: Shake A Leg

Another ska pioneer, Derrick Morgan once had the honor of having his singles chart in the top seven spots in Jamaica. This album collects some of his earlier tracks, including "Be Still," "The Hop," the Patsy Todd duet "Housewives Choice," and "Forward March," which celebrated Jamaica's 1962 independence from the U.K. A rival of Prince Buster's, he worked with Marley, Dekker and Cliff, helped pioneer rocksteady with "Tougher Than Tough" and reggae with "Seven Letters," and even influenced British skinheads with "Moon Hop," which was covered by the non-racist group Symarip and released as "Skinhead MoonStomp." Now 76 and blind, Morgan still makes occasional live performances.

The Upsetters: Blackboard Jungle Dub

The Upsetters, the house band of producer Lee "Scratch" Perry, debuted with their own album Return of Django in 1969 and backed Bob Marley on some of his early reggae recordings. But it was this 1973 album that had a huge influence on the reggae world and its followers, as it's one of the first examples of dub, the subgenre that features an emphasis on bass and drums, heavily reverbed sounds, instruments that appear and disappear from the mix, and all sorts of random warbles and effects. Once you get into this, move backward to Django and forward to 1976's Super Ape.

Augustus Pablo and King Tubby: King Tubby Meets Rockers Uptown

After praising Perry's contributions to dub, it'd be a sin to not include King Tubby Meets Rockers Uptown, the 1976 collaboration between genre pioneer Tubby and producer/instrumentalist Augustus Pablo. Held down by the bass and drums of Wailers' rhythm section Aston and Carlton Barrett, Tubby's mixing and Pablo's playing, specifically on the melodica, still sound ahead of their time.