It is interesting to note that the pop calypso (as opposed to real calypso) boom of the mid 1950s was engineered largely by a charismatic singer born in Harlem and a Julliard trained composer from Brooklyn. Both Harry Belafonte, whose mother was from Jamaica, and Irving Burgie, who spent his childhood in a West Indies neighborhood in New York, had musical roots in the Caribbean, certainly, but their version of the islands was largely an imagined one, although imagined so well that their collaborations have actually filtered back into the folk music of the region.

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Elizabeth Cotten’s “Shake Sugaree” is a delightfully whimsical song that carries at its heart a good deal of wisdom. Cotten developed the simple melody of the song from folk sources, and used it as a lullaby when putting her great grandchildren to bed in the evening. She encouraged the kids to think of words for the song, and they all had a hand in its composition. The song seems to be about hardship and poverty, as the lyrics list all manner of things that the singer has pawned, but the chorus (“didn’t we shake sugaree”) is upbeat and bears no trace of regret. To “shake sugaree” is to dance. Jean Ritchie has suggested that “sugaree” is a reference to the Appalachian practice of “sugaring,” of throwing sugar out to “slick up the dance floor.” So the message in “Shake Sugaree” seems to be that no matter how bad things get, you can always dance. Cotten’s original version was the title tune on her second album for Smithsonian Folkways, and the lyric was actually sung by one of her great grandchildren, Brenda Evans, who was then only 12 years old. Cotten performed the song frequently in concert, and its lightly surreal lyrics and gentle, positive tone have made it a popular cover song in folk circles. Taj Mahal, Mary Lou Lord (with Elliot Smith on guitar), Chris Smither, Greg Brown, Faith Nolan, and Po Girl have all recorded versions of “Shake Sugaree.” Fred Neil covered it as “I’ve Got a Secret (Shake Sugaree),” and it is Neil’s rendition that Bob Dylan used when he performed the song on his 1996 and 1997 tours. The Grateful Dead song “Sugaree” is based on Cotten’s original, but is essentially an entirely new piece, in which Sugaree becomes the name of a woman (a hooker, actually). Aside from “Freight Train,” “Shake Sugaree” is Libba Cotten’s best-known song, and its timeless and gentle wisdom make it a wonderfully joyous lullaby, one that feels like it has always been there.

Former Hot Damn Jammers Free Energy made a video for their incredible summery new single on DFA called “Free Energy,” and we think you should watch it. Their freewheeling ’70s sound is an amalgamation of all the great easygoing, good time rockers like Tom Petty, Steve Miller, Joe Walsh and Cheap Trick, with a bunch of power pop sweetness thrown in to keep things from getting too heavy. The video makes being in a rock band in the city in the summertime look like just about the coolest thing possible.

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For everybody who decries the state of contemporary pop music as a vast wasteland of disposable, commercial junk, and for anyone who longs for the days when composers like George Gershwin, Harold Arlen, Cole Porter, Irving Berlin, and Hoagy Carmichael wrote beautifully crafted songs with hummable melodies and clever, story-based lyrics with real characters in them, I present to you the soundtrack to the film Synecdoche, New York.

Featuring music by journeyman producer/songwriter/multi-instrumentalist and Los Angeles man-about-town Jon Brion, the soundtrack also showcases two tracks — “Little Person” and “Song for Caden” — co-written by Brion and the film’s director Charlie Kaufman, sung by jazz vocalist Deanna Storey. Both of these songs are superbly crafted tunes in the tradition of the American Popular Songbook style as well as being reminiscent of the storied ’60s Brill Building sound of writers like Carole King and Burt Bacharach. Furthermore, Storey’s georgeous, subtly emotive voice brings to mind a young Barbra Streisand, who herself made a mark with such Broadway soundtrack hits as “People” from the musical Funny Girl.

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Perhaps sensing that moving on was a predominate American response to solving a whole host of life’s problems, and recognizing that the long haul trucker was a close cousin to the river boat gambler, Dave Dudley shrewdly grafted reverb-heavy Telecasters to a slowed down rockabilly rhythm and almost single handedly invented the truck driving subgenre of county in the early 1960s. He would stretch the long lonely road metaphor from Nashville to Bakersfield in such classic trucking songs as “Truck Drivin’ Son-of-a-Gun,” “There Ain’t No Easy Run,” and the decidedly un-PC “Two Six Packs Away.” With his deep, workingman’s voice, Dudley made a kind of cowboy poetry out of the nomadic lifestyle of truckers, and lines like “The highway is a part of hell that never caught fire” from the Tom T. Hall-penned “Listen Betty (I’m Singing Your Song)” give his best recordings a timeless shelf life — unless, of course, America ever falls out of love with motion. Which isn’t likely. So that means that Dudley’s “Six Days on the Road,” probably the greatest trucking song ever written, will continue to be relevant as long as there’s an Interstate Highway System and the need for a six day work week. It’ll stay relevant even beyond that. It’s a song about coming home.

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The Uniques’ “Watch This Sound� is based on a mishearing (either by accident or on purpose) of a Stephen Stills song recorded by Stills’ group Buffalo Springfield called “For What It’s Worth.� Stills had written the song after observing a heated encounter between kids and police outside Pandora’s Box, a teen rock club on L.A.’s famed Sunset Strip, in 1966. The club, one of the few in the area that opened its doors to kids under the age of 18, was slated to be torn down for a road- widening project, and when the LAPD instituted a tight 10 p.m. curfew for minors, an impromptu protest outside Pandora’s Box began, leading to the confrontation that Stills details in his song. “For What It’s Worth� became the debut single for Buffalo Springfield, hitting the charts in 1967. Meanwhile, back in Jamaica, the second incarnation of the Uniques (the first version of the vocal trio had included Slim Smith, Roy Shirley and Franklyn White) with Slim Smith, Jimmy Riley and Lloyd Charmers was just taking shape, and they eventually came up with an arrangement of the Stills tune, hearing the original chorus of “stop, children/what’s that sound/everybody look/what’s going down� as “stop, children/watch this sound/everybody look/what’s going on.�

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In 1965 a striking single called “New York’s a Lonely Town” by a group called the Trade Winds flitted briefly across pop radio. Telling the story of a California surfer stuck in New York for the winter, the song was beautifully produced, echoing some of the studio techniques then favored by Brian Wilson, and although the song’s premise seems even more ridiculous now than it did then, “New York’s a Lonely Town” has such a memorable, lilting melody and projects such willful yearning and innocence that it is somewhat of a lost pop treasure.

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It is interesting to note that the pop calypso (as opposed to real calypso) boom of the mid 1950s was engineered largely by a charismatic singer born in Harlem and a Julliard-trained composer from Brooklyn. Both Harry Belafonte, whose mother was from Jamaica, and Irving Burgie, who spent his childhood in a West Indies neighborhood in New York, had musical roots in the Caribbean, certainly, but their version of the islands was largely an imagined one, although imagined so well that their collaborations have actually filtered back into the folk music of the region. Intelligent, confident, and with a firm grasp of artful arrangement, Belafonte almost single-handedly brought world music into the commercial pop arena with the Burgie-composed “Day-O” song, and in Burgie he had found the perfect songwriter, a man whose compositions had the lilt and flow of ocean sunlight. Several of Burgie’s songs (and Belafonte’s versions of them) have become stone cold classics, including “Banana Boat (Day-O),” the lovely “Jamaica Farewell” (both of which were centerpieces of 1956’s million-selling Calypso album that made Belafonte an international star), and the joyful “Kingston Market.” Calypso from Jamaica contains all the tracks from that ground-breaking release plus related tracks from Belafonte’s subsequent RCA albums to make a wonderful sequence of artful, faux Caribbean folk that isn’t particularly Jamaican, although it definitely is shot through with a West Indies sensibility. The only actual folk song from the Caribbean included on the album is the gorgeous 19th Century ballad “All My Trials,” which by the 1950s had migrated to the American south and by the 1960s had become a staple of the Folk Revival. Whatever the origins, the songs collected on Calypso from Jamaica have a wonderfully summery vibe, and if most of them didn’t actually come from the Caribbean, they certainly ended up there, and many of these tunes have become mento standards. Calypso from Jamaica is the most generous single disc currently available of this phase of Belafonte’s career.