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Bob Dylan and The Band go a long way toward defining the complex musical genre known as Americana.

Clint Austin/AP

With Bob Dylan, Wilco, My Morning Jacket and Richard Thompson fixing to set up tent for their rolling Americanarama Festival in Toronto on Monday, a question is raised: What is Americana music? The Americana Music Association, for one, defines the genre so: "Contemporary music that incorporates elements of various American roots music styles, including country, roots-rock, folk, bluegrass, R&B and blues, resulting in a distinctive roots-oriented sound that lives in a world apart from the pure forms of the genres upon which it may draw. While acoustic instruments are often present and vital, Americana also often uses a full electric band."

Which is a mouthful, but loosely translates as "Dylan."

Often, when seeking answers to life's tougher questions, we turn to song. With that in mind, here are five tunes that represent (and perhaps define) Americana music:

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Boulder to Birmingham by Emmylou Harris and Bill DanoffIt is more than 2,100 kilometres from Boulder, Colo., to Birmingham, Ala., but the best route is less than four minutes long, as heard on Harris's 1975 album Pieces of the Sky. It has been said that the achingly sweet lament was written in memory of Gram Parsons, a singer-songwriter and Americana pioneer.

She, by Gram Parsons and Chris Ethridge

A third-person-singular ballad salutes the power and pleasure of the crooning human voice, particularly one possessed by a woman born in the "land of the cotton." The version recorded by Parsons for his initial solo album, GP, is notable for its soft swing and serenely played pedal-steel guitar – an instrument that sure can sing, to paraphrase Parsons.

Copperhead Road, by Steve Earle

The power-twang side of Americana, with an intergenerational story that moves from moonshining to the Vietnam War to backwoods drug running. Which is as Americana as whistlin' Dixie.

Up on Cripple Creek, by Robbie Robertson

You can't spell Americana without more than one "eh." Four Canadians and one drawling Arkansan, together known simply and definitively as The Band, helped invent roots-rock. Here, against a funky Clavinet soundtrack, Levon Helm sings of gambling, drinking and a woman named Bessie who is "a drunkard's dream if I ever did see one."

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Blind Willie McTell, by Bob Dylan

If nobody could sing the blues like Blind Willie McTell (a lens-uncorrected ragtime songster particularly troubled by "those Statesboro blues"), nobody could write an homage like Dylan. On a simply strummed stunner melodically similar to the traditional St. James Infirmary Blues, a portrait of the Deep South and its sounds, scents and slavery is told – "Hear the cracking of the whips, smell that sweet magnolia blooming."

Americanarama Festival of Music, July 15, Molson Amphitheatre, ticketmaster.com

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