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No one really knows what “alternative country” means, but it is clearly a wide enough umbrella to cover a flower grower from Massachusetts, a Canadian who grew up farming and a Texas troubadour.

The combination of all three on the same show, billed as a night of “alternative country at its fiercest,” proved magical at times Friday night at the Park West.

Robert Earl Keen, the Texan who headlined, has his share of songs that attract half-drunk revelers who sing along in complete oblivion to the meaning of his lyrics. And while Keen could devolve into the background musician for an endless frat party, he is so good at detailing the lives and dreams of losers and drifters, here’s hoping he continues to nurture his gift as a songwriter.

Keen and his deft band satisfied the crowd with a mixture of older songs and several from his latest album, “Picnic.” They began to kick it into overdrive about midway through the set, reaching a rocking high point with “Shades of Gray,” about three dumb, drunk and stoned young men who go from bad to worse and live to tell the tale after the police decide they’re too “sorry” to be criminals. Like the best of Keen’s songs, “Shades of Gray” is full of delicious details, such as the fact that the song’s two brothers were kicked out of high school “for pushing over port-a-cans at the 4-H rodeo.”

The encore, nearly four hours after Cheri Knight opened the show, was one of its sweetest moments. Keen and the band turned off the sound system and did a gentle acoustic version of Billy Joe Shaver’s “(I’m Going to) Live Forever.” It would not have been possible in a hall any larger than the Park West and was probably what the Old Town School of Folk Music had in mind when it first booked the show for its own intimate hall.

Like Keen, Canadian Fred Eaglesmith both mocks country music’s conventions and honors its roots. Eaglesmith is a raw-voiced singer and powerful performer whose fascination with guns, trains and fast cars played itself out in a rush of songs full of smart writing that belied his attempts to portray himself as the songwriter of choice for “the mobile home community.”

And while he had the audience laughing with songs that glorified big hair and asked, “When exactly did we become white trash?” Eaglesmith’s more serious songs, especially “Wilder Than Her” and the bluegrass-flecked “Thirty Years of Farming,” were the ones that soared. He and his band had much of the crowd on its feet by the end of a gripping set that would have overshadowed a lesser talent than Keen.

Knight, the flower grower from Massachusetts, opened the evening with several fine songs from “The Northeast Kingdom,” a relatively undiscovered gem that stands with the year’s best albums. Her voice occasionally got lost in the mix, especially on the louder, more rock-oriented songs, a problem that at times plagued Eaglesmith and Keen as well. Still, Knight’s sweetly evocative “All Blue” and the plaintive, pedal-steel-driven “Crawling” seemed to linger long after the music stopped for the night.