Top 40 Smash Near Misses — “Whiskey Lullaby”

These posts are about the songs that just barely failed to cross the key line of chart success, entering the Billboard Top 40. Every song featured in this series peaked at number 41.


In the late nineteen-nineties and into the early two-thousands, there was a lot of room for country music on the pop charts. Led by the likes of Faith Hill and Shania Twain, multiple artists crossed over from the twangier slices of the radio dial, perhaps reflecting a recognition that as broadcasters were losing their hold on the mass listenership, country fans were uncommonly devoted. Even so, the tracks that did best, perhaps understandably, were often those that wore the Nashville influence lightly. The more country an artist was, the less likely they were to ascend particularly high on Billboard‘s main chart.

Brad Paisley is — and established himself almost immediately as — one of the biggest country music performers of his generation. Paisley’s second single, “He Didn’t Have to Be,” topped the country music chart, and he would return to that peak often. At one point, Paisley claimed the chart’s top spot with ten straight singles. Once that streak ended, his next seven singles made it to at least the runner-up slot, with four of those landing at #1. Of those seventeen songs, only one made into the Billboard pop Top 20, and that had the boost of Carrie Underwood sharing vocal duties. By my rough count, Paisley made it into the Top 40 seventeen times, almost always stalling out low enough that the songs still felt more like also-rans than big hits.

And then there’s the song that sputtered and started to drop after peaking just outside the Top 40. As might be expected, the cut in question is very, very country. Penned by Jon Randall and Bill Anderson, “Whiskey Lullaby” is almost country music cliche, recounting a tale of woe that includes a man who drinks himself to death over heartbreak (“We watched him drink his pain away a little at a time/ But he never could get drunk enough to get her off his mind”). Then the woman who left him commits the same grueling suicide by constant inebriation because of the guilt she feels at her ex-lover’s demise.

Even for country music, “Whiskey Lullaby” is grim stuff, which is why it sat unclaimed for around five years before Paisley took it on. Paisley decided that it would work better as a duet and recruited Alison Krauss as a partner. Released as the third single from the album Mud on the Tires, the song was a major hit on country radio, reaching #3 on the relevant chart, earning double platinum certification by the RIAA, and weighing down the shelves of both Paisley and Krauss with country music awards.

Other entries in this series can be found by clicking on the “Top 40 Smash Near Misses” tag.

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