Gary Allan's Most Heart-Wrenchingly Sad Songs

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Country superstar Gary Allan has been a hit-making machine for damn-near two decades now. The 46-year-old California native has finely walked the line between stadium filler and perpetual critical favorite with little following.

Due to the tragedy surrounding the 2004 suicide of his third wife, Angela, he became an even more compelling figure. While he didn't seek out the extra attention that came from such horrific personal turmoil, the albums in the aftermath of such heartbreak took on extra meaning whether he wanted them to or not. In light of those circumstances, even the relatively schlocky "Best I Ever Had," a cover of the mom-rock group Vertical Herizon's 2001 hit song, became a powerful statement.

Darkness in some form or another has been something Allan has dealt heavily in before the loss of Angela, though. In his earliest days of recording on a large scale, Allan regularly sang with a sadness that he barely kept hidden. Sometimes the darkness was hit-you-over-the-head obvious, and while at other times much less so. Allan's even used darkness as a tool instead of a thematic feeling or vibe.

Allan brings his truckload of hits -- including some happily sunny ones, such as "Watching Airplanes," "Nothing on But the Radio" and "She's So California" -- to Billy Bob's Texas in Fort Worth on Saturday night. To mark the occasion, here's some of his darker material, both obvious and less than such.

5. "It Would Be You"

Storms and rough weather pop up in many of Allan's best songs and those are certainly dark as well. Here, in one of his very first radio hits, he sings in order to properly detail the depth of his pain. (That would make for a long sad song, and a really strong, stiff drink.) Talk of his heartache gets dark, however, when he sings, "If it was a color, it would be deep, deep blue." Deep is dark.

4. "Drinkin' Dark Whiskey"

From his 2003 album,

See If I Care

, this is a fantastically stone-cold country tune written by the still under-appreciated Chris Stapleton. No, this isn't about death or the most guttural aspects of the human condition, but too much "dark whiskey" has a way of bringing out the worst in most of us. Here, Allan admits to "telling white lies" when he starts sipping. Of course, he also sings, "Don't cross your heart unless you hope to die." So that's a bit macabre, no?

3. "Every Storm (Runs Out of Rain)"

In his vast collection of great tunes, let alone the ones that have managed to become hits, this slick single from Allan's latest album,

Set You Free

, isn't in a battle to become one of his signature tunes. But it is a sneakier sad song than one would glean upon a cursory listen. With the help of co-writer Hillary Lindsey's vocals, which are every bit as aching as Allan's are, it becomes clear the couple in question is in danger of splitting still, and the hope that their "dark night turns into day," may or may not ever actually happen. Indeed, the song's pop arrangement lends itself to a positive vibe, but like we said, this is a sneaky one.

2. "Smoke Rings in the Dark"

Arguably Allan's greatest tune, this moody, western 1999 hit single helped Allan create a unique, personal spot in the always-shrinking corporate radio playlists. But we want to discuss darkness, right? In the tune's key passage, a rather gloomy Allan sings, "The night is like a dagger/Long and cold and sharp/As I sit here on the front steps/Blowing smoke rings in the dark."

1. "I Just Got Back From Hell"

There's no getting around it. The loss of a dear loved one due to suicide is as dark as life can get for those of us still above ground. In a rare, raw, powerful display of vulnerability within the country music mainstream, Allan got real in 2005 with this stunning song after his wife's suicide. It would be a few more years before he would address the tragedy publicly, except for when he played this song live, which seems to say it all. In unflinching fashion, Allan sings, "And I guess to tell the truth/Well, I've been mad at everyone/Including God and you." He then divulges his readiness to accept any role he may have had in the tragedy, singing, "Forgive me if I had any part/If I ever broke your heart in two/Forgive me for what I didn't know/For what I didn't say or do."

GARY ALLAN performs Saturday July 12 at Billy Bob's Texas in Fort Worth. Tickets start at $20.00 and can be purchased at www.billybobstexas.com

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