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Gary Allan's 10 Best Songs: Critic's Picks

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Gary Allan performs at the 37th Annual CMA Awards during 37th Annual CMA Awards at The Grand Ole Opry in Nashville, Tenn. 

Since hitting the Country Music scene in 1996, Gary Allan has developed one of the most dependable careers in the business. He has done so with an attitude that is very much current in sound, yet also hearkens back to some of the great music coming out of Los Angeles and Nashville in the 1960s and 1970s. He’s been the leading man, the tortured poet, and even a doting father in -- and out of his song lyrics.

The selections that made our list of timeless Gary Allan songs are all reflective of each of those descriptions, with each song effectively carving out a spot in the hearts of his fans. Of course, those listeners will likely take issue with some of the songs that aren’t on this list, but the fact is Gary Allan has recorded several songs that deserve to be on this list -- and, that’s what makes the ensuing arguments so enjoyable.

Best Songs: Alabama | Alan Jackson | Blake Shelton | Brad Paisley | Carrie Underwood | Chris Stapleton | Conway Twitty | Cole Swindell | Darius Rucker | Dierks Bentley | Dixie Chicks | Dolly Parton | Eric Church | Faith HillGarth Brooks | George Jones | George Strait | Glen Campbell | Jason Aldean | Johnny Cash | John Denver | Keith Urban | Kenny Chesney | Kenny Rogers | Lady Antebellum | Little Big TownMartina McBride | Merle Haggard | Miranda Lambert | Patsy Cline | Randy Travis | Rascal Flatts | Reba McEntire | Sam Hunt | Shania Twain | Sheryl Crow | Thomas Rhett | Tim McGraw | Toby Keith | Travis Tritt | Vince GillWaylon Jennings | Willie Nelson | Zac Brown Band

10. Gary Allan - "Get Off On The Pain" 

In 2010, the singer hit the Top-20 with this fine effort which represented his more bluesy side. In the song, Allan seemed to revel in the misery he was feeling during the track to great effect. Now, that’s probably unfair to say -- as nobody would admit to enjoying the heartache, but misery in Country Music does sometimes lead to a lot of company!

9. Gary Allan - "Every Storm Runs Out Of Ran"

The most recent Gary Allan song to top the charts successfully compared the roller coaster ride od a relationship to the cycle of a storm. Allan sounded as if he knew every line all too well on this 2012 track that he composed with Hillary Lindsey and Matt Warren.

8. Gary Allan - "Her Man"

Written by the late Kent Robbins, this song that launched Allan's career was originally recorded by one of the singer’s influences, Waylon Jennings, who cut the song on his 1990 album The Eagle. Allan gave the lead character a heartfelt delivery of lyrics that showed a man admitting his weaknesses, yet was simply content just to be with the one he loved.

7. Gary Allan - "Life Ain't Always Beautiful"

This well-written ballad definitely had an artist mentality. One of the co-writers of the song was Cyndi Goodman (Thomson), who topped the charts with "What I Really Meant To Say." The 2006 recording detailed that one’s road in life was not always going to be smooth -- a sentiment he could wholeheartedly identify with.

6. Gary Allan - "Best I Ever Had" 

Vertical Horizon enjoyed the original hit with the song on the Rock charts in 2001, so one might have doubted whether a Country artist could pull such a performance off. Allan did not only that with this cut, but pulled off a dramatic vocal that resulted in his eighth top ten single.

5. Gary Allan - "Man To Man"

In the fall of 2002, Allan notched his very first number one with a song that detailed a heart-to-heart talk between two men – one woman’s ex, and her current lover, as the new guy in town laid out the reasons why he had ever entered the picture in the first place. Allan’s vocal was a little harsh, but it was exactly the reading that the song’s lyrics called for.

4. Gary Allan - "Nothing On But The Radio" 

There are few male vocalists that garner the amount of attention among their female fans as Gary Allan, and this playful 2004 romp still ranks high as one of the sexiest Gary Allan songs the singer has released during his two-decade career.

3. Gary Allan - "Smoke Rings In The Dark"

A lot of Allan’s early work had a definite retro-feel to it, and this song sounded like the perfect mixture of Merle Haggard and Chris Isaak. The vocals and the instrumentation both brought to mind the best music that came from Capitol Studios in Los Angeles, and Allan hammered this one out of the ballpark.

2. Gary Allan - "Tough Little Boys"

Gary Allan has mastered the art of playing the rugged tough guy who nothing gets to in his song choices, but this sentimental track -- which was co-written by the late Harley Allen, shows another side of the singer -- watching as his child is growing up. It was understated, yet also heartfelt at the same time, making for one of his upper-tier performances.

HONORABLE MENTION. Gary Allan - "From Where I’m Sitting"

This 1997 performance is notable for two reasons. While only hitting No. 43 on the chart, it’s one of Allan’s more evocative performances, about a man who is forced to take stock of why he has lost the woman that he truly loves. And, the track from his debut album Used Heart For Salehad a pretty famous name attached to it as a co-writer. Have you ever heard of Garth Brooks? Yeah, we thought so!

1. Gary Allan - "Watching Airplanes" 

As someone who has underwent his share of tough times in life, Allan delivered quite possibly the performance of his career in the summer of 2007 with a song that oozed loneliness and despair. If you could listen to the lyrics of this Gary Allan song and not feel the loss that the singer did, you needed to have your heart checked -- to see if it is beating.