10 Essential Gary Allan Songs

When it comes to renaissance men in country music, no list would be complete without Gary Allan on it. Known as much for his rugged good looks as he is for his string of country hits, Gary is also intelligent, articulate, gentle, gracious, kind and downright funny. He’s also an entrepreneur, previously showcasing his incredible flair for style with his Nashville clothing store, The Label, and through his unique line of homemade jewelry. His interests and talents are as diverse as his cross-genre appeal.

If you are new to the world of Gary Allan, we have 10 suggestions to get you up-to-speed with the magic of his music.

(Arranged chronologically)

“Lovin’ You Against My Will” from Smoke Rings in the Dark
Written by: Jamie O’Hara
This song was our mainstream introduction to all of the moody goodness that is Gary Allan. Half outlaw, half GQ model, he also made it abundantly clear that he would be making as significant a contribution the California country music scene just as Buck Owens and Merle Haggard did.

“Right Where I Need to Be” from Smoke Rings in the Dark
Written by: Casey Beathard, Kendell Marvel
Gary’s second single, “Right Where I Need to Be,” put him on the map with his first Top 5, but also reinforced his commitment to country music with soaring fiddle in his arrangement. It also inched him over from just being another hot country star to being a bona fide sex symbol.

“The One” from Alright Guy
Written by: Karen Manno, Billy Lee
So, that whole sex symbol thing? If country music fans hadn’t realized it yet, “The One” certainly would have pushed them over the edge. A dreamy ballad filled with the great texture of Gary’s gritty voice, this could have easily been the engagement anthem of 2002.

“Tough Little Boys” from See If I Care
Written by: Don Sampson, Harley Allen
Everything about “Tough Little Boys” screamed that Gary Allan was a country star. Rippling fiddle, moaning steel and lyrics that any daddy could relate to, this, his second No. 1 hit held that favorite male country theme that George Strait’s “Love Without End, Amen,” shared. That as tough as our cowboys are, they have hearts of gold.

“Songs About Rain” from See If I Care
Written by: Pat McLaughlin, Liz Rose
We don’t hear a lot of big, waltz-y ballads in mainstream country music. They seem to be born from Texas artists more often, but Gary wasn’t scared when he released “Songs About Rain,” a true homage to traditional country. Between name-checking every song about rain and retro production, it’s so fun to sing along to.

“Nothing On but the Radio” from See If I Care
Written by: Byron Hill, Brice Long, Odie Blackmon
Gary earned quite the reputation for being brooding and moody, but it was mostly based on his dark appearance and piercing eyes. In reality, he’s a cowboy surfer and his 2004 smash, “Nothing On but the Radio” showed he had as much a knack for a fun, breezy number as he did for more introspective tunes.

“Best I Ever Had” from Tough All Over
Written by: Matt Scannell
This was a tough one for fans of Gary Allan. After his wife of there years, Angela, committed suicide. “Best I Ever Had” was the first single released from his fourth album and was a cover of a Vertical Horizon hit. It seemed to be a message to his fans asking for their patience while he dealt with the incredible loss with lines like, “It might take some time to patch me up inside, but I can’t take it so I’ll run away and hide.”

“Life Ain’t Always Beautiful” from Tough All Over
Written by: Cyndi Goodman, Tommy Lee James
Gary has often said that he sings songs about where he is in his life at that moment and this 2006 Top 5 is evidence of that. Just over a year after the suicide of his wife, Gary had gained some perspective and, even though he didn’t pen this incredible anthem, it seemed as relevant to his life as anything in his catalog.

“Learning How to Bend” from Living Hard
Written by: Gary Allan, James LeBlanc, Matt Warren
With “Learning How to Bend,” Gary was once again addressing his real life, but this time he dug even deeper and co-wrote the song. In addition to seeing him evolve as a songwriter, we also started to feel the gradual evolution Gary was making with his sound with bigger arrangements and crisp production.

“Hangover Tonight” from TBD
Written by: Gary Allan, Chris Stapleton, Cary Barlowe, Jesse Frasure
It’s hard to find someone that can sing a heartbreak like Gary does. The raggedness of his voice lends itself beautifully to that kind of ache and draws us right in buy the next round of tequila. But he reminded us of his awesome diversity with the fun “Hangover Tonight.” He also reminded us of how much respect he has for the artists that came before with a fun, vintage arrangement.