Gary Allan songs are diverse in both subject matter and style.

Over the years, the artist has released sentimental ballads, playful romantic tunes and authentic, raw anthems. His steady career in country music has brought us 11 albums thus far, making him one of the most consistent contemporary artists of the genre.

Allan has earned several No. 1 hits as well as Top 10s, which makes it difficult to narrow down to just a handful of his best tracks, but we put together a list of our frontrunners!

  • 10

    "Tough Little Boys"

    See if I Care (2003)

    Nothing tugs at your heartstrings quite like the universal stages of a parent-child relationship, and "Tough Little Boys" is no exception. In this ballad, Allan explores how nothing is quite as scary or emotional as raising a child, even for tough guys. Fans must have known exactly what he was talking about, because in 2003, the song became Allan’s second No. 1 hit, keeping the singer’s momentum going as one of the leading artists in the genre.

  • 9

    "Best I Ever Had"

    Tough All Over (2005)

    Though "Best I Ever Had" isn’t an Allan original, the country artist brought a new perspective to a well-written alt-rock hit performed first by the band Vertical Horizon. Allan’s personal style lent new life to the somber tune, and it remains one of his most popular tracks. His cover of the song was a Top 10 hit off his 2005 album Tough All Over. It may have seemed like an unusual choice for a country artist to cover such a well-known song from another genre, but Allan clearly knew what he was doing. This is definitely one of the best Gary Allan songs.

  • 8

    "The One"

    Alright Guy (2001)

    This romantic ballad is what every woman wants to hear — a man saying he would do anything for her to be worthy of her. "The One" has a unique a touch of Spanish flare, adding to its whimsical style and charming lyrics. Allan brings a tender approach to the song that the ladies definitely don’t hate, made clear by the song’s peak at No. 3 on the Billboard Hot Country chart in 2002.

  • 7

    "Life Ain't Always Beautiful"

    Tough All Over (2005)

    Allan brings us another bittersweet sentiment with his single "Life Ain’t Always Beautiful." The versatile country music vet walks the listener through the highs and lows of life in the ballad, noting that struggles and disasters will happen, but the journey is still worth it. "Life ain’t always beautiful, but it’s a beautiful ride," he concludes. The song was the second single from Allan’s album Tough All Over and reached No. 5 on the Billboard country charts, proving that the song resonated with fans across the country.

  • 6

    "Watching Airplanes"

    Living Hard (2007)

    A classic story of the one who got away, "Watching Airplanes" is a resignation to reality, accepting that she’s not coming back. "Right now I know you’re 30,000 feet above me, but a million miles away," Allan sings with a little bit of heartbreak in his voice, bringing a level of honesty to the song. Its upbeat, infectious melody is a bit of a juxtaposition considering the song’s lyrics, but perhaps that’s just what we need to balance out the twinge we feel relating to the song. "Watching Airplanes" was a Top 10 hit for Allan in 2007, peaking at No. 2 on the Billboard country charts.

  • 5

    "Man to Man"

    Alright Guy (2001)

    Allan’s first No. 1 hit on the country charts, "Man to Man" paints a scene of a new lover facing his lady's previous suitor, who seems to be causing trouble. Every woman wants a man who will stand up for her, and that’s exactly what this song captures. The catchy tune has a laid-back, almost beachy feel, and fans certainly resonated with it. "Man to Man" was the third single off Allan’s fourth studio album Alright Guy and even peaked at No. 25 on the Billboard Hot 100.

  • 4

    "I Just Got Back From Hell"

    Tough All Over (2005)

    Co-written by Allan in the wake of his wife Angela's suicide in 2004, "I Just Got Back From Hell" is a gut-wrenchingly personal song surrounding his grief over the loss, along with many other songs from his 2005 album Tough All Over. The tune has a bit of a traditional ballad feel — the kind that people used to sing to tell the tales of legends. Allan delivers a passionate performance of the edgy verses and a chorus stained with desperation, an all-encompassing plea to both his late wife and the Lord for forgiveness. While the song was never a hit single, it remains one of Allan’s hidden gems.

  • 3

    "Nothing on But the Radio"

    See if I Care (2003)

    Upon hearing "Nothing on But the Radio" for the first time, listeners soon find out it’s about more than just music. The clever play on words in the title is fitting, given the catchy, lighthearted feel of the love song. The sexy tune was a fan-favorite, becoming Allan’s third No. 1 hit. "Nothing on But the Radio" was the final single off the artist’s fifth album See if I Care in 2004.

  • 2

    "Smoke Rings in the Dark"

    Smoke Rings in the Dark (1999)

    Allan takes on a bit of a Lone Ranger vibe in this ominous tune. "Smoke Rings in the Dark" is a mid-tempo lament of love already lost and a man having to do what he’s got to do by walking away. Released in 1999 on Allan’s third studio album of the same title, the song reached No. 12 on the Billboard Hot Country charts. The song’s unique sound and that dash of edge Allan is known for infusing make it undoubtedly one of his best.

  • 1

    "Every Storm (Runs Out of Rain)"

    Set You Free (2013)

    We all know what it’s like to be fighting an uphill battle at some point in our lives. Allan’s "Every Storm (Runs Out of Rain)" is a hope-filled answer to that gnawing feeling of helplessness. The driving, uptempo track gives just enough beats per minute to propel the listener forward, mirroring the uplifting message, but remains steady enough to keep the somber tone. The catchy chorus and inspirational lyrics earned this song a No. 1 slot on the charts as well as on our list of Gary Allan’s best songs.

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