When Dierks Bentley crashed into the country music scene with his eponymous debut album on Aug. 19, 2003, he brought a youthful and mischievous energy that stood in contrast to the heavy-hitters of the moment. In the genre's rich, booming culture of early 2000s, dominated by talents such as Toby Keith and Brooks & Dunn, Bentley found himself rising to the surface with his debut single, "What Was I Thinkin'," his first No. 1, that gave everybody a run for their money.

Right out of the gate, the curly haired Arizona native was a force to be reckoned with, and after nearly two decades, he still is. Bentley is a writer on 11 of the 13 track on his self-titled debut album; from the rowdy single "How Am I Doin'" to the somber reflection "My Last Name," Bentley gave fans a taste of his talent and versatility from the very beginning, offering up bittersweet ballads and heel-stomping tunes.

To celebrate the 16-year anniversary of the release of Dierks Bentley, The Boot has ranked each of the album's tracks, down to the top single off the album that launched the artist into country stardom. Read on to see how they all stack up.

  • 13

    "I Bought the Shoes"

    A honky-tonk ballad for the ages, "I Bought the Shoes" is one of only two tracks on Dierks Bentley that Bentley didn't have a hand in composing. Written by Jimmy Melton, Dale Dodson and Ken Mellons, the country swing tune falls right in line with Bentley's diverse collection of throwback sounds.

  • 12

    "Forget About You"

    Track No. 3 on Dierks Bentley is an introduction to the moving-on attitude that Bentley would go on to perfect in later hits such as "Drunk on a Plane" and "Somewhere on a Beach." With its classic sound, "Forget About You" gave Bentley solid country cred right out of the gate.

  • 11

    "Wish It Would Break"

    The second track on Bentley's debut album is a bittersweet ode to lost love and the hope that all of the reminders surrounding the brokenhearted singer will somehow go away. This song is the first taste of Bentley's bluegrass stylings and the heartache his voice so deftly captures.

  • 10

    "I Can Only Think of One"

    Bentley's storytelling gift shines in "I Can Only Think of One," a song that follows the singer as he paints a picture along the winding road of memories.

  • 9

    "Train Travelin'"

    Bentley's bluegrass influences also shine through in the traditional sound of "Train Travelin'." Written by Bentley, the song features the legendary Del McCoury Band backing the singer.

  • 8

    "Distant Shore"

    Bentley's heart-wrenching vocals lend emotion to this farewell tune. Far East sounds flow into the melody of loss and bidding a loved one goodbye.

  • 7

    "Whiskey Tears"

    This classic heartbreak tune was included on Bentley's independently released album from before he signed with Capitol Nashville, but he re-recorded it for his major-label debut.

  • 6

    "Is Anybody Loving You These Days"

    Bentley gets a little bit '90s country in Dierks Bentley's flirty seventh track. Feel-good pop vibes shine through the upbeat melody, another glimpse of the artist's versatility in both songwriting and delivery.

  • 5

    "My Love Will Follow You"

    A soaring ballad of romantic promise, "My Love Will Follow You" was the first of many love songs that Bentley offered his fans.

  • 4

    "Bartenders, Etc. ..."

    From its sound to its title, "Bartenders, Etc. ..." has Dwight Yoakam's influence all over it. The song is also included on Bentley's previously released independent album, and it's the only track on his major-label debut that he wrote alone.

  • 3

    "My Last Name"

    This track was one of three singles from Bentley's debut album, and it notched its way up into the Top 20 on the country charts in 2003. A major turn of mood and sound from Dierks Bentley's first and third singles, "My Last Name" is a demonstration of the artist's depth and versatility.

  • 2

    "How Am I Doin'"

    Bentley tears it up in "How Am I Doin'," in keeping with how he launched his career. This track is the third single from his debut album, and it raced its way up the charts to No. 4. It's a fan favorite at live shows to this day.

  • 1

    "What Was I Thinkin'"

    The wild-eyed romp that started it all, "What Was I Thinkin'" was Bentley's introduction to the country music world -- and what an impression it made. While making its way to the top of the charts it was the perfect showcase of the singer's talent, sense of humor and relatable, rowdy country-boy style.