With 25 studio albums released, 26 career Billboard Hot Country No. 1 singles, and over 150 major music industry awards to date, not many artists can beat the illustrious career of country superstar, Alan Jackson.

Launching into the scene in 1989 with “Blue Blooded Woman” off his debut album Here in the Real World, it wasn’t until the release of his song “I’d Love You All Over Again” that his chart-topping career began. Since then, the Newnan, Ga. native’s music has transcended generations. With enduring classics like “Chattahoochee,” “Livin’ On Love,” “Drive” and “Remember When,” country fans both young and old have connected with his music.

However, when looking back at his career, not all fan favorites peaked at the top of the Billboard Hot Country Songs chart. For example, the chill-sending Hank Williams tribute “Midnight in Montgomery” and inspiring “Chasin’ that Neon Rainbow” peaked at No. 3 and No. 2 respectively. Still, notching 26 No. 1’s is no easy feat and achievement.

A well-respected, beloved and highly successful artist in the country format, Jackson’s laudable achievements have surpassed the boundaries of the music charts. He’s a member of the Grand Ole Opry, Country Music Hall of Fame, and Songwriters Hall of Fame, and has attained 19 Academy of Country Music Awards, 16 Country Music Association awards, and a pair of Grammys, amongst others. The singer even has his own four-storey bar and music venue, AJ’s Good Time Bar, situated in the heart of downtown Nashville.

Set to kick off his Last Call: One More for the Road Tour this summer, The Boot looks back on and ranks all of Jackson’s chart-toppers. Keeping reading to out where your favorite song comes in on our list!

  • 26

    "As She's Walking Away" (with Zac Brown Band)

    From: '34 Number Ones' (2010)

    Also serving as the lead single from Zac Brown Band’s sophomore album You Get What You Give, this Jackson-assisted tune snagged a win for Best Country Collaboration with Vocals at the 53rd Grammy Awards in 2011.

  • 25

    "Someday"

    From: 'Don't Rock the Jukebox' (1991)

    Plain and simple, this ballad broods the painful consequences one’s from empty promises. It was co-written by Jackson and Jim McBride and was the second No. 1 single from the Jackson’s Don’t Rock the Jukebox record.

  • 24

    "Good Time"

    From: 'Good Time' (2008)

    Self-penned by Jackson, this was the title track and second single off Jackson’s fifteenth studio album. Its line dance-themed music video even featured cameo appearances from the late George Jones and his wife Nancy.

  • 23

    "Love's Got a Hold on You"

    From: 'Don't Rock the Jukebox' (1991)

    This jaunty and fun tune was the only track that Jackson didn’t write on his multi-award-winning sophomore record, Don’t Rock the Jukebox.

  • 22

    "Dallas"

    From: 'Don't Rock the Jukebox' (1991)

    In this mid-tempo song, a forlorn Jackson helplessly ponders on an ex named Dallas who’s up and left him for a future in the same-named Texas city.

  • 21

    "I'd Love You All Over Again"

    From: 'Here in the Real World' (1990)

    Solely penned by Jackson, this song was dedicated to his high school sweetheart and wife, Denise. The pair met at Newnan High School in Georgia and eventually wed in 1979.

  • 20

    "There Goes"

    From: 'Everything I Love' (1996)

    This lonesome country tune finds the narrator bemoaning a failed romance. It’s the fourth single from Jackson’s 1996 album, Everything I Love, which spawned six radio singles.

  • 19

    "Right on the Money"

    From: 'High Mileage' (1998)

    Penned by Charlie Black and fellow country singer-songwriter Phil Vassar, this 1998 cut was Jackson’s sixteenth No. 1 single.

  • 18

    "Country Boy"

    From: 'Good Time' (2008)

    This loud and proud “I’m a country boy” proclamation was sort of a lite prequel to the infamous bro-country era which, like Jackson’s song, is full of songs inviting girls to clamber on their four-wheel drive.

  • 17

    "I'll Try"

    From: The Greatest Hits Collection (1995)

    The second single from his first greatest hits collection, this stirring ballad finds Jackson promising his partner to stand by his romantic vows no matter what life throws at them.

  • 16

    "I Don't Even Know Your Name"

    From: 'Who I Am' (1994)

    Serving as the fifth single from his 1994 album, this song’s about a head over heels romance all gone wrong in the most unexpected way.

  • 15

    "Little Bitty"

    From: 'Everything I Love' (1996)

    The lead single off Jackson’s Everything I Love record, this fan-favorite celebrates the joy and blessings that come with life’s simplest things.

  • 14

    "Summertime Blues"

    From: 'Who I Am' (1994)

    Originally recorded and written by rock ‘n’ roll artist Eddie Cochran, Jackson rolled out a euphoric cover of this song as the lead single from his 1994 album, Who I Am.

  • 13

    "She's Got the Rhythm (And I Got the Blues)"

    From: 'A Lot About Livin' (And a Little 'bout Love)' (1992)

    This cheeky wink-at-R&B tune was penned by Jackson and fellow country star Randy Travis. While the song is about a breakup, Jackson delivers it with such vigor and wit that having "the blues" is almost amusing.

  • 12

    "It Must Be Love"

    From: 'Under the Influence' (1999)

    This song was originally recorded by Don Williams in 1979, before Jackson reworked it on his 1999 covers album, Under the Influence. In 2000, it was released as the third single from that record and went on to become another chart-topper.

  • 11

    "Where I Come From"

    From: 'When Somebody Loves You' (2000)

    Serving as Jackson’s 18th No. 1 hit, this up-tempo song is centered around a truck driver who constantly faces the need to elucidate the southern way of life that he’s used to.

  • 10

    "Tall, Tall Trees"

    From: The Greatest Hits Collection (1995)

    Another single from Jackson’s The Greatest Hits Collection album, this ecstatic love song was written and originally recorded as album cuts by country legends George Jones and Roger Miller. Here, an infatuated Jackson promises his sweetheart a “great big mansion,” “tall, tall trees, and all the waters and the seas,” and more.

  • 9

    "Remember When"

    From: 'Greatest Hits Volume II' (2003)

    On this tender, nostalgia-driven song, Jackson takes a trip down memory lane as he reflects on the life he’s shared with his wife Denise, and the children they continue to bring up together.

  • 8

    "Gone Country"

    From: 'Who I Am' (1994)

    Written by Bob McDill (Sammy Kershaw, Crystal Gayle, Waylon Jennings), this 1994 cut pokes fun at artist-wannabes who decide to pursue a career in country music because of its popularity and “all the records that everyone’s buying.” It’s just a lighthearted, tongue-in-cheek tune that will make everyone grin.

  • 7

    "Don't Rock the Jukebox"

    From: 'Don't Rock the Jukebox' (1991)

    In this song, an emotionally-shattered man pleads with the people in the bar to not play rock music. He’s distraught after a breakup, and he needs country music to mend that broken heart.

  • 6

    "Small Town Southern Man"

    From: 'Good Time' (2008)

    Jackson and his producer Keith Stegall did an excellent job at making this 2007 track relatable to everyone, regardless of whether they grew up in a big city or small town. Its easy melody instantly transports listeners to the character’s “natural way of life” and has them wishing they were actually a part of it.

  • 5

    "It's Five O'Clock Somewhere" (ft. Jimmy Buffett)

    From: 'Greatest Hits Volume II' (2003)

    This 2003 release held steady at No. 8 on the Billboard Hot Country Songs chart for eight weeks, making history as Jackson’s longest-standing chart-topper. It also doubled as Jackson’s massive crossover pop hit and won a CMA Vocal Event of the Year award in 2003.

  • 4

    "Where Were You (When The World Stopped Turning)"

    From: 'Drive' (2002)

    This song sat at No. 1 for five weeks on the Billboard Hot Country Songs chart. Jackson shared the self-penned tune in the wake of the country’s grieving after the 2001 9/11 attacks. It chronicles the physical, mental, and emotional toll Americans were struck with following the tragedy. Above all, Jackson reminds listeners of a biblical lesson that still holds true today: "faith, hope and love are some good things He gave us, and the greatest is love.”

  • 3

    "Livin' on Love"

    From: 'Who I Am' (1994)

    This catchy and buoyant love song is the perfect summer road-trip sing-along track. Since Jackson released it in 1994, he’s got everyone “livin’ on love” and “buyin’ on time” – which isn’t a shabby way to live life at all.

  • 2

    "Chattahoochee"

    From: 'A Lot About Livin' (And a Little 'bout Love)' (1992)

    Irrefutably the quintessential and most recognizable Alan Jackson tune, this one has truly transcended generations of country fans. It’s always a party whenever the opening lick comes on. This song was released as a single in 1993 and rose to the top of the charts just 20 weeks later. Today, it boasts a whopping 124 million streams on Spotify alone.

  • 1

    "Drive (For Daddy Gene)"

    From: 'Drive' (2002)

    A beautiful tribute to Jackson’s father, this song chronicles the lessons the elder Jackson has imparted to the singer. Things come full circle in the final verse as the country star reflects on his life as a dad with three daughters of his own. At the heart of a good country song is heartfelt storytelling — and this song offers that, and more.

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