33 Best Alan Jackson Songs

Alan Jackson is among the most successful names in country music. Singing on themes of heartbreak, family, and everyday life, his traditional country style resonates with his massive audience. Here are the best Alan Jackson songs ever.

Remember When

Song Year: 2003

This second single from his album Greatest Hits Volume II focuses on his marriage with his wife, Denise. The nostalgic lyrics reminisce about the singer's life, from his childhood memories to his wedding day.

“Remember When” became a huge commercial success, reaching the top of the Billboard Hot Country Songs chart. The song is one of Jackson's most popular tunes. The track received critical praise and received nominations for several awards, including a Grammy Award for Best Country Song.

Livin’ On Love

Song Year: 1994

Released in 1994, this is the second single from his album Who I Am. The song was written by Jackson and his wife, Denise. The song tells the story of a long-married couple who live a simple life, getting by on love and commitment. Despite their modest means, the couple is content with what they have.

The upbeat and catchy melody with a classic country sound features acoustic guitar, steel guitar, and a fiddle. The song reached the top of the Billboard Hot Country Songs chart and became one of Jackson's signature and most popular songs.

Chattahoochee

Song Year: 1993

“Chattahoochee” is the third single from his album A Lot About Livin' (And a Little 'bout Love). Like many Jackson staples, the song is a nostalgic tribute to Jackson's childhood memories. This particular single is about Jackson growing up along the Chattahoochee River. Jackson sings about learning to swim, fishing, and falling in love along the river.

The upbeat tempo, combined with Jackson's distinctive twangy vocals, makes it a favorite among country music fans. The track’s popularity cemented its place as a classic of the country music genre. “Chattahoochee” reached No. 1 on the US Hot Country Songs chart and No. 2 on the Canadian RPM Country Tracks chart.

Country Boy

Song Year: 2008

“Country Boy” is a song about a love for the rural lifestyle and the simple pleasures of the countryside. Jackson sings about hunting, fishing, and spending time with his family and friends.

The song is a catchy ditty with a message of pride in your hometown roots. Fans of the track appreciate that Jackson captures the spirit of the American countryside and the rural way of life. It is recognized as an anthem for country music fans everywhere.

Small Town Southern Man

Song Year: 2008

This song is a tribute to Jackson's upbringing in rural Georgia and his father's influence on his life. The single tells the story of a man who is proud of the values instilled in him by his parents. He works hard, goes to church on Sundays, and treats people with respect. In the song, Jackson takes pride in his hometown, even though it may not be glamorous or well-known.

“Small Town Southern Man” reached the top 10 on the Billboard Hot Country Songs charts due to its message of humility and respect for tradition that resonates with many listeners. The hit remains a beloved song in Jackson's catalog.

It’s Five O’Clock Somewhere

Song Year: 2003

This global classic is a genre-breaking crossover hit thanks to the help of beloved singer Jimmy Buffett. The song written by Jim “Moose” Brown and Don Rollins is the lead single from Jackson's album Greatest Hits Volume II.

The Number One hit on the Billboard Hot Country Singles also reached Number 17 on the Billboard Hot 100 chart. “It's five o'clock somewhere” is a popular saying used to justify drinking at any time of day.

Little Bitty

Song Year: 1996

This lighthearted melody is the lead single from his album Everything I Love. The lyrics describe the joys of life's simple pleasures and encourage listeners to appreciate the small things. The Number One Billboard Hot Country Singles reached crossover success by hitting Number 56 on the Billboard Hot 100 chart.

The popular music video with millions of views on YouTube features Jackson performing on a small stage in a rural setting, with scenes of people enjoying simple pleasures like fishing and picnicking.

Where Were You (When the World Stopped Turning)

Song Year: 2001

Alan Jackson wrote this touching number in response to the 9/11 terrorist attacks in the United States. The song was released as a single from his album Drive. The lyrics reflect on the events of September 11th and the impact they had on the world.

The song broke into the Top 30 on the Billboard Hot 100. It also earned Jackson a Grammy Award for Best Country Song in 2003. And it continues to be a powerful reminder of that unforgettable day for many people.

The Older I Get

Song Year: 2017

From the album Thirty Miles West, this song is a reflection on aging and the wisdom that comes with experience. Jackson acknowledges the challenges of aging, but he also notices the beauty in the memories and relationships that form along the way.

Good Time

Song Year: 2008

“Good Time” is the lead single from his album of the same name. The lyrics describe his desire to enjoy his favorite things, like listening to music, dancing, and spending time with friends. Another crossover success, the Number One country song charted at 39 on the Billboard Hot 100.

Drive (For Daddy Gene)

Song Year: 2002

“Drive (For Daddy Gene)” is the lead single from the album Drive. Written by Jackson, the song is a tribute to his late father Eugene Jackson, who loved driving boats and cars. The song focuses on the memories of a father and son spending time together. Jackson sings about how those experiences influenced his life.

“Drive (For Daddy Gene)” hit Number One on the Billboard Hot Country Singles and Number 28 on the Billboard Hot 100 charts. The sentimental song also won the 2003 Grammy Award for Best Country Song.

Don’t Rock The Jukebox

Song Year: 1991

“Don't Rock the Jukebox” is an early hit and the lead single from his second studio album of the same name. The song was co-penned by Jackson, Keith Stegall, and Roger Murrah. In the song, Jackson vows to leave the jukebox alone and not play sad songs.

The Billboard Hot Country Singles and Tracks Number 1 hit helped establish Jackson as a major country music star. The popular music video features Jackson in a honky-tonk bar. The video popularized the singer’s signature look of a cowboy hat and traditional country outfits.

Gone Country

Song Year: 1994

This third single from the album Who I Am tells the story of aspiring musicians moving to Nashville trying to make it in the country music industry.

The Number One Billboard Hot Country song focuses on artists moving to Nashville in pursuit of fame. The 1995 ACM Award for Single of the Year was also nominated for the 1996 Grammy Award for Best Male Country Vocal Performance.

She’s Got the Rhythm (And I Got the Blues)

Song Year: 1992

This number one hit was co-written by Randy Travis. The song is another successful single from the 1992 album A Lot About Livin' (And a Little 'bout Love). The single tells about a man captivated by a woman's ability to dance and move to the rhythm of the music. Jackson compares this woman to a river and admits he is not the best dancer. He is still drawn to her and can't help but feel the rhythm and blues of the music.

The song's clever lyrics tell the listener that the woman with the rhythm is over her relationship with Jackson. She is expressing her newfound freedom by dancing. Over 30 years later, “She’s Got the Rhythm (And I Got the Blues)” is still one of the legendary singer’s most popular songs.

Summertime Blues

Song Year: 1994

This old school hit is a song originally written and recorded by Eddie Cochran in 1958. but has been covered by numerous artists. Some famous rock bands covering the classic include Rush and The Who. The Alan Jackson version is on his album Who I Am.

The song tells the transcendent tale of a young man unable to enjoy his summer because of being denied access to resources. He complains about his job, lack of money, and the restrictions of his parents and authority figures. Jackson's version remains faithful to the original, with its driving rock and roll beat and catchy guitar riff. His rendition helped introduce a new generation of fans to the classic rock and roll hit.

Pop a Top

Song Year: 1999

This Nat Stuckey penned tune is recorded by Alan Jackson for his album Under the Influence. Jim Ed Brown originally recorded the song in 1967. Artists like Conway Twitty and Heartbeat have covered it over the years. The classic song is about a man feeling blue and needing a drink to lift his spirits.

He pops a top and opens a cold beer to help him forget his problems. As he drinks, he reminisces about lost love and happier times. But he ultimately decides to not let his troubles get the best of him. Jackson's version broke into the Top 5 on the Billboard Hot Country Singles & Tracks chart.

Here in the Real World

Song Year: 1990

“Here in the Real World” is the title track from Alan Jackson's debut studio album. The song tells the story of a young man disillusioned by the fantasy world of movies and television and false promises of fame. Jackson is a man tired of living in a world of make-believe. He soon comes to appreciate the simple joys.

The song is a contrast to the fantasy world of Hollywood. And it focuses on the challenges of real life. Jackson's smooth vocals earned this hit a Top 5 spot on the Billboard Hot Country Singles & Tracks.

The Blues Man

Song Year: 1998

“The Blues Man” is a Hank Williams Jr. hit famously covered by Alan Jackson. The original version was recorded in 1980 by Williams. But Jackson released his cover on his album High Mileage.

Written and performed by country musicians, the song actually describes a blues musician living a hard life of ups and downs. Jackson's version was yet another Top 5 on the Billboard Hot Country Singles & Tracks chart.

Midnight in Montgomery

Song Year: 1992

This fourth single from the album A Lot About Livin' (And a Little 'bout Love) is a tribute to the late country music legend, Hank Williams Sr. Jackson sings about a mystical experience he has while visiting Montgomery, Alabama. He hears Williams' voice and feels his presence while contemplating the legacy of Hank Williams.

For a list of popular songs from the era of Hank Williams, click here.

Sissy’s Song

Song Year: 2009

This heartbreaker is in memory of a close friend's wife who passed away suddenly. The song is a single on the album Good Time. Jackson calls his friend’s wife “Sissy” and sings about his feelings of grief and loss that came with her passing.

The heartfelt, personal song was another of his many hits and again broke the artist into the Top Five of the Billboard Hot Country Songs charts. Its honest message of celebrating the life and memories of loved ones who have passed away resonates with listeners.

I Don’t Even Know Your Name

Song Year: 1995

This hit tells the story of a man who meets a woman at a bar and spends the night with her. Surprisingly, he wakes up the next morning without ever knowing her name. Jackson reflects on the wild, carefree night the strangers shared. But he also acknowledges his emptiness and loneliness after she has gone.

I’ll Try

Song Year: 2002

“I'll Try” is a song of love and loyalty written by Brent Keith and Bill Shore. The track speaks about a man and his promise to be there for his lover through thick and thin. Jackson vows to try his best to make things work.

Jackson's deep vocals and the song's simple arrangement give this hit song a tender, heartfelt quality. “I'll Try” is sometimes played at weddings and other romantic occasions. The song's message of commitment and dedication has made it a popular choice for couples who want to express their love and devotion to one another.

Tall Tall Trees

Song Year: 1995

“Tall Tall Trees” is a single from the Greatest Hits Collection compilation album. The song by George Jones and Roger Miller was recorded by George Jones in 1958. The honky-tonk hit features a fiddle and twangy steel guitar. The song tells the story of a heartbroken man.

The singer feels like a small tree in a forest of tall trees, unable to stand out or capture attention. The Top 10 country hit earned Jackson a nomination for Best Male Country Vocal Performance at the 1997 Grammy Awards.

Who’s Cheatin’ Who

Song Year: 1997

“Who's Cheatin' Who” is another cover song by Alan Jackson. The Number Two country hit is a single from the album Everything I Love. The song is about infidelity. It was written by Jerry Hayes and recorded by popular musician Charly McClain in 1980. Jackson sings about broken trust and wonders which one is cheating on the other. The successful single earned Jackson a Best Male Country Vocal Performance at the 1998 Grammy Awards.

Where I Come From

Song Year: 2000

This traditional country ditty is a single from the Jackson album When Somebody Loves You.

The title explains it all, but the song is about his roots and the small town where he grew up. As he commonly does, Jackson reminisces about the simple life and values he learned growing up.

As is the fashion of traditional country songs, Jackson celebrates the importance of family, hard work, and community. He also pays tribute to the traditions and culture of rural America.

This Number One hit on the Billboard Hot Country Songs became one of his most popular and most recognized songs. The hit song has been covered by other country singers including Lullaby Players.

So You Don’t Have to Love Me Anymore

Song Year: 2012

In this well-loved ballad, Jackson sings about a failed relationship and the pain of a breakup. He sings to his lost love of his understanding that the two could not make it work. His biggest request is that she doesn't stay out of obligation or pity. The popular song gave Jackson another Number Two Billboard hit. Fans of Jackson relate to the universal themes of love and loss.

Wanted

Song Year: 1991

Meet Alan Jackson’s chart-topping hit. “Wanted” is the groundbreaking track released on the album Here in the Real World. The popular single was co-written by Charlie Craig. The track is one of Jackson's biggest hits on the Billboard Hot Country Songs charts. Like so many songs on this list, Jackson sings about his love of a woman. Only in this song, Jackson is hopelessly in love and longing.

Rainy Day in June

Song Year: 1995

“Rainy Day in June” is a single from The Greatest Hits Collection. “Rainy Day in June” represents a relationship that has fallen apart. In the tune, Jackson reflects on the good times and laments the end of the relationship. The popular song captures the bittersweet feelings of loss and nostalgia that come with the end of a romance.

Hard Hat and a Hammer

Song Year: 2010

“Hard Hat and a Hammer” is a ballad for fans of Alan Jackson. The song pays tribute to the working class and the blue-collar jobs that keep America running. Jackson sings about traditional family values and the dignity and pride that comes with hard work. Jackson takes pride in the satisfaction that comes from a job well done.

“Hard Hat and a Hammer” is the perfect showcase of Jackson's ability to capture the spirit of the American working class. The single is an anthem for his blue-collar fans, and it has even been an anthem for some labor unions and organizations.

Chasin’ That Neon Rainbow

Song Year: 1990

This classic country song written by Alan Jackson and Jim McBride is the second single from Jackson's debut album, Here in the Real World. Jackson sings about a young man who dreams of making it big in the music industry. He builds his career by playing in dive bars and honky-tonk joints. Chasing that neon rainbow in the song is a metaphor for the bright lights of fame.

Working long and hard nights, Jackson never loses his love for music and keeps chasing that neon rainbow. The single became a Number Two hit for Jackson on the Billboard Hot Country Singles & Tracks chart.

I’ll Go On Lovin’ You

Song Year: 1998

This popular track is an example of Alan Jackson's brilliant songwriting and ability to capture the beauty of true love. The hit single was released from the album High Mileage. Jackson recorded the song in both English and Portuguese. The dual-language version was recorded alongside Brazilian singer Leandro of the musical duo Leandro e Leandro.

“I’ll Go On Lovin’ You” displays Jackson's signature traditional country sound. The lyrics express a deep and enduring love as Jackson promises to stay committed to his partner through good times and bad. The Number 3 hit on the Billboard Hot Country Singles & Tracks is a popular choice for weddings and romantic occasions.

Designated Drinker

Song Year: 2002

“Designated Drinker” is a collaboration with American country singer George Strait. Both Jackson and Strait sing a duet about the ups and downs of being a “designated drinker”. The singers suggest that it is hard being the designated driver, but it is worth it to enjoy the company of friends without worry.

“Designated Drinker” broke the Top 5 on the Billboard Hot Country Singles & Tracks chart. The massive hit also earned Jackson another Grammy Award nomination in 2003. The song is part of Jackson’s live set as he still tours after over 30 years in the industry. His live schedule is available on his official website.

Murder on Music Row

Song Year: 2000

“Murder on Music Row” is a song written and recorded by Larry Cordle and Larry Shell in 1999. Country superstars Alan Jackson and George Strait covered the track for Jackson's album When Somebody Loves You one year later. The controversial lyrics address the perceived decline of traditional country music and the increasing popularity of more pop-influenced country music on Music Row in Nashville, Tennessee.

Many fans disagree and the song represents past beliefs of more traditional country music. The lyrics suggest that this change is a “murder” of traditional country music. The song barely broke the Top 40 when it reached number 38 on the Billboard Hot Country Singles & Tracks chart. And although it was polarizing, “Murder on Music Row” won the Country Music Association (CMA) Award for Vocal Event of the Year in 2000.

Top Alan Jackson Songs, Final Thoughts

Alan Jackson has dozens of number-one hits on the Billboard Hot Country Songs charts and is one of the most successful runs of any country music artist. The legendary country singer has sold over 75 million records worldwide and is one of the best-selling music artists of all time.

Alan Jackson won a Grammy Award in 2003 for “Where Were You (When the World Stopped Turning).” He also won in 2009 for Best Country Collaboration with Vocals for “Country Boy” with George Strait and Jimmy Buffett. Fans of Jackson and country music can enjoy his music for generations.