80 Songs About Outlaws (Pop, Rap & More)

Foundations of Music

80 Songs About Outlaws (Pop, Rap & More)

I. Pop Songs About Outlaws

1. I Fought the Law by The Clash

Artist: The Clash
Album:
Year: 1977

The song is about a man who breaks the law and is caught by the police. He is put in jail and is unhappy with the way the justice system treats him.

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2. The Wanderer by Dion DiMucci

Artist: Dion DiMucci
Album: Runaround Sue
Year: 1961

The song is about a man who is a wanderer and has no home. He has been everywhere and seen everything. He is tired of moving around and wants to find a place to settle down.

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3. Rebel Yell by Billy Idol

Artist: Billy Idol
Album: Rebel Yell
Year: 1983

The song is about a young rebel who is looking for a place to belong. He is angry and frustrated with the world and is looking for a way to release his anger. He finds release in the form of a rebel yell, which is a cry of defiance and rage. The rebel yell is a way for him to express his dissatisfaction with the world and to release his pent-up anger.

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II. Christian Songs About Outlaws

1. I Can Only Imagine by MercyMe

Artist: MercyMe
Album: The Worship Project
Year: 1999

The song is about a person imagining what it will be like to be in heaven. The person imagines being in a beautiful place with no more pain or suffering. They imagine being reunited with loved ones who have died and being able to worship God freely. The song is a reminder that even though we don’t know what heaven will be like, we can trust that it will be better than anything we can imagine.

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2. I Still Believe by Jeremy Camp

Artist: Jeremy Camp
Album: Stay
Year: 2002

The song is about continuing to believe in God even when life is hard. Camp sings about how God has always been there for him, even when things were tough, and how he knows that God will never leave him. The song is a reminder to keep faith even when things are tough, because God is always with us.

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3. Savior by Rise Against

Artist: Rise Against
Album: Appeal to Reason
Year: 2008

The song is about a person who is struggling and feels lost, but finds hope in the idea of a savior. The lyrics talk about how this savior can help us find our way when we’re lost, and how they can give us strength when we’re weak.

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4. Who Am I by Casting Crowns

Artist: Casting Crowns
Album: Casting Crowns
Year: 2003

The song is about a person questioning their identity and purpose in life. They wonder who they are and why they are here. The song is a reminder that we are all children of God and we each have a unique purpose in His plan.

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5. In Christ Alone by Keith & Kristyn Getty

Artist: Keith & Kristyn Getty
Album: In Christ Alone
Year: 2006

“In Christ Alone” is a song by Keith and Kristyn Getty, written in 2001. The song is based on the apostle Paul’s statement in 1 Corinthians 15:3 that “Christ died for our sins according to the Scriptures.” The song reflects on the sacrifice of Jesus Christ on the cross and the victory he achieved over death.

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6. Amazing Love (You Are My King) by Newsboys

Artist: Newsboys
Album: Adoration: The Worship Album
Year: 2003

The song is a worship song about the amazing love of God. It talks about how God is our King and how His love is unending. It is a song of praise and thanksgiving to God for His love.

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III. Latest Songs About Outlaws

1. I’m The Only Hell My Mama by Johnny Paycheck

Artist: Johnny Paycheck
Album: Country Legend Vol. 26
Year:

The song is about a man who is reflecting on his life and how he has been a disappointment to his mother. He talks about how he has been in and out of jail, and how he has never been able to hold down a job. He talks about how he has always been a troublemaker, and how his mother has always had to bail him out. In the end, he says that he is the only hell his mother ever knew.

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2. Outlaws & Outsiders by Cory Marks, Travis Tritt, Mick Mars, Ivan L. Moody

Artist: Cory Marks, Travis Tritt, Mick Mars, Ivan L. Moody
Album: Who I Am
Year: 2020

Cory Marks, Travis Tritt, Mick Mars, and Ivan L. Moody sing about being outlaws and outsiders. They talk about how they don’t fit in with the rest of the world and how they’re proud to be different.

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3. We Are the Cowboys by Willie Nelson, Billy Joe Shaver, Kris Kristofferson, Waylon Jennings

Artist: Willie Nelson, Billy Joe Shaver, Kris Kristofferson, Waylon Jennings
Album: Honky Tonk Heroes
Year: 1994

The song is about the cowboys and their way of life.

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4. Only Hell My Mama Ever Raised, The by Johnny Paycheck

Artist: Johnny Paycheck
Album: Slide off Your Satin Sheets
Year: 1977

The song is about a man who is down on his luck and has made some bad choices in life. He is reflecting on his childhood and how his mother was the only one who ever raised him right. He is regretful for the choices he has made and how they have led him to this point in his life.

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5. Move It on Over by George Thorogood

Artist: George Thorogood
Album: Move It On Over
Year: 1978

The song is about a man who is down on his luck and is trying to find his way in life. He has been kicked out of his home and is living on the streets. He is trying to find a job, but no one will hire him. He is trying to find a place to sleep, but no one will let him stay. He is trying to find a way to make it in life, but it seems like everything is against him.

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6. Outlaw by Morgan Wallen

Artist: Morgan Wallen
Album: Dangerous: The Double Album
Year: 2021

“Outlaw” is a song by American country music singer Morgan Wallen. It was released on February 1, 2019, as the third single from his debut studio album, If I Know Me (2018). The song was written by Wallen, Michael Hardy, and Ryan Vojtesak.

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7. Family Tradition by Hank Williams Jr.

Artist: Hank Williams Jr.
Album: Hank Williams, Jr.’s Greatest Hits
Year: 1982

The song is about Hank Williams Jr.’s family tradition of country music. He talks about how his father, Hank Williams, was a country music legend and how he wants to continue the tradition. He also talks about how country music is a part of his family’s heritage and how they are all proud of it.

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8. Mammas Don’t Let Your Babies Grow Up to Be Cowboys by Waylon Jennings & Willie Nelson

Artist: Waylon Jennings & Willie Nelson
Album: Willie and Family Live
Year:

The song is a duet between Waylon Jennings and Willie Nelson, and it is a country song about a mother’s warning to her son about the dangers of growing up to be a cowboy.

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9. Sundown (Ballad of Bill Thaxton) by Marty Robbins

Artist: Marty Robbins
Album:
Year:

The song is about a man named Bill Thaxton who is facing execution at sundown. He reflects on his life and how he got to this point. He thinks about his wife and child and how they will never see him again. He also thinks about the woman he loved who is now married to someone else. As the sun sets, he thinks about how his life will soon be over.

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10. Outlawz by Rick Ross

Artist: Rick Ross
Album: Richer Than I Have Ever Been
Year: 2021

The song is about Rick Ross’ life as an outlaw, and how he’s been able to evade the law for so long. He talks about his criminal exploits, and how he’s never been caught. He also talks about how he’s always been one step ahead of the law, and how he’s never been afraid to take risks.

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11. Outlaw by Rick Ross

Artist: Rick Ross
Album: Richer Than I Have Ever Been
Year: 2021

The song is about a man who is an outlaw and lives a life of crime. He is proud of his life and doesn’t care about the consequences. He is unafraid of the police and doesn’t care about the law. He is a danger to society and is proud of it.

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12. Cream Johnny by Night Beats

Artist: Night Beats
Album: Outlaw RnB
Year: 2021

“Cream Johnny by Night Beats” is a song about a young man who is addicted to drugs and alcohol. He is living a life of partying and recklessness, and his addiction is slowly destroying him. The song is a warning to others to be careful of their own addictions, and to not let themselves fall into the same trap as Johnny.

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13. Never Look Back by Night Beats

Artist: Night Beats
Album: Outlaw RnB
Year: 2021

The song is about a relationship that ended and the person regrets not being able to fix it. They think about what could have been and how things could have been different.

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14. Stuck in the Morning by Night Beats

Artist: Night Beats
Album: Outlaw RnB
Year: 2021

The song is about a person who is stuck in a morning routine and can’t seem to break out of it. The person is trying to find a way to escape the monotony and find something new to do.

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IV. Rap Songs About Outlaws

1. Gangsta’s Paradise by Coolio, Kylian Mash

Artist: Coolio, Kylian Mash
Album: Gangsta’s Paradise
Year: 1995

The song is about a gangster’s life and how it is a paradise for them. They live a life of luxury and violence, and they wouldn’t have it any other way.

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2. Dear Mama by Tupac Shakur

Artist: Tupac Shakur
Album:
Year:

The song is a tribute to Tupac’s mother, Afeni Shakur. He talks about how she was a strong black woman who raised him by herself and how she always put her children first. He talks about how she was always there for him, even when he was in trouble. He talks about how she is the reason he is the man he is today and how he will always love her.

3. All Eyez on Me by Tupac Shakur

Artist: Tupac Shakur
Album: Special
Year:

“All Eyez on Me” is a song by American rapper Tupac Shakur. It was released on February 13, 1996, as the lead single from his fourth studio album of the same name. The song features guest vocals from American rapper Big Syke. Production for the song was handled by QDIII and Johnny “J” Jackson.

4. I Get Around by Tupac Shakur

Artist: Tupac Shakur
Album: Strictly 4 My N.I.G.G.A.Z.
Year: 1993

“I Get Around” is a song by American rapper Tupac Shakur. It was released as the second single from his fourth studio album, All Eyez on Me (1996). The song features a guest appearance from fellow rapper Roger Troutman and was produced by Johnny “J” Jackson. The song is a tribute to the West Coast hip hop lifestyle. It peaked at number 11 on the Billboard Hot 100 and was certified platinum by the Recording Industry Association of America (RIAA).

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5. Outlaw by 50 Cent

Artist: 50 Cent
Album: Outlaw
Year: 2011

The song is about how 50 Cent is an outlaw who does whatever he wants. He doesn’t care about the law or anyone else. He is just out for himself.

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6. Outlaws by The Dayton Family

Artist: The Dayton Family
Album: Welcome to the Dopehouse
Year: 2002

The song is about a group of friends who are all outlaws. They are all in love with the same girl, but she is in love with someone else. They all live for the thrill of the outlaw life, and they would do anything for her.

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7. Ambitionz Az a Ridah by Tupac Shakur

Artist: Tupac Shakur
Album: All Eyez on Me
Year: 1996

The song is about Shakur’s ambition to become a successful rapper and to make money. He talks about how he is not afraid to die for his dreams and how he will never give up.

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8. California Love by Snoop Dogg, Tupac Shakur

Artist: Snoop Dogg, Tupac Shakur
Album: My Death Row Bro
Year:

This song is about the rappers’ love for the state of California. They sing about the weather, the women, and the overall lifestyle in the state.

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9. I’m An Outlaw by Hussein Fatal, Kwe, B.East

Artist: Hussein Fatal, Kwe, B.East
Album: Fatal
Year: 2002

The song is about being an outlaw, or someone who is outside of the law. The lyrics talk about how the speaker is not afraid of the police or anyone else, and how they will do whatever they want, regardless of the consequences.

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10. Outlaw by Tupac Shakur

Artist: Tupac Shakur
Album: Me Against the World
Year: 1995

The song is about a young man who is tired of being poor and oppressed. He turns to a life of crime to make money and get out of his situation. He is proud to be an outlaw and does not regret his choices.

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11. Tattoo Tears by Tupac Shakur

Artist: Tupac Shakur
Album: Still I Rise
Year:

The song is about the pain of regretting a tattoo, and how it can feel like your skin is crying.

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12. Backwoods Badass by Outlaw

Artist: Outlaw
Album: Backwoods Badass
Year: 2018

The song is about a country girl who is tough and doesn’t take any crap from anyone. She is a badass who can hold her own in any situation.

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13. Outlawz by Rick Ross

Artist: Rick Ross
Album: Richer Than I Have Ever Been
Year: 2021

The song is about Rick Ross’ life as an outlaw, and how he’s been able to evade the law for so long. He talks about his criminal exploits, and how he’s never been caught. He also talks about how he’s always been one step ahead of the law, and how he’s never been afraid to take risks.

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14. For the Outlawz by Moonshine Bandits

Artist: Moonshine Bandits
Album: Whiskey and Women
Year: 2011

The song is about the Outlawz, a group of criminals who are on the run from the law. They are armed and dangerous, and they are willing to do whatever it takes to stay free. The song is an anthem for the Outlawz, and it is a call to arms for all those who are willing to stand up against the law.

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V. R&B Songs About Outlaws

1. Seven Spanish Angels by Willie Nelson, Ray Charles

Artist: Willie Nelson, Ray Charles
Album: Always On My Mind
Year: 1982

The song is about a man who is on his death bed, looking back on his life. He recalls all of the people who have been there for him, including seven Spanish angels. These angels represent the seven virtues: faith, hope, charity, fortitude, justice, temperance, and prudence. The man reflects on how each of these virtues has helped him throughout his life, and how they have brought him to where he is now. He thanks the angels for their guidance, and asks for their forgiveness.

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2. Outlaws by Alessia Cara

Artist: Alessia Cara
Album: Know-It-All
Year: 2015

“Outlaws” is a song by Alessia Cara about feeling like an outsider. The song is about feeling like you don’t belong and feeling like an outcast.

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3. I’m an Outlaw by Tupac Shakur

Artist: Tupac Shakur
Album: Me Against the World
Year: 1995

The song is about being an outlaw and not following the rules. Tupac talks about how he doesn’t care about what other people think and how he does what he wants. He also talks about how he is not afraid of anyone or anything.

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4. Just Like Jesse James by Cher

Artist: Cher
Album: Heart of Stone
Year: 1989

The song is about a woman who is in love with a man who is a outlaw. She knows that he is not good for her, but she can’t help but love him anyway.

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5. Outlaw by Outlawz

Artist: Outlawz
Album: Classic Collabz, Vol. 2
Year: 2019

The song is about the life of an outlaw and how they live outside the law. They talk about how they are not afraid of the police or anyone else, and how they will do whatever they want.

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6. Outlaw by Struggle Jennings

Artist: Struggle Jennings
Album: I Am Struggle
Year: 2013

The song is about a man who is struggling with his demons and trying to find his way in life. He is an outlaw who has been on the run from the law for years. He is tired of running and wants to find a place to rest. He is looking for a place to call home.

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7. Renegades by X Ambassadors

Artist: X Ambassadors
Album: VHS
Year: 2015

The song is about a group of outcasts and misfits who are fighting for a better life. They are fighting against the odds and are determined to make a change. They are united by their cause and are willing to sacrifice everything for it.

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8. Outlaw by 50 Cent

Artist: 50 Cent
Album: Outlaw
Year: 2011

The song is about how 50 Cent is an outlaw who does whatever he wants. He doesn’t care about the law or anyone else. He is just out for himself.

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9. Outlaw by Rick Ross

Artist: Rick Ross
Album: Richer Than I Have Ever Been
Year: 2021

The song is about a man who is an outlaw and lives a life of crime. He is proud of his life and doesn’t care about the consequences. He is unafraid of the police and doesn’t care about the law. He is a danger to society and is proud of it.

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10. Cream Johnny by Night Beats

Artist: Night Beats
Album: Outlaw RnB
Year: 2021

“Cream Johnny by Night Beats” is a song about a young man who is addicted to drugs and alcohol. He is living a life of partying and recklessness, and his addiction is slowly destroying him. The song is a warning to others to be careful of their own addictions, and to not let themselves fall into the same trap as Johnny.

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11. Knives Of New Orleans by Eric Church

Artist: Eric Church
Album: Mr. Misunderstood
Year: 2015

The song is about a man who is on the run from the law. He is heading to New Orleans to hide out. He is armed with a knife and he is ready to use it if he has to.

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12. Never Look Back by Night Beats

Artist: Night Beats
Album: Outlaw RnB
Year: 2021

The song is about a relationship that ended and the person regrets not being able to fix it. They think about what could have been and how things could have been different.

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13. Stuck in the Morning by Night Beats

Artist: Night Beats
Album: Outlaw RnB
Year: 2021

The song is about a person who is stuck in a morning routine and can’t seem to break out of it. The person is trying to find a way to escape the monotony and find something new to do.

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VI. Rock Songs About Outlaws

1. Bad to the Bone by George Thorogood

Artist: George Thorogood
Album: Bad to the Bone
Year: 1982

The song is about a man who is “bad to the bone.” He is a rebel and a troublemaker, and he doesn’t care what anyone thinks of him. He is proud of his reputation and he is not afraid to show it.

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2. Take This Job and Shove It by Johnny Paycheck

Artist: Johnny Paycheck
Album: Take This Job And Shove It
Year: 1977

The song is about a man who is fed up with his job and tells his boss to take the job and shove it. He is tired of working long hours for little pay and is ready to move on.

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3. I Fought the Law by The Clash

Artist: The Clash
Album:
Year: 1977

The song is about a man who breaks the law and is caught by the police. He is put in jail and is unhappy with the way the justice system treats him.

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4. The Times They Are A-Changin’ by Bob Dylan

Artist: Bob Dylan
Album: The Times They Are a-Changin’
Year: 1964

The song is about how the world is constantly changing and how people need to change with it. Dylan sings about how the old ways of doing things are no longer effective and how people need to adapt to the new ways. He also talks about how the future is always unknown and how people need to be prepared for it.

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5. Runnin’ with the Devil by Van Halen

Artist: Van Halen
Album: Van Halen
Year: 1978

The song is about a person who is living a life of sin and is on the path to destruction. The person is warned about the dangers of running with the devil, but they continue to do so anyway.

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6. The Ballad of Billy the Kid by Billy Joel

Artist: Billy Joel
Album: Live In The Studio – Sigma Studios 1972
Year: 1972

The song is about a young man named Billy who is an outlaw. He is on the run from the law and is being hunted by a posse. He is also being hunted by a woman who is in love with him.

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7. Wanted Dead or Alive by Bon Jovi

Artist: Bon Jovi
Album: Slippery When Wet
Year: 1986

The song is about a cowboy who is on the run and doesn’t want to be caught. He is willing to do whatever it takes to stay free.

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8. Born to Run by Bruce Springsteen

Artist: Bruce Springsteen
Album: Born to Run
Year: 1975

The song is about a young man’s escape from his hometown. He is in love with a girl named Mary and he wants to take her away to a better life. The song is an anthem for anyone who has ever felt trapped by their circumstances and longed for something better.

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9. Green Grass and High Tides by The Outlaws

Artist: The Outlaws
Album: Outlaws
Year: 1975

The song is about a man looking back on his life and all the things he’s done. He’s proud of his accomplishments but also regrets some of the things he’s done. He’s looking forward to the future and hoping for better days.

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10. Outlaw Man by Eagles

Artist: Eagles
Album: Desperado
Year: 1973

The song is about a man who is an outlaw and is on the run from the law. He is in love with a woman who is also an outlaw and is also on the run. They are both living a life of crime and are constantly on the move. They are always looking over their shoulders for the law, but they are also always looking for each other.

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11. Southern Rock Will Never Die by The Outlaws

Artist: The Outlaws
Album: Dixie Highway
Year: 2020

The song is about the southern rock music genre and how it will never die. The lyrics talk about how the genre has been around for decades and how it is still going strong. The song mentions some of the biggest names in southern rock, such as Lynyrd Skynyrd and The Allman Brothers Band.

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12. English Outlaw by The Dogs D’Amour

Artist: The Dogs D’Amour
Album: …More Unchartered Heights of Disgrace
Year: 1993

The song is about an English outlaw who is on the run from the law. He is in love with a woman who is also an outlaw. They are both trying to escape from the authorities and live a life on the run.

13. Outlaw Women by Hank Williams Jr.

Artist: Hank Williams Jr.
Album: Whiskey Bent and Hell Bound
Year: 1979

The song Outlaw Women by Hank Williams Jr. is a song about the women in Williams’ life who have been a little bit out of the ordinary. He talks about the women he has been with who have been wild and free, and how they have made him feel. He also talks about how he is drawn to these women, and how they have made him feel alive.

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14. (Ghost) Riders In the Sky (Digitally Remastered, 1996) by The Outlaws

Artist: The Outlaws
Album: Ghost Riders
Year: 2014

A cowboy tells a tale of the wild west, where a group of cowboys are chased by a group of ghosts. The cowboys are trying to escape the ghosts, but they are slowly being caught.

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15. Outlaw Blues by Pat Benatar

Artist: Pat Benatar
Album: Tropico
Year: 1984

Outlaw Blues is a song about a woman who is in love with a man who is an outlaw. She knows that he is not good for her, but she can’t help but love him anyway. She knows that he is going to end up getting himself killed, but she can’t seem to stop loving him.

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16. There Goes Another Love Song by The Outlaws

Artist: The Outlaws
Album: Outlaws
Year: 1975

The song is about a man who is reflecting on a past relationship. He remembers all the good times they had together, and how he is now living a life without her. He knows that he can’t go back and change what happened, but he still loves her and misses her.

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17. Song For You by The Outlaws

Artist: The Outlaws
Album: Outlaws
Year: 1975

The song is about a man who is singing to his love, telling her that he will always be there for her and that he will always love her.

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VII. Country Songs About Outlaws

1. Bless the Broken Road by Rascal Flatts

Artist: Rascal Flatts
Album:
Year: 2004

The song is about a man looking back on his life and all the mistakes he has made. He is thankful for all the people who have helped him along the way, even though he has not always been the best to them.

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2. The Times They Are A-Changin’ by Bob Dylan

Artist: Bob Dylan
Album: The Times They Are a-Changin’
Year: 1964

The song is about how the world is constantly changing and how people need to change with it. Dylan sings about how the old ways of doing things are no longer effective and how people need to adapt to the new ways. He also talks about how the future is always unknown and how people need to be prepared for it.

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3. Long Haired Country Boy by Charlie Daniels

Artist: Charlie Daniels
Album: Fire on the Mountain
Year: 1974

The song is about a man who is proud to be a long haired country boy. He talks about how he doesn’t care what people think of him and how he is happy just being himself.

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4. Amazing Grace by LeAnn Rimes

Artist: LeAnn Rimes
Album: You Light Up My Life: Inspirational Songs
Year: 1997

The song is a cover of the traditional hymn “Amazing Grace.” Rimes’ version is a slower, more emotive take on the song, with her powerful voice conveying the message of the lyrics. The song speaks to the power of God’s grace in saving us from our sins, and how it is something that we can always rely on.

https://www.youtube.com/watch?v=iT88jBAoVIM

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5. Take This Job and Shove It by Johnny Paycheck

Artist: Johnny Paycheck
Album: Take This Job And Shove It
Year: 1977

The song is about a man who is fed up with his job and tells his boss to take the job and shove it. He is tired of working long hours for little pay and is ready to move on.

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6. The Old Rugged Cross by Alan Jackson

Artist: Alan Jackson
Album: Precious Memories
Year: 2006

The song is about a person’s love for the old rugged cross. The cross is a symbol of hope and love, and the song reflects on how it has helped the singer in their life. The song is a ballad, and is sung in a slow and emotive style.

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7. Free Bird by Lynyrd Skynyrd

Artist: Lynyrd Skynyrd
Album: (Pronounced ‘Lĕh-‘nérd ‘Skin-‘nérd)
Year: 1973

The song is about a bird that is free to fly away and never has to worry about being caged again. The bird is also a symbol of freedom and liberty.

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8. How Great Thou Art by Carrie Underwood

Artist: Carrie Underwood
Album: Greatest Hits: Decade #1
Year: 2014

The song is a hymn about how great God is and how He is worthy of our praise. Carrie Underwood sings about how God created the world and everything in it, and how He is our protector and guide. The song is a reminder of how much we need God in our lives, and how He is always there for us.

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9. The Weight by The Band

Artist: The Band
Album:
Year:

The Weight is a song written by Robbie Robertson and originally performed by The Band in 1968. The song is about a traveler who arrives in a small town and is asked to stay with a family there. The traveler is then asked to do various tasks for the family, including carrying their groceries and picking up their laundry. As the traveler does these things, he thinks about the people he has left behind and the things he has left undone. The song is about the choices we make in life and how they can weigh us down.

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10. The Legend of Wooley Swamp by The Charlie Daniels Band, Charlie Daniels Band

Artist: The Charlie Daniels Band, Charlie Daniels Band
Album: Full Moon
Year: 1980

The song is about a group of men who get lost in the Wooley Swamp and are never seen again.

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11. Texas (When I Die) by Tanya Tucker

Artist: Tanya Tucker
Album:
Year:

The song is about a woman from Texas who is looking forward to dying and going to heaven. She talks about how she wants to be buried in her home state, and how she wants to be remembered.

12. Mammas Don’t Let Your Babies Grow Up to Be Cowboys by Waylon Jennings & Willie Nelson

Artist: Waylon Jennings & Willie Nelson
Album: Willie and Family Live
Year:

The song is a duet between Waylon Jennings and Willie Nelson, and it is a country song about a mother’s warning to her son about the dangers of growing up to be a cowboy.

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13. Don’t You Think This Outlaw Bit’s Done Got out of Hand by Waylon Jennings

Artist: Waylon Jennings
Album: I’ve Always Been Crazy
Year: 1978

The song is about a man who is reflecting on his life of crime and how it has caught up to him. He is now on the run from the law and is looking back on his life with regret.

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14. Are You Sure Hank Did It This Way by The Highwaymen

Artist: The Highwaymen
Album: The Essential Highwaymen
Year: 2010

The song is a story about a man who is questioning whether or not Hank did things the right way. The man is clearly not happy with the way Hank did things and is questioning his choices.

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15. Mama Tried by Merle Haggard, Mac Wiseman

Artist: Merle Haggard, Mac Wiseman
Album:
Year:

The song is about a man who has led a life of crime and is now facing the consequences. He reflects on how his mother tried to steer him down the right path, but he didn’t listen. Now he’s in jail and regrets the choices he made.

16. High Cost of Living by Jamey Johnson

Artist: Jamey Johnson
Album: That Lonesome Song
Year: 2008

The song is about the financial struggles that many Americans face. The high cost of living is a major problem for many people, and the song highlights some of the ways that people are struggling to make ends meet. The song also talks about how people are trying to find ways to save money, but often times it is not enough.

https://www.youtube.com/watch?v=GpEOmZTYA4A

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17. Highwayman by Kris Kristofferson, Waylon Jennings, Johnny Cash, Willie Nelson

Artist: Kris Kristofferson, Waylon Jennings, Johnny Cash, Willie Nelson
Album: The Highwayman Collection
Year: 2000

The song is about a highwayman who robs people who are traveling on the road. He is in love with a woman who is also a highwayman, and they plan to meet up and rob people together. However, the woman is killed by the police before they can meet. The highwayman is left alone and heartbroken.

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18. Cocaine Blues by Johnny Cash

Artist: Johnny Cash
Album: At Folsom Prison
Year: 1968

The song is about a man who is caught with cocaine and is sentenced to death. The man pleads with the judge for leniency, but the judge is not moved. The man is executed and his body is sent to the morgue.

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