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Our 10 Best Chris Stapleton Songs list will look at songs from a talented singer, songwriter, musician, and producer. He has written or co-written over 170 songs to date. He has co-written at least six number one country songs. He was the lead singer in two bands before becoming a solo artist. Some of his hit songs include “Tennessee Whiskey,” “Broken Halos,” “You Should Probably Leave,” “Starting Over,” Parachute,” and “Nobody to Blame,” as well as other hit songs. His albums have gone gold or platinum. His albums topped the country charts and peaked in the top five on Billboard 200. This is an amazing feat. Fans really enjoy his music. He has been nominated for 138 awards and won 64 to date.
Chris Stapleton has written songs for other artists, but he has written amazing songs for himself. He sings about a variety of things. He talks about being in love, and appreciating what you have in life, and death as well as other subjects. His soulful and tenor vocals will sound amazing no matter what he is singing. He has brought a positive vibe back to country music. His songs are what country music needs. He has brought new life to the genre. His songs will make you fall in love with country music.
Longtime fans of Chris Stapleton know his music and appreciate his talent for writing and singing. Our 10 Best Chris Stapleton Songs list will give casual fans a chance to get to know his music and give avid fans a chance to go down memory lane. These songs should be on your playlist. Chris Stapleton’s songs are essential because he is a brilliant storyteller who knows how to make a story come to life. You don’t have to be a fan of country music to be a fan of his. He will reel you in with the stories he tells in every song.
# 10 – Blow – Ed Sheeran ft. Chris Stapleton and Bruno Mars
The 10th song on our 10 Best Chris Stapleton Songs list is “Blow.” “Blow” is on Ed Sheeran’s No. 6 Collaborations Project. “Blow” was released in July 2019. The guys talk about how much the women in their lives drive them crazy in a good way. They express how they feel about the women in their lives. They want to show the women a good time intimately. It’s not just about physical attraction.
They want more than that with women. All the guys talk about how they feel about the women. Ed Sheeran feels like a winner because of her. He loves her so much that he wants a family with her. Chris Stapleton talks about her making him feel weak in the knees. She sets his heart on fire. She has him begging for more. Bruno Mars thinks the woman in his life is sexy. He wants to fulfill her fantasies. He wants to spoil her with the money he has.
This song will please ladies who want a man like any of them. Every woman wants to feel like a queen when it concerns a relationship. Ed Sheeran, Chris Stapleton, and Bruno Mars want more than a physical relationship with women. They talk about intimacy but they keep it classy. This track will be essential to anyone’s playlist because it features three men from different genres of music. Fans get a chance to hear them on one track together. The music has an amazing country and rock beat.
The guitar and drums drive the music. Ed Sheeran, Chris Stapleton and Bruno Mars sound incredible together. They have strong voices that can be heard over the guitar riffs. They do a great job with their vocals. It is great to hear a pop singer, country singer, and r&b singer on the same track. It was a surprise that they all did something different. This song is proof that surprises are a good thing. They need to record more music together. This song deserves more attention than it received.
# 9 – Nobody to Blame
The ninth song on our 10 Best Chris Stapleton Songs list is “Nobody to Blame” from the Traveller album. “Nobody to Blame” was released in November 2015. This song is about a man who is filled with regret. He looks back on what happened in his relationship. His ex made him move out and she destroyed all his things. She changed the locks on him. He goes into detail about the things she destroyed. He wants to take responsibility for their breakup. He has nobody to blame but himself. He knew what he did wrong. He doesn’t elaborate on what he did wrong, but he does accept the blame for the relationship being over.
Chris Stapleton wrote a song about a man who didn’t do what he was supposed to do to keep the relationship alive. He was focusing on the wrong things instead of doing what he was supposed to do. This is a track that everyone can relate to at some point. Chris Stapleton is happily married but he was able to put his mind in a place of heartache.
This track should be added to your Chris Stapleton playlist because he is talking about a relevant situation that people can understand. He talks about a subject that will never get old. He shows that he is a man because he is taking responsibility for his wrongdoing. The music has a traditional country and rock sound. Chris Stapleton combines country and rock music with blues lyrics. You don’t have to be a country music fan to enjoy this song.
# 8 – Millionaire
The eighth song on our 10 Best Chris Stapleton Songs list is “Millionaire” from the From the Room: Volume 1. “Millionaire” was released in April 2018. This humble song is about choosing important things over money. The lyrics talk about being a millionaire if you have love in your heart and someone to love you. He talks about the love of family and friends being worth more than money and fame. He talks about love being worth more than gold. Love can’t be bought. He talks about being in love. The love she has for him makes him feel like a millionaire. They ride around in his beat-up car and people watch them together. They think he is living a life of luxury. Anytime she kisses him, he feels like a millionaire. He may not have money or food, but he feels like a millionaire because he has her.
Chris Stapleton wrote a touching song about love over finances. The protagonist in this song doesn’t have money but feels rich because of the love he has in his life. This song should be added to your Chris Stapleton playlist because of the good message about love being more important than money. It doesn’t matter if you have money and fame if you don’t have anyone to share it with you. Since Chris Stapleton is in the public eye it means even more that he feels rich because he has love in his life. He is someone who can probably buy anything he wants but he prefers the love of the woman in his life. Chris Stapleton sings the song with passion and soul. His wife Morgane Stapleton is singing in the background. Their voices sound magical together. It was a great touch to have her sing in the song. This song is perfect for a wedding song.
# 7 – Either Way
The seventh song on our list is “Either Way” from the From a Room: Volume 1 album. “Either Way” was released in May 2017. This song is about the end of a relationship. He talks about how they don’t love each other anymore. They only talk when they have to. They will pass by each other and not say a word to each other. They sleep in separate rooms. They pretend to have the perfect life in front of people. He doesn’t care anymore about the relationship. He has cried enough over their relationship.
He is ready for her to tell him that it is over. She could stay or go if she wants. He is not going to love her “either way.” The narrator talks about not loving her for a long time. He doesn’t feel anything anymore so she can’t hurt him. He used to spend his nights crying wondering what happened to their relationship. He can only cry about it for so long.
This is a sad song, but it has truth and honesty. He talks about a real relationship that has hit a crossroads. This song is essential to your playlist because people go through a tough time during the end of a relationship. You don’t know if you should stay or go. You are at a point where you don’t care either way if the person stays or goes. Chris Stapleton wrote a song that didn’t have a happy ending.
He chose to write a painful tale about a couple coming to the end of their relationship. Chris Stapleton wrote this song in 2008 for Lee Ann Womack for her album. He remade the song because his wife loved it. He was going to make it believable because his wife has always loved the song. He did the song justice because he sings this song effortlessly. He has a lot of power in his vocals which shows throughout the soft music.
# 6 – Parachute
“Parachute” is from the Traveller album. “Parachute” was released in May 2016. This is a song about a man who has broken up with the woman he loves. He talks about the things he didn’t do for her. He misses her and wants to be there for her the way he wasn’t in the past. If she needs him, he will be there for her like a “parachute.” He talks about how she needed him, but he was never there. He realizes that she didn’t ask for much while they were together. He made the mistake of not providing what she needed.
He never said the things his wife wanted to hear. He also never listened to her when she talked to him. His lack of communication is what helped end the relationship. He wants her to know he wants to be her “parachute.” If she thinks she is going down in life, he wants to be the one who helps her.
This is a song about neglect. He wasn’t there the way he should have been and he wants to make amends for it. He wants to be the emotional support she needs even though they are no longer together. This song is essential to your playlist if you are in a situation where you regret not being there for the person you love. It will teach you to be there when the one you love needs you or else you may end up regretting it.
This song has elements of country music, but it sounds more like a rock song. Chris Stapleton’s voice sounds incredible. You can feel the pain he is feeling over losing the woman he loves. He doesn’t sound desperate when he tries to be there for her even if she doesn’t want anything to do with him. He sounds like he is making amends with her. The music will speak to you even if you aren’t a fan of country music.
# 5 – You Should Probably Leave
The next song on our 10 Essential Chris Stapleton Songs list is “You Should Probably Leave” from the Starting Over album. “You Should Probably Leave” was released in May 2021. This song is about a couple who can’t stay away from each other. They know they are not right for each other, but they can’t seem to stay away from each other. He tells her she should leave before they give into their feelings for each other.
He doesn’t want them to do something they will regret. He doesn’t want them to break up again, so he wants her to go. They agreed to kiss one last time. He is trying to do the right thing, but the devil on his shoulder is advising him not to do it. As the song progresses, we find out that the couple did spend the night together. When they wake up, he hopes she doesn’t tell him he should leave. He hopes she doesn’t regret being with him.
This is a song about temptation and what you may end up doing when you are tempted. This song plays out like a soap opera since the couple broke up and can’t stay away from each other. They couldn’t make their relationship work but there is still an attraction between them. This song is essential to your playlist if you find yourself attracted to someone you broke up with. Chris Stapleton has a brilliant way of building up a story that will keep you hooked until the end.
This song might bring back memories for you if you have been in this situation. What we love about Chris Stapleton is he writes what he feels. He writes about his truth. He doesn’t always paint himself up as the victim. He takes responsibility for his actions. This song had a twist. He didn’t want to make the mistake of being with her again, but he couldn’t resist. The music has a fantastic blues beat that you can feel in your soul. The guitar riffs are fire. Chirs Stapleton’s voice will make you a fan of his music.
# 4 – Say Something – Justin Timberlake ft. Chris Stapleton
“Say Something” is from Justin Timberlake’s Say Something album. This is a thought provoking song about wanting to speak but not having anything to say. Justin Timberlake and Chris Stapleton talk about the pressure from society to say something meaningful. They feel like it is better not to say anything at all. They feel they can say more by keeping silent. People have thought this song was about Justin Timberlake’s comments on social media. People feel like celebrities shouldn’t comment on certain things because they don’t focus on what is important. They believe celebrities do things for themselves instead of the issue at hand.
This song gives Chris Stapleton a chance to write outside of his comfort zone. It is different from the other songs on our list because he is talking about things from a celebrity’s point of view instead of a relationship. He believes in telling honest stories and this one falls in line with that. This song is geared towards Justin Timberlake’s life than his, but he was able to empathize with the situation. Chris Stapleton keeps things honest by talking about someone who is afraid to speak up about something in fear of saying the wrong thing.
This song gives Chris Stapleton a chance to step out of his comfort zone. Chris Stapleton and Justin Timberlake wrote a song about celebrities that won’t have you rolling your eyes. The music has a pop beat with country elements. The country element comes alive once Chris Stapleton sings his verse. His vocals are smoky and soulful in this song. Justin Timberlake and Chris Stapleton have vocal chemistry with each other. The hook is easy to remember and will stay in your head.
# 3 – Broken Halos
Coming in at number three on our list is “Broken Halos” from the From a Room: Volume 1 album. “Broken Halos” was released in April 2017. The touching song is about honoring people who are no longer with us. He talks about how it feels when you lose someone you love before they were supposed to go. He talks about the pain you feel when you lose the person and the road you have to travel to start healing.
He has been dealing with his fair share of loss. He has lost people before their time. The narrator sings about the angels trying to help us get over the pain of losing the person we love. The angels help us and leave to help someone else in pain. He advises people not to ask questions about death because we are not supposed to know about the mystery of death. We know that they belong to God.
This song is a reminder to keep your faith even through tragedy. You are heartbroken over your loss but your faith will get you through it. Chris Stapleton wrote this song in honor of someone he lost. He wrote this about musicians or anyone you love. Everyone has someone in their lives that has gone too soon. This song is special because Chris Stapleton wrote about how it feels to lose someone you love when they have gone too soon.
He talks about the emptiness you feel inside and what you should do to start healing. This is a song that you will release too if you have gone through the pain of losing someone you love. This song is written in a way that isn’t depressing. The music keeps the song from being melancholy. It is like getting advice from a friend. Chris Stapleton sings this song with emotion. You can tell this song means something to him.
# 2 – Starting Over
“Starting Over” is from the album of the same name. This song tells the story of a man who starting a new life. He is leaving his old life behind and starting a new one with the woman he loves. He is ready for a new life, but he knows it won’t be easy to start a new one. The man wants to live a better life. He knows they are going to have problems. There are going to be times when they are angry with each other, but they will make it. He wants them to take a chance on life. They are going to be each other’s good luck charms. You will never win if you are afraid to lose.
The lyrics of the song are deep. Chris Stapleton combined taking a chance in life with being in love. He wants to travel with the person he loves, but he is realistic about it. The singer knows how to paint a realistic picture about things. He doesn’t view the world with rose colored glasses on. He wants to travel with the woman he loves, but he knows it won’t be easy.
He could have told this story without telling the realistic side, but he told an honest story. This song will open your eyes about taking chances and moving forward with your life. Chris Stapleton doesn’t sugarcoat it because he lets you know what could happen when you take a risk. The music has a traditional country sound that will motivate you to start a new life. Chris Stapleton sounds right at home with this song. Chris and Morgane Stapleton’s vocals are smoking hot in this song.
# 1 – Tennessee Whiskey
The number one song on our 10 Best Chris Stapleton Songs list is “Tennessee Whiskey” from the Traveller album. “Tennessee Whiskey” was released in 2015. This song is about a man who compares his lover to his favorite drink. He expresses his gratitude to the woman he loves because she saved him. He used to drink a lot to cope with life. She helped him stop drinking because her love for him gave him everything he needed. Alcohol never gave him what she could give him. He compliments her by comparing her to alcohol. She is what he needed and now he is high on her love instead of alcohol. He looked for love in the bottom of a bottle. He doesn’t have to do that anymore because of her love for him.
This is a warm song about love saving you from addiction. This is more than just a typical love song. It is about salvation. Her love saved him from a potentially deadly addiction. He would rather be hooked on her than on alcohol. People often associate country songs with happy feelings without any depth. This song proves that isn’t the case.
This song is so meaningful and tells an interesting story about love saving your life. The message could be why this is one of Chris Stapleton’s biggest hits. Music lovers can understand these lyrics and feel them in their hearts whether they can relate to them or not. The soulful and bluesy music will restore your faith in music. The music has everything going for it. Chris Stapleton sings this song as if he wrote it. He is singing this song from the heart.
10 Best Chris Stapleton Songs article published on Classic RockHistory.com© 2023
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