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The Most Heartbreaking Chris Young Songs That Will Make You Cry

If country music had a heartbreak hotline, you can bet Chris Young would be the voice on the other end. Known for his rich baritone and lyrics that shoot through…

Chris Young performs at the 2024 Let Freedom Sing! Music City July 4th concert on July 04, 2024 in Nashville, Tennessee.
Tibrina Hobson / Stringer via Getty Images

If country music had a heartbreak hotline, you can bet Chris Young would be the voice on the other end. Known for his rich baritone and lyrics that shoot through the heart, Young has a way of turning every heartache into a beautiful song you can’t help but listen to on repeat, even if it breaks your heart into a million pieces every time.  

In this countdown, we’re ranking his most emotional ballads for when you need a good cry in the shower, or a list of songs you can sing during karaoke to bum out your friends (especially the one who always seems to be going through a breakup).  

Why Chris Young’s Ballads are Particularly Effective in Making Someone Cry  

It might be his deep voice or how he’s able to add gravitas to emotional songs, but Young’s ballads have the ability to make listeners feel what he’s singing about. His musical influences, which include his “Mount Rushmore” of country music, Garth Brooks, George Strait, Reba McEntire, and Keith Whitley, also shaped his approach to singing ballads.   

Young is also not one to back down from a challenge, no matter how difficult a vocal performance might be. He’s willing to work with other strong vocalists, plus he has a jazz background and received a scholarship to Berklee College of Music for jazz studies, as well as participated in the Grammy Jazz Choir, which only contributed to his vocal prowess.  

The Top 4 Most Emotional Chris Young Ballads  

Here is our ranking of Young’s most heartbreaking ballads.  

4. “Drowning”  

Chris Young – Drowning (Official Video)   

A heartbreaking track about losing a loved one, the song was inspired by a friend Young lost in a car accident: “I know you're in a better place / One day I'll see you again / But it's killing me we can't be face to face / I miss my best friend.”

3. “The Man I Want to Be”  

Chris Young – The Man I Want to Be (Official Video)  

A tender ballad about wanting to be a better person for the one you love, this one follows a man who is asking for forgiveness and another chance after past mistakes: “Beggin' for another chance / If there's any chance at all / That You might still be listenin' / Lovin' and forgivin' guys like me.”  

2. “Sober Saturday Night”  

Chris Young - Sober Saturday Night (feat. Vince Gill)  

Featuring Vince Gill, this track talks about not using alcohol to nurse heartbreak on a Saturday night and face the Sunday feeling: “All messed up, all strung out, I was sitting at home breaking down / I'm not out there getting high underneath some neon lights / Ain't no whiskey strong enough to make things right / I'm just getting over another sober Saturday night.”

1. “Flowers”  

Chris Young - Flowers   

One of the most heartbreaking songs in his catalog, “Flowers” describes the story of drunk driving, regret, and heartbreak: “I still see you on your knees / Begging me not to drive / But I took away the keys / And made you climb inside / And I'd take your place in this field of stone / If I only had to power / Look what it took / For me to finally bring you flowers.”  

Originally covered by Billy Yates in 1997, Young made the song his, with his signature baritone voice.