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Wallen compares romances that ultimately come up short with the devastating disappointment of watching a beloved sports team’s winning season falter in the end. This track offers up a slice of nostalgia and heartbreak, as it nods to the Atlanta Braves’ 1998 season, in which a 106-win team ultimately fell short, defeated by the San Diego Padres during six games in the National League Championship Series. “Had a good run, to end up with nothin,’” Wallen sings. Sports and country music have long had close ties, and this track has proven a favorite among both lovers of both.

A collaboration with fellow country artist Eric Church, they sing about divine creation, which in turn leads to manmade locales of solace. “God made a girl, his best work of art/ Oh, but he didn’t make no place to go when she breaks your heart.” Church offers up harmonies and joins on the second verse, as they blend vocals over a mix of guitars, bass, percussion and flashes of mandolin.

He’s living a life many dream of living, but also one that comes with its share of temptations and plenty of time spent away from family. Here, he sings about calling his mom and reassuring her that “I’m still proud of where I came from,” and that her unending prayers for her son are making an impact. Wallen wrote this song with Nicolle Galyon and Miranda Lambert.

The title track from the upcoming I’m The Problem features ripples of guitars and moody percussion, as Wallen levels a defiant clapback to a trash-talking ex-lover. “If I’m so awful, then why’d you stick around this long… you hate that when you look at me, you halfway see yourself,” he sings with a caustic drawl, daring an ex to take partial responsibility for a relationship that didn’t work out. Wallen has made heartbreak anthems a regular part of his musical repertoire, but rarely ones as direct and acerbic as this.

One of a few outside cuts on this list, “Don’t Think Jesus” was written by Jessi Alexander, Chase McGill and Mark Holman. Released in April 2022, “Jesus” reached No. 1 on the Hot Country Songs chart and No. 7 on the Hot 100. The song’s pared-back acoustics venture slightly into more rootsy terrain for Wallen, but it allowed him to offer up one of his most introspective songs, one that squarely looks at acceptance and forgiveness as he sings about a rising artist who “starts writing songs about whiskey and women,” and follows those impulses through a trail of messy mishaps before finding redemption. “I’d shame me, I’d blame me, I’d make me pay for my mistakes/ But I don’t think Jesus does it that way,” he sings.

A deep cut on Wallen’s Dangerous: The Double Album, he ponders why his lover seems to sail away as quickly as a breeze rolls through, only to return occasionally. “She sits there like a feather just waitin’ on a gale,” he muses. Wallen penned this song with fellow artist-writer ERNEST.

This grooving anthem melds country and pop, setting its place as a precursor of sorts to Wallen’s more recent hits. The title track to Wallen’s third studio album, this song finds Wallen singing of setting some post-breakup boundaries. “I ain’t no Superman, I’m just the way I am/ If I’m gonna move on, then I need me something in my hand,” he sings, making it clear that he has his limits and can only focus on breaking ties with one habit in succession.

From his Dangerous: The Double Album, this song earned Wallen a top 10 hit on the Hot 100 in 2020. Waves of guitars, drums and keys put forth this wistful track about longing for an old flame that still burns bright in one’s memory seven years later. Like the enduring recollections in the song, this track still sounds fresh nearly five years later.

A collaboration with genre-fluid artist Post Malone on his 2024 F-1 Trillion album, this radio earworm revels in sarcastic acknowledgement that the faults that led to a couple’s breakup don’t rest solely upon one party. Wallen and Posty match each other’s energy note-for-note, and together, throw a party-ready balm over heartbreak-fueled anger.

“More Than My Hometown” became a top 15 Billboard Hot 100 hit for Wallen in 2020. On this song, he maintains that while a girl might catch his eye and his affections, his hometown has his devotion. Though he and his lover both have small-town roots, she has plans to escape to chase adventures in a big, energetic city, while his ambitions center around a more relaxed life in his hometown. “You got a wild in your eyes that I just wasn’t born with,” he sings, wrapping the lyrics in warmth and believability.

He’s ready to propose to the girl he spent so many nights with in his old Silverado, so he’s ready to pass his beloved truck on to the next love-struck young lad who needs the right pickup truck to “get the prettiest girl in town.” Marv Green, Ben Hayslip and Dallas Davidson wrote this sweetly nostalgic track, included on Wallen’s Dangerous: The Double Album.

All of his favorite hometown spots are marred by the memory of an ex-lover, as he expresses regret over ever having shown his ex any of the places he goes to for fun, solace and respite. An interpolation of The Allman Brothers Band’s “Midnight Rider” puts this twangy heartbreak song in the winner’s circle.

Released prior to Wallen’s upcoming album I’m The Problem, “Superman” is one of his most intimate, vulnerable songs to date, dedicated to his son Indigo Wilder. “I don’t always know my wrong from right/ Sometimes I’m my own worst enemy,” he sings, acknowledging his own foibles and knowing that one day his son will recognize some of his father’s missteps, but also advising his son to face hard times head on and to stand up for himself.

Wallen delves into starkly vulnerable self-examination on this acoustic-driven, redemptive romantic track, a cover of one of Jason Isbell’s most iconic songs (which Isbell previously recorded on his 2013 Southeastern album). Wallen included a version on his 2021 project Dangerous: The Double Album. Written solely by Isbell, Wallen’s version stands tall as one of the strongest recordings in his catalog.

From Wallen’s Dangerous: The Double Album, “Sand in My Boots” is one of Wallen’s most enduring, well-crafted songs. Written by Ashley Gorley, HARDY and Josh Osborne, the song is embedded with a country sensibility and vivid storyline that have worn well since it was released nearly four years ago. The piano-driven ballad centers on a relationship that wasn’t meant to be, as a short-lived romance on the beach ends with the song’s protagonist heading back to east Tennessee, with nothing but sand in his boots as a reminder.