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Cole Swindell: His Five Best Number-One Songs

By Nancy Brooks // Country Writer, Beasley Media Group

Cole Swindell has been scoring country music hits since 2013, when he charted his very first number-one song on country radio, “Chillin’ It.” Before that time, he was a Nashville songwriter that moved to town from his native Georgia in 2007 and penned songs like 2013’s “This Is How We Roll” for Florida Georgia Line and 2014’s “Roller Coaster” for Luke Bryan.

Swindell worked for Bryan as a t-shirt-selling guy before he moved to Nashville and began his songwriting journey.

Cole has had a big 2023, as at the ACM Awards in May, he won awards for Song and Single for his collaboration and chart-topper with Jo Dee Messina’s “She Had Me At Heads Carolina.” When he won Song of the Year, he said, “I moved to Nashville, Tennessee because I wanted to be a songwriter, and that’s what this award is. Jo Dee, I wouldn’t have this song without you making the original hit; thank you so much.”

He added, “There’s a kid out there watching this tonight that’s gonna get inspired by a song, and they’re gonna follow it up and chase the dream just like we all did. God bless country music.”

As Swindell celebrates his 40th birthday today (6/30), we ranked five of his number-one songs.

RELATED: Cole Swindell: She Had Me at 'I Do'

  • 5. "Single Saturday Night" - (2020)

    An upbeat, fun tune. Cole said, “The past few months have been hard for everyone, and I wanted to give the fans something fun to kick off summer.” “Single Saturday Night” was what he called a “comfort gift” for fans because his tour was postponed during the COVID-19 pandemic.

  • 4. "Chillin' It" (2013)

    His debut single and his first number-one song. Swindell released the song independently in March 2013 as a digital download. In July 2013, he signed a record deal with Warner Bros. Records Nashville, and they assumed promotion of the single and released it to country radio in August 2013. The song is included on Cole’s self-titled debut album, which was released on February 18, 2014.

  • 3. "Never Say Never" with Lainey Wilson - (2021)

    The first duet from Swindell and Wilson. Cole said when it came out, “I have been a fan of Lainey Wilson’s for a while now, and what she brings to this song is everything it needed.”

  • 2. "You Should Be Here" (2015)

    Swindell and Ashley Gorley wrote this beautiful song as a tribute to Swindell’s father, who died unexpectedly while Cole was out on tour after signing his record deal. The beginning of the music video for this touching song features Swindell sitting in his truck and talking on his cell phone to his dad, telling him he was just signed to Warner Brothers Nashville.

  • 1. "She Had Me at Heads Carolina" - (2022)

    This is a great song and an award winner at May’s (2023) ACM Awards for Single and Song of The Year. The song’s storyline is that the narrator falls in love with a woman who sings “Heads Carolina, Tails California” at a karaoke bar. Jo Dee Messina, who sang the original hit the song is about, makes a cameo in the music video as a bartender. A remix version of the song featuring Messina was released on November 7, 2022.

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