Before breaking out as a singer in his own right, Swindell wrote Craig Campbell's "Outta My Head", Thomas Rhett's "Get Me Some of That", and several songs for Luke Bryan, including "Roller Coaster". He also worked as a merchandise vendor for Bryan.
Swindell's debut single "Chillin' It" was issued independently before being picked up by Warner (Bros.) Records Nashville 2013, with his Self-Titled Album following in 2014. A second disc, You Should Be Here, came out in 2016. Alongside these, he has issued four Down Home Sessions extended plays. Except for "Chillin' It", he is under the production of Bryan's guitarist and bandleader Michael Carter.
While sometimes derided as a frontrunner of the contemporary "bro-country" trend, Swindell has put out passionate ballads such as "You Should Be Here" that show a softer side.
- Cole Swindell (2014)
- You Should Be Here (2016)
- All of It (2018)
- Down Home Sessions (2014)
- Down Home Sessions II (2015)
- Down Home Sessions III (2016)
- Down Home Sessions IV (2017)
Tropes present in his work:
- Break-Up Song: Played with on "Break Up in the End", where the narrator acknowledges an on-again, off-again relationship fully aware that the "off-again" part is impending.
- Broken Win/Loss Streak: After his first seven singles all hit either #1 or #2 on the country charts, "Stay Downtown" snapped the streak when it stopped at #28.
- Drowning My Sorrows: "Ain't Worth the Whiskey" plays with this, as the narrator states that he is looking for any excuse to drink that isn't his girl, because she "ain't worth the whiskey".
- Grief Song: "You Should Be Here" has him mourning the loss of a friend.
- Loudness War: Many of the tracks on his first album, most notoriously the jackhammer-sounding drum machine and screeching guitars on "Hope You Get Lonely Tonight". The next two albums aren't quite as bad.
- Rewind Gag: The video for "Break Up in the End" portrays a relationship that is filmed in reverse.
- Spoken Word in Music: Cole says "Tell 'em 'bout it, Dierks" before Dierks Bentley's verses on "Flatliner", and the two have a conversation before the last chorus.