Long before Jelly Roll was a Grammy-nominated country singer, he was an underground rapper with a cult following. He released his first mixtape, The Plain Shmear Tape, in 2003. Since then, he has dropped 21 mixtapes, two EPs, and 18 studio albums including collaborative albums with Struggle Jennings, Haystak, Lil Wyte, and BPZ. However, many of his current fans are only aware of—or interested in—his latest releases, Ballads of the Broken (2021) and Whitsitt Chapel (2023).
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For those who want to get to know a little more about the “Save Me” singer, let’s dive into his deep catalog. Here are three songs that Jelly Roll’s fans were listening to before his country music success seemed like a remote possibility.
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“My Life” from The Hate Goes On (2009)
Jelly Roll released his eighth mixtape, The Hate Goes On in July 2009. By this time, he was already an established member of the Nashville rap scene. Many of the artists he surrounded himself with were fellow gang members and drug dealers. They made Southern-fried “gangsta rap” because they rapped about the lives they lived. As one would expect, themes of violence, drugs, and street life populated the majority of his catalog.
However, Jelly Roll has never been a one-dimensional artist. “My Life” is an early example of his willingness to be vulnerable in his songwriting. He talks about the friends who lost their freedom to selling drugs and his fear of being incarcerated if he gets caught. Then, there are lines like Life is a sacrifice I’m willin’ to lose that / So if you shoot at me I won’t even shoot back that speaks to how fragile his mental health was at the time.
[RELATED: Jelly Roll Would Bring Mixtapes to Drug Deals: “It Was Like My Business Card”]
Most importantly, this song is exactly what the title proclaims—a look into the life of Jelly Roll in the late 2000s.
“Dope Boy Sh-t” from Whiskey, Weed, & Women (2013)
2013 saw Jelly Roll releasing his 20th mixtape, Whiskey, Weed, & Women. The tape’s original title was Whiskey, Weed, & Waffle House. However, the restaurant chain hit him with a cease and desist order. So, he had to change it.
“Dope Boy Sh-t” is another song in which the title lets you know what you’re getting. It’s a song about selling drugs and making music about selling drugs. In the chorus, Jelly Roll says, Everybody love that dope boy sh-t. / Everybody misses that dope boy sh-t. / The radio don’t play that dope boy sh-t.
It’s a little funny to hear this hook today knowing that Jelly Roll stopped releasing “that dope boy sh-t” and now has multiple hit songs.
“Let the Bad Times Roll” from Goodnight Nashville (2018)
Jelly Roll released his 13th studio album Goodnight Nashville in 2018. This was not the first time he played with a blend of rock and hip-hop. However, it’s a great early example of what was to come for the Antioch native. He would go on to release albums like The Whiskey Sessions II in 2019 and Ballads of the Broken in 2021 both further signaled his transition away from being a rapper. He finally completed the transformation in 2023 with Whitsitt Chapel, his debut country album.
[RELATED: Jelly Roll Reveals How Time as Independent Rapper Was Catalyst for Country Music Success]
In “Bad Times Roll”, Jelly Roll raps through the verses. Then, big distorted rock guitars come in for the chorus and he starts singing. The choruses of this song foreshadow his transition away from the genre. It also sees him juggling his past life and focusing on raising his daughter and being a good example for her.
Jelly Roll’s Deep Catalog
The current CMA New Artist of the Year’s catalog contains hundreds of songs that may not seem to fit with the artist—or the man—he is today. However, listening to them with a keen ear will show that he was always on the road to his current life. He’s a successful artist with a happy marriage who is raising his daughter. At the same time, he can unflinchingly share his joy, pain, highs, and lows through his lyrics.
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