Some fans and enquiring onlookers have connected the names Jelly Roll with Waylon Jennings. Jelly Roll is a multi-genre singer and composer that has been generating waves in the music business since the start of the 2010s. The outlaw fashion in country music started in the 1970s, thanks in significant part to the legendary singer and composer Waylon Jennings.  But are they linked by marriage or by blood? The answer is no, but they do have a unique relationship that involves a different musician.

Jelly Roll: Who Is He?

Jelly Roll’s hometown is Nashville, Tennessee, where Jason DeFord was born in 1986. Due to the difficult circumstances in which he was fostered he was confronted with drugs, violence, and criminality at young ages. He began rapping when he was 15 years old, and his first album was released in 2003. He become prominent in the underground hip-hop scene by cooperating with artists like Tech N9ne, Lil Wyte, and Haystak.  In addition, he experienced legal issues and served some time in jail due to drug-related accusations.

The music of country, rock, and soul were all included into Jelly Roll’s sound as it developed through time. The Big Sal Story, Sobriety Sucks, Addiction Kills, A Beautiful Disaster, and Self Medicated are just a few of the albums and mixtapes he has put out. On several projects, he collaborated with longtime friends and musicians Yelawolf and Struggle Jennings. “Save Me,” “Creature,” “I Need You,” “Love the Heartless,” and “Black Roses” are some of his best-known tracks.

Waylon Jennings: Who Was He?

1937 saw the birth of Waylon Jennings in Littlefield, Texas. He began playing the guitar when he was eight years old, and at the age of fourteen, he gave live radio performances. He dropped out of high school at 16 to focus on his musical career. In clubs and radio stations all around Texas and Arizona, he performed and held a DJ position. He met Buddy Holly in 1958, and they became friends and mentors. Holly hired Jennings to play bass on his tour and set up his first recording session. On the plane that crashed in 1959 and killed Holly, Ritchie Valens, and The Big Bopper, Jennings gave up his seat.

In 1965, Jennings established his own group, The Waylors, and relocated to Nashville. After joining RCA Records, he quickly grew dissatisfied with the label’s creative control over his work. He struggled for the right to express himself freely and created a distinctive style that incorporated elements of country, rock, blues, and folk. Additionally, he revolted against Nashville’s elite and the polished image of mainstream country music. He sung on subjects including drugs, sex, violence, and societal issues while sporting long hair, wearing leather jackets, and wearing denim.

Lonesome, On’ry and Mean, Honky Tonk Heroes, Dreaming My Dreams, Are You Ready for the Country, Ol’ Waylon, I’ve Always Been Crazy, and What Goes Around Comes Around are just a few of the critically praised and financially successful albums that Jennings has made. Along with these musicians, he also worked with Tompall Glaser, Johnny Cash, Kris Kristofferson, David Allan Coe, Hank Williams Jr., Merle Haggard, George Jones, and Jessi Colter (his fourth wife). He was a member of The Highwaymen, a country supergroup that also included Nelson, Cash, and Kristofferson. Are You Sure Hank Done It This Way and Luckenbach, Texas (Back to the Basics of Love) are two of his most well-known songs. I Ain’t Living Long Like This, Mamas Don’t Let Your Kids Grow Up to Be Cowboys, Good Hearted Woman, Amanda, and The Dukes of Hazzard (Good Ol’ Boys) Theme.

Jennings battled heroin addiction for a long time before finally succeeding in the mid-1980s. Up until his health started to deteriorate owing to consequences from diabetes, he kept recording and performing. At the age of 64, he passed away in 2002.

What’s The Relationship Between Waylon Jennings And Jelly Roll?

Waylon Jennings and Jelly Roll are not related by blood or marriage, but there is an intriguing connection between them: Struggle Jennings.

Rapper and musician Struggle Jennings is Waylon Jennings’ step-grandson and the grandson of Jessi Colter. His real name is William Harness Jr., and he is the child of Will Harness Sr., who passed away when Struggle was 10 years old, and Jennifer Eddy (Colter’s Duane Eddy’s daughter from her first marriage.

Struggle was influenced by his grandfather’s legacy and his songs while growing up. He experienced the same difficulties as Jelly Roll since he was involved in crime, drugs, and incarceration. He began performing raps in 2006, and I Am Challenge, his first record, came out in 2013. After being arrested that same year on accusations of trying to distribute cocaine, he was incarcerated to five years in jail.

With the assistance of his producer and pal Scatterbrain, he wrote songs while incarcerated and recorded them over the phone. One of his closest friends and supporters, Jelly Roll, joined him in his creative endeavours. They published Waylon & Willie, their first collaboration album, in 2016 as a tribute to their musical idols and influences. Waylon & Willie II, Waylon & Willie III, and Waylon & Willie IV were all released in 2017, 2018, and 2020, respectfully.

Along with group albums, Struggle also made solo records such Angels & Outlaws, Troubadour of Troubled Souls, The Widow’s Son, The Widow’s Son: Chapter II, and Return of the Outlaw. He collaborated with a variety of musicians, including Yelawolf, his daughter Brianna Harness, Adam Calhoun, Tommy Vext, Caitlynne Curtis, and Shooter Jennings (Waylon’s son).

Struggle claims that Jelly Roll is his brother and that they share a particular bond that extends beyond music. He has also emphasised how proud he is of his grandfather’s past and how he wants to honour it in his own music.


Waylon Jennings and Jelly Roll are not connected by blood or through marriage, but they do have a buddy and collaborator in Struggle Jennings, who is Waylon’s step-grandson. They all belong to a musical family that crosses decades and genres. They have also overcame difficulties and hardships to produce music that connects with many listeners. They serve as illustrations of the power of music to heal, uplift, and bring people from various spheres of society together.

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