
In the five-part documentary series Luke Bryan: My Dirt Road Diary, country music superstar Luke Bryan opens up about his life, including the tragic deaths of his brother, sister, and brother-in-law. Bryan's brother-in-law, Ben Lee Cheshire, was the husband of Bryan's sister, Kelly, who died suddenly in 2007. Cheshire himself passed away from a heart attack in 2014, leaving behind three children with Kelly. Bryan and his wife, Caroline, took in their nieces and nephew, providing a stable family environment despite their own grief. In the documentary, Bryan reflects on his relationship with his brother-in-law and the impact of his loss, showcasing his genuine, charismatic, and loyal personality.
| Characteristics | Values |
|---|---|
| Name | Ben Lee Cheshire |
| Relationship | Brother-in-law |
| Year of Death | 2014 |
| Cause of Death | Heart attack |
| Relationship with Luke Bryan | Known each other since Luke was 7 or 8 years old |
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What You'll Learn
- Luke Bryan's brother-in-law, Ben Lee Cheshire, died of a heart attack
- Bryan and his wife adopted his brother-in-law's three children
- Bryan's brother-in-law was like a brother to him
- Ben Lee Cheshire was the husband of Bryan's sister, Kelly
- Bryan's documentary, 'My Dirt Road Diary', explores his family tragedies

Luke Bryan's brother-in-law, Ben Lee Cheshire, died of a heart attack
Country music star Luke Bryan has suffered unimaginable losses in his life, including the deaths of his brother, sister, and brother-in-law. In his recent IMDb TV docuseries, "Luke Bryan: My Dirt Road Diary," Bryan opens up about his grief and the impact of these tragedies on his life. One of the tragedies he reflects on is the loss of his brother-in-law, Ben Lee Cheshire, who died of a heart attack.
Ben Lee Cheshire was the husband of Bryan's sister, Kelly Cheshire. Kelly passed away suddenly in 2007, and just seven years later, in 2014, Cheshire also passed away. Bryan described Cheshire as not just his brother-in-law, but his brother, as he had been in his life since he was seven or eight years old. The loss of Cheshire was yet another devastating blow to Bryan and his family, coming just years after the death of his sister.
In his docuseries and in interviews, Bryan candidly discusses his anxiety and grief following these losses. He and his wife, Caroline, took in Cheshire and Kelly's three children: Jordan, Kris, and Til. Bryan shared his worries about how viewers at home would react to hearing about the tragedies in his life, but he also expressed his hope that by sharing his story, he could help others who have gone through similar experiences.
The couple's decision to adopt their nieces and nephew was an easy one, as Caroline shared in a 2017 interview on Good Morning America. Bryan's music has also been influenced by these losses, with songs like "Songs You Never Heard," which he wrote for his late brother. Bryan's faith in God has helped him through these difficult times, and he continues to find strength in his family and his successful music career.
The losses of his brother, sister, and brother-in-law have undoubtedly shaped Bryan's life and perspective. By openly discussing his grief and anxiety, Bryan has not only worked through his own emotions but has also connected with fans who may be going through similar struggles.
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Bryan and his wife adopted his brother-in-law's three children
Country music star Luke Bryan has suffered unimaginable losses in his life, including the deaths of his brother, sister, and brother-in-law. In the midst of these tragedies, Bryan and his wife, Caroline, made the selfless decision to adopt his brother-in-law's three children, taking on the role of parents to their nieces and nephew. This act of love and dedication showcases the couple's unwavering commitment to family.
Bryan's older brother, Chris, passed away in a car accident in 1996, just as the singer's career was taking off. Then, in 2007, Bryan's sister, Kelly, died suddenly. Kelly's husband, Ben Lee Cheshire, died of a heart attack in 2014, leaving behind their three children: Jordan, Kris, and Til.
At the time of their parents' deaths, Jordan was 20, Kris was 16, and Til was 13. Without hesitation, Bryan and Caroline welcomed them into their home and became their legal guardians. The couple already had two children of their own, sons Thomas and Tatum, and Caroline had been the breadwinner for many years while Bryan pursued his music career. Despite the challenges, they came together as a family to support and care for these grieving children.
In an interview, Bryan shared his feelings about taking on such a significant responsibility: “Obviously my nieces and nephew, they didn’t ask for this. Their life was amazing before Caroline and I took a more prominent role, even after losing their mother. Now my focus is trying to do what we can to help them.” Bryan also acknowledged the anxiety and hesitancy he felt when speaking about these tragic events, aware that people might wonder why so much tragedy had befallen his life.
Despite the heartache and challenges, Bryan and Caroline's decision to adopt his brother-in-law's children is a testament to their strength and love for their family. By providing a stable and loving home for Jordan, Kris, and Til, they have helped them navigate the loss of their parents and offered them a chance for a brighter future. This selfless act demonstrates the power of family bonds and the capacity for resilience in the face of adversity.
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Bryan's brother-in-law was like a brother to him
Country music star Luke Bryan has endured multiple family tragedies. In the documentary "Luke Bryan: My Dirt Road Diary," Bryan opens up about the grief he suffered after the deaths of his siblings and brother-in-law, Ben Lee Cheshire, who was married to Bryan's sister Kelly. Cheshire's death hit Bryan hard, as he considered him a brother.
Ben Lee Cheshire was the husband of Kelly, Bryan's sister. Bryan's sister Kelly and Ben Lee Cheshire had three children together: Jordan, Kris, and Til. After Kelly's sudden death in 2007, Bryan and his wife, Caroline, took in their nieces and nephew, adopting them into their family. Bryan and his brother-in-law had a close relationship, with Bryan stating that Cheshire had been in his life since he was seven or eight years old.
The country singer described his brother-in-law's death as a significant loss, expressing anxiety about sharing such tragic aspects of his life. Bryan's brother-in-law, Ben Lee Cheshire, died of a heart attack in 2014, seven years after Kelly's death. This loss added to the grief Bryan was already processing from the deaths of his brother, sister, and niece.
Bryan's brother-in-law played a significant role in his life, and his death was yet another tragedy that the singer had to navigate. In the documentary, Bryan candidly discusses his feelings of anxiety and the impact of these losses on his life and career. He also reflects on how his faith in God helped him through these difficult times.
The documentary "Luke Bryan: My Dirt Road Diary" provides a raw and emotional insight into Bryan's life, showcasing his resilience and determination to honour his late brother-in-law's memory by supporting his children and continuing to succeed in his music career.
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Ben Lee Cheshire was the husband of Bryan's sister, Kelly
Country music star Luke Bryan has suffered unimaginable losses in his life, including the deaths of his brother, sister, and brother-in-law. In the documentary "Luke Bryan: My Dirt Road Diary," Bryan opens up about his grief and the impact of these tragedies on his life. One of the tragic figures in his life is Ben Lee Cheshire, who was the husband of Bryan's sister, Kelly.
Kelly Bryan, who was married to Ben Lee Cheshire, passed away suddenly in 2007. Her death deeply affected Luke Bryan, and it occurred around the time when he was achieving stardom in the country music industry. Kelly's death was followed by the passing of her husband, Ben Lee Cheshire, just a few years later in 2014. Cheshire died of a heart attack, leaving behind three children with Kelly.
Ben Lee Cheshire was not just Bryan's brother-in-law but also a close friend and confidante. Bryan shared that Cheshire had been in his life since he was seven or eight years old. The two had a strong bond, and Cheshire was someone Bryan could rely on. In an interview, Bryan expressed his anxiety about sharing such tragic aspects of his life with the public but acknowledged that it might help others who have gone through similar experiences.
Following the deaths of Kelly and Ben Lee Cheshire, Bryan and his wife, Caroline, took in their three children: Jordan, Kris, and Til. The couple adopted the children and provided them with a stable family environment. Bryan and Caroline's decision to care for their nieces and nephew showcases their commitment to family and their willingness to support those impacted by tragedy.
The losses of his brother, sister, and brother-in-law, Ben Lee Cheshire, had a profound impact on Luke Bryan's life and career. Through his documentary and interviews, Bryan has opened up about his grief and the ways he has coped with these tragedies. By sharing his story, Bryan has connected with fans who have experienced similar losses and offered them a sense of comfort and inspiration.
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Bryan's documentary, 'My Dirt Road Diary', explores his family tragedies
Country music star Luke Bryan has faced multiple family tragedies. In his documentary, 'My Dirt Road Diary', Bryan opens up about the grief he suffered after losing his brother, sister, and brother-in-law. Bryan's older brother, Chris, died in a car accident in 1996, just as the singer was about to move from Leesburg, Georgia, to Nashville to pursue his music career. This tragic event caused Bryan to delay his move and stay with his family as they grieved.
In 2007, Bryan's sister, Kelly, passed away suddenly at the age of 39. Her death was followed by that of her husband, Ben Lee Cheshire, who died of a heart attack in 2014. Bryan and his wife, Caroline, took in their three children: Jordan, Kris, and Til. In an interview, Bryan reflected on his anxiety about sharing such tragic aspects of his life, but he wanted to help fans heal from their own losses.
Bryan's documentary, 'My Dirt Road Diary', premiered on IMDb TV and provided an honest account of the singer's life. In it, he explores his grief and the impact of these losses on his life and career. Bryan also shared his new single, "Songs You Never Heard," which he wrote for his late brother. The song evoked emotions from those close to him and helped him connect with fans who had experienced similar tragedies.
The country superstar has faced unimaginable lows while navigating a successful career. Bryan's faith in God has helped him through these challenging times, and he has found solace in music and the support of his wife. By sharing his story, Bryan aims to help others going through similar struggles and honour the memory of his late siblings and brother-in-law.
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Frequently asked questions
Ben Lee Cheshire was Luke Bryan's brother-in-law and sister Kelly's husband.
Ben Lee Cheshire died of a heart attack in 2014.
Yes, Luke Bryan lost his brother, Chris, in a car accident in 1996, and his sister, Kelly, in 2007.
Yes, Luke Bryan and his wife, Caroline, have two children, Thomas and Tatum.
Yes, Luke Bryan and his wife, Caroline, took in their nieces, Jordan and Kris, and their nephew, Til, after the deaths of their parents, Kelly and Ben Lee Cheshire.


































