Country star Jason Aldean is a dad to daughters Keeley, Kendyl and Navy, and son Memphis

As Jason Aldean has gained fame in country music, he has also expanded his family.

The “Hicktown” singer welcomed his first child Keeley in 2003 with his high-school sweetheart turned first wife Jessica Ussery. The former couple welcomed another daughter Kendyl in 2007 before calling it quits in 2013.

Two years later, Aldean married former American Idol contestant Brittany Aldean, with whom he welcomed his first son Memphis in 2017. Their daughter Navy joined the family two years later.

In November 2021, Aldean spoke with PEOPLE about climbing his way to the top of the country charts while raising a family.

“It feels good to know that for the last 16 years, I’ve had a chance to wake up and go do a job that I truly love to do,” Aldean said. “If it all went away tomorrow, I’d be like, ‘My kids are good. It’s been great.’ I got no regrets at all.”

It wasn’t always easy raising a family while constantly on the road though, and Aldean said he missed some childhood milestones because of his touring schedule.

“I don’t wanna say I’ve accomplished everything that I set out to do because I haven’t, but I’ve accomplished a lot more than what I thought I would,” Aldean told PEOPLE. “I got four beautiful kids. I got a beautiful wife and had a great career.”

Keeley Ann Williams, 21

Aldean and Ussery invited Keeley on Feb. 14, 2003.

For his oldest kid’s sweet 16, the “Enormous Green Farm vehicle” vocalist posted a birthday recognition on Instagram. “As Cheerful as I’m to see her grow up, I actually consider her that young lady moving around in front of an audience, holding her mouthpiece and imagining like she was the superstar,” he wrote in the subtitle. “I am so glad for the individual she is transforming into and, surprisingly, prouder to be her Daddy.”

In 2016, after Aldean sealed the deal with his second spouse Brittany, the rural performer got serious about Keeley’s character and said that both of his more established little girls were energized by turning out to be elder siblings.

“Keeley’s forever been a mother hen type with children, so we’d have an implicit sitter!” he told Individuals. “Also, Kendyl has forever been the younger sibling, so for her to be the older sibling, I think she’d be pretty stirred up.”

In May 2021, the proud dad shared another tribute to his eldest daughter on Instagram honoring a major milestone.

“Hard to believe this kid graduated from high school tonight. Really excited to see what the next chapter in life holds for her. Your future is what u make it, so go get em Keeley. We love you!” he wrote.

Keeley is also close with her younger sister Kendyl. In March 2022, she posted a video collage on TikTok of Kendyl and wrote, “you watched your little sister grow up and now she’s the most beautiful person and my best friend.”

Kendyl Aldean Williams, 16

Aldean welcomed Kendyl, his second child with his ex-wife Ussery, on Aug. 20, 2007. The country musician has taken his family on the road with him many times over the years and in 2021, he shared a throwback photo from a time when he brought Keeley and Kendyl along for the ride, saying it was one of his favorite photos from the road.

When Kendyl became a teenager in August 2020, the proud dad posted on Instagram to celebrate the occasion.

“Happy 13th bday to one of the coolest and sweetest kids I know,” he wrote in the caption. “It has been so cool to watch u grow up and turn into the person u are. I love u so much and couldn’t be prouder of you. Happy bday 🥜.”

Three years later, for Kendyl’s sweet 16, Aldean opened up more about her personality in an Instagram birthday tribute.

“Happy sweet 16 to one of the sweetest, kindest and most thoughtful people I know. It has truly been an honor and a blessing to be your daddy for the last 16 years,” he wrote. “We are so proud of the person you are and what you stand for. Don’t ever change that!!”

Brittany shared about the birthday party on her Instagram Stories, highlighting the braid bar, custom illustrations and personal chef on hand to celebrate Kendyl’s big day.

Memphis Aldean Williams, 6

Aldean and Brittany welcomed their first son Memphis on Dec. 1, 2017, in Nashville.

After marrying the former American Idol contestant, Aldean revealed the two were open to having children together.

“I know she would like to have at least one kid. And I’m down for that,” Aldean told PEOPLE in 2016. “I love kids and being a dad is one of the best things in the world for me. If it’s meant to happen, it will. Only time will tell.”

The two became parents after a difficult journey to conceive due to Brittany’s endometriosis. In fact, both of the couple’s children were “IVF babies” and, according to their mom, were almost “IVF twins.”

To announce the birth of Memphis, Aldean shared a family photo on Instagram of him, Brittany and their newborn 𝚋𝚊𝚋𝚢. “So blessed today to see my little man come into the world. In a year that has been a rollercoaster ride, this is what its all about,” he wrote in the caption. “I cant wait to see what life has in store for this kid.”

In 2021, Aldean joked about having one son in a family with three girls.

“I feel really sorry for Memphis, though,” he told PEOPLE, laughing. “It’s him and three sisters, so he doesn’t have a chance. I never thought I’d be having kids again at 40, but now I can’t imagine life without them. I was an only child … so having a big family was something I didn’t really have. I love having them all there and just seeing them interact.”

Navy Rome Williams, 5

Aldean and Brittany’s younger child Navy was born on Feb. 4, 2019.

“After having our son, we knew we wanted to have two kids,” the “She’s Country” singer told PEOPLE. “I have my two older daughters already, so after Memphis was born we knew we wanted to have another one pretty quick — to go ahead and knock it out and have one that was a little closer in age to him.”

Just a little over a year after Memphis was born, the couple had their 𝚋𝚊𝚋𝚢 girl.

“Today our family became complete as we welcomed our daughter Navy Rome to the world,” the country star announced on Instagram, sharing a photo of the newborn. “Born on 2/4/19 weighing 7lbs 12oz and looking identical to her older brother. So excited to watch what life has in store for this little princess.”

In August 2021, the dad of four posted a video on Instagram of Navy belting Frozen‘s “Let it Go” from her car seat while one of her older sisters giggled behind her. Aldean ended the video by turning the camera to himself and joking, “Oh no, oh no.” He captioned the cute moment, “And so it begins…… The Aldean music bug strikes again.”

The Grammy nominee, who has a tattoo of Navy’s name on his arm, posted an Instagram tribute to his youngest daughter on her third birthday. “You have the biggest smile and best personality of any kid I have ever seen,” Aldean wrote in the caption. “You are one of a kind Navy Rome. We love u so much.”