From singing "Jack & Diane" to spilling on John Mellencamp and Meg Ryan.
The singer-songwriter recently revealed where he stands with the Sleepless in Seattle actress following the end of their decade-long relationship in 2019.
"I love Meg Ryan," Mellencamp told Esquire in an interview published June 13. "I went with her for ten years. She doesn't love me so much. She's a great girl. I'm just a s--tty boyfriend."
Looking back at their time together, he also shared a memory from the early days of their romance.
"Meg Ryan had just come out of her shell; I had just come out of my shell," the musician recalled. "We started dating. And we decided to do things on our own instead of having people do stuff for us. We were so f--king lost. We didn't know how to do anything. I've never checked out of a hotel by myself."
Mellencamp then remembered one particularly funny moment when they tried to buy some groceries.
"Her and I went to a grocery store, and they wanted our credit card, and we looked at each other and said, 'Here it is,' and they said, 'No, you've got to put it in this thing,' and we went, 'Then what happens?'" he continued. "We laughed at how stupid we are, so hard we cried. I think she's learned how to do everything, and I've learned how to do nothing."
Mellencamp, 71, and Ryan, 61, initially dated for three years before they broke up in 2014, with him suggesting long-distance took a toll on their relationship.
"She was just an angel sent to me at the right time," he said on SiriusXM's The Howard Stern Show later that year. "We tried to have a relationship for three years long distance. We'll see what happens."
While the "Hurts So Good" artist and the You've Got Mail star briefly sparked reconciliation rumors after they were spotted together post-split, he went on to date Christie Brinkley from 2015 to 2016.
And while Ryan and Mellencamp may have experienced some ups and downs over the years—with him telling Howard Stern in 2017 that she "hates me to death"—they later got back together, with her confirming their engagement on Instagram in 2018. However, they parted ways again the following year.
Still, the rocker has plenty of love in his life from family.
"Daughters love their dad. They call me every day. The boys are different," Mellencamp—who has five children, including The Real Housewives of Beverly Hills alum Teddi Mellencamp—told Esquire, later adding, "I don't know how many grandkids I have. A lot."