11/07/2013 10:06 am ET Updated Nov 11, 2013

Michael Bolton On His 'Darkest Hours' Before Fame (VIDEO)

Michael Bolton landed his first record deal with Epic Records at age 15, but it took nearly two decades for him to strike it big. When "Oprah: Where Are They Now?" caught up with the now 60-year-old singer/songwriter, he opened up about how he struggled to get by in those early years.

Bolton says when his band Joy received their first deal from Epic Records, he didn't hesitate to throw himself into the music business. "I left school with my parents' blessing because I had record industry people saying, 'You've got what it takes, you've got the element in your voice that our industry thrives from,'" he says.

If he stuck with it, they told him he would make it. "I didn't realize they meant stick to it 18 years," Bolton says. "I learned that just because you have a record deal doesn't mean you've made it, doesn't mean you and your family are going to be okay."

In his early 20s, Bolton married Maureen McGuire and they had three daughters. "Without any doubt the toughest part was having three young daughters and a wife, and I know my rent check may bounce -- and in certain cases, at certain times it did," Bolton says.

He remembers getting calls from his landlord asking for rent money. "And I would apologize," Bolton says. "This kind of thing went on in what I would say were the darkest hours of my attempt to make it. I know that feeling of not knowing where the next rent check coming from and where dinner is coming from. I know that feeling."

"Oprah: Where Are They Now?" airs Sundays at 10 p.m. ET on OWN.

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