Getting expelled from school twice did not change his rebellious streak.
Two stints at juvenile homes also failed to set him straight.
And he was so far gone that his mother took out a Beyond Parental Control (BPC) order against him.
But two years ago, when two life-threatening illnesses - breast cancer and a stroke - struck Mr Narayanan Rankasamy's mother in the span of a week, he was jolted to his senses.
The 23-year-old told The New Paper: "I didn't want her last memory of me to be disappointing. I wanted her to be proud of me."
Mr Narayanan is now pursuing an accounting diploma at Kaplan Singapore and is set to graduate in August with flying colours.
But his road to success was far from smooth sailing.
At 15, he was led astray by bad company. He said: "I felt my friends were more important than my mum because I wasn't getting the attention I needed at home."
His mother, Mrs Sanda Govindaraju, 52, left her husband when she was five months pregnant with her son. Working as a security guard meant long hours and she often left her only child to his own devices.
She said: "I was working from 8am to 8pm. There was nobody to take care of him but what to do? I had to pay the bills."
Mr Narayanan started smoking, stealing and fighting and would return home in the wee hours.
When Mrs Sanda realised things had spiralled out of control, she applied for a BPC order against her son in 2007.
Parents can file a BPC order at the Juvenile Court for children below the age of 16 who display behavioural problems at home or school. The court can then place the child in safe custody in a juvenile home.
Mrs Sanda said: "It was a painful decision that I struggled with for months. But with BPC, at least I knew he was in safe hands."
The BPC order didn't sit well with Mr Narayanan, who felt betrayed after he was sent to the Singapore Boys' Home for two months.
Shortly after he was released on probation, Mr Narayanan resumed his bad habit - playing truant and breaking his mandatory 8pm curfew.
He was subsequently expelled from East View Secondary School in 2008. Less than a year after leaving a juvenile home, he was thrown into another, this time for two years.
But in 2010, the home kicked him out for bad behaviour and he was expelled from school a second time.
Before he enlisted for national service (NS), Mr Narayanan felt he had no direction in life, and spent his time hopping between odd jobs.
But in 2013, he found direction in the unlikeliest of places - the hospital.
In October that year, he received news that his mother was diagnosed with third-stage breast cancer and had suffered a stroke in same week.
Mr Narayanan, who was in the middle of his Basic Military Training, rushed to the hospital only to find his mother reduced to a shadow of her former self.
"To me, my mum was like Superwoman. So it was eating away at me to see her in such a weak state. I couldn't handle it."
He broke down by her hospital bed in a rare display of vulnerability.
Mrs Sanda said: "He told me, 'When you were bringing me up, I never felt the pain you went through. But to see you sick, I feel the pain now'."
Mr Narayanan frequently took leave from NS to accompany his mother on her chemotherapy and physiotherapy sessions and their relationship gradually improved.
Last year, after undergoing a mastectomy to remove her left breast and removing 20 lymph nodes, Mrs Sanda was given a clean bill of health and is now in remission.
This gave Mr Narayanan the peace of mind to enrol in an accounting course at Kaplan Singapore, where he has been scoring distinctions and credits for all his modules.
His accounting and finance lecturer, Madam Elizabeth Ng, sang his praises.
She told TNP: "He stays back after class to clarify his doubts with me and always engages in discussions. You can tell he wants to do well."
Mr Narayanan intends to pursue a part-time degree in accounting after he graduates from his course.
But Mrs Sanda, who has been unsuccessfully seeking re-employment since her recovery, is worried about the hefty school fees.
She has exhausted all her savings on her medical bills, amounting to $40,000.
"I'm so proud of him but now that he wants to study, I can't afford to let him," she said, as tears welled up.
But Mr Narayanan, who wants to become an investment banker, is more optimistic.
He said: "I'll fund my own education by working and studying at the same time.
"My mum has been taking care of me all these years.
"Now it's my turn."
Dealing with difficult children
Parents need to find the right balance between disciplining their children and overindulging them, said Dr Carol Balhetchet, a clinical psychologist and senior director for youth services at Singapore Children's Society.
She told The New Paper: "Parents should not assume that just because their children are old enough to look after themselves, they can stop worrying.
"In fact, more than ever, parents need to be both kind and firm. Keep them close, but don't suffocate them."
She advised parents to set clear and simple rules for their children to follow and stressed the importance of spending quality time with them.
"Connect with your children and get to know them.
"Then, you will be able to see the signals when trouble starts and you can intervene.
"Just by talking and sharing with them, they will gain maturity and know when to say yes and when to say no."
This article was first published on May 28, 2015. Get The New Paper for more stories.