Mindy McCready’s life didn’t always seem sadder than a country song.

Before the legal drama, controversial courtships, suicide attempts and rehab stints, she was the sexy songstress who topped the charts and made headlines both for her hits and then-taboo navel ring. She was also engaged to a TV star.

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But booze and prescription pills fueled a downward spiral that last week may have reached its most precarious point. Now her problems involve a 5-year-old boy – her son Zander.

On Tuesday, McCready, 36, removed Zander from the Florida home of her mother, Gayle Inge, who has custody of the boy, and the singer said she was willing to risk jail time over her actions. She also insisted that she was in no condition to travel after revealing she’s seven-months pregnant with twins.

Friday night, police found McCready and Zander hiding in what was believed to be the singer’s boyfriend’s house in Arkansas. By Saturday, Zander was being returned to McCready’s mother.

The recent events are the latest in a train wreck of troubles, and those who have known her are only shaking their heads.

“I hope this all works out for the best,” Dennis Rodman, who appeared with her on Celebrity Rehab with Dr. Drew, tells PEOPLE. “I really enjoyed getting to know Mindy. She is a great person.”

A Superstar in the Works

Born in Fort Meyers, Fla., McCready, 36, became famous in 1996 with her Multi-Platinum debut album Ten Thousand Angels and fashioned herself as a role model to her younger brother, telling PEOPLE in 1997 that she’d grill him about sex and call him “a pig” when he smoked cigarettes.

McCready – whose women’s anthem “Guys Do It All the Time” was instantly a smash – suffered a hardship in 1998 when she split from her fiancé, Lois & Clark: The New Adventures of Superman star Dean Cain.

She seemed to bounce back a year later when her third album, I’m Not So Tough, got solid reviews, but it wouldn’t last.

First Signs of Trouble

In 2004, she was charged with prescription drug fraud in 2004 after illegally obtaining the pain medicine OxyContin, and was sentenced to three years of supervised probation and ordered to perform 200 hours of community service.

“It was a stupid thing to do,” she later said, claiming her purchase was for a friend. “I am not a drug addict.”

In 2005, the star was arrested again and charged with DUI and driving on a suspended license.

“I had not had a drink for four or five hours prior,” she said. “I was driving home a drunk driver.”

A few days later, her ex-boyfriend William McKnight was charged with attempted murder and aggravated burglary after allegedly breaking into her home and beating her up.

Covered in bruises, she testified against him in court, claiming he punched her, choked her and hit her head against a headboard.

“It’s a bad situation,” McCready told PEOPLE at the time. “I’m in a lot of pain, but I will get through it.”

Problems Only Worsen

She vowed to move forward, but just weeks later, McCready was charged in Arizona with identity theft, unlawful imprisonment and hindering prosecution, then hospitalized for apparently attempting suicide by drug overdose.

By her side was McKnight, telling authorities she wrote a four-page suicide note before consuming massive alcohol and ingesting several different substances. McCready left the hospital and went back to him.

“We’re very much in love,” McKnight told PEOPLE.

But in September 2005, McCready attempted apparent suicide again, reportedly taking 30 antidepressants while pregnant with McKnight’s child.

Two years later, she served a several-month jail sentence, stemming from a probation violation after resisting arrest and committing battery during an argument with her mother.

Then came the strangest twist: Yankees pitcher Roger Clemens acknowledged making mistakes in his personal life after McCready claimed they had an affair. The singer alleges she was only 15 when they met.

It seemed like nothing now reported about McCready was positive, and along the way she lost custody of her child to her mother.

She headed back to rehab for undisclosed reasons following a trip to the emergency room and served more jail time for a probation violation.

Reality Show

She kept claiming that she was making strides to “put all of this behind me,” but she soon wound up back in the hospital for another suicide attempt.

By 2009, her problems became fodder for a reality show. McCready joined Mackenzie Phillips, Heidi Fleiss and Rodman on season three of VH1’s Celebrity Rehab with Dr. Drew. McCready infamously suffered from a seizure that was documented on the series, mid-detox.

Her March 2010 album Still Standing, her first in eight years, documented her downfall but didn’t save her.

Two months after the release, McCready was hospitalized for a mystery ailment. There was discrepancy over whether she overdosed on prescription pills or reacted badly.

Now she’s facing the possibility of jail time for not returning her son to his legal guardians. Her ex, who was there during some of the darkest times, is hoping there is some silver lining.