Nelson, who died Tuesday of complications from cancer, endured a longstanding feud with the famous rapper and even sued him for defamation.

Over the course of his nearly three-decade career, rapper Eminem has cited elements of his personal and professional life throughout his hit songs. This has frequently included his tumultuous relationship with his estranged mother, Debbie Nelson.

Unfortunately, any hope of a confirmed reconciliation between the singer and his mother is now gone, as People reported that Nelson died Monday at age 69 of complications from advanced lung cancer.

Eminem, now 52, was often candid about the animosity between himself and his mother. He alleged Nelson had a drug addiction and behaved abusively through interviews and his own song lyrics. The pair even went to court over the claims, which Nelson denied. Despite this, both hinted that a reconnection was possible.

Here’s what you need to know about the singer’s strained relationship with Nelson and how it evolved over time.

Nelson raised Eminem on her own

As Biography previously reported, Nelson gave birth to Eminem—whose real name is Marshall Bruce Mathers III—on October 17, 1972, in St. Joseph, Missouri. She was only 18 at the time.

Nelson raised him and his younger half-brother, Nathan, on her own after Eminem’s father left the family. She struggled to keep steady employment, meaning the family frequently moved between Missouri and Detroit. Young Marshall struggled to make friends and maintain his grades as he changed schools. Ultimately, he failed the ninth grade three times and dropped out of school at age 17.

By this point, Marshall was an aspiring rapper who adopted the stage name M&M, which he later changed to the phonetic spelling we all know. After signing with Interscope Records in 1997, the singer finally had an outlet to channel his creativity—and apparent resentment toward Nelson.

Eminem referenced Nelson in a number of his songs

As he gained fame, Eninem didn’t shy away from criticizing Nelson and his upbringing. In a 1999 interview with Rolling Stone, he accused her of stealing paychecks, frequently kicking him out of their house, and abusing pills and drugs that triggered mood swings. Nelson maintained she never used drugs.

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Eminem’s first hit song included an attack on his mother, who later won a defamation lawsuit against the rapper.

The singer’s claims soon spilled over into his music. In his breakout song “My Name Is” Eminem directly references Nelson and her alleged drug use. “I just found out my mom does more dope than I do,” he says in one line from the 1999 hit. Three years later in “Cleanin’ Out My Closet,” Eminem hinted at further abuse by Nelson and even alleged he was a victim of Munchausen syndrome.

Not surprisingly, the singer’s public claims deeply troubled Nelson, leading to a legal standoff that drove the mother and son even further apart.

Nelson sued Eminem for $10 million

In 1999, Nelson filed a defamation lawsuit against Eminem seeking at least $10 million in damages. According to Rolling Stone, the suit alleged he slandered her in multiple broadcast and print interviews by suggesting she abused drugs and was unstable.

The rapper’s lawyer, Paul Rosenberg, described the suit as “merely the result of a lifelong strained relationship between [Eminem] and mother” and asserted that all of the singer’s claims could be verified as true.

A judge in Michigan’s Macomb County District Court ultimately ruled in Nelson’s favor for a settlement of $25,000, ABC News reported. However, she was only entitled to $1,600 after legal fees.

Following the court saga, Nelson released her own diss track called “Dear Marshall (An Open Letter to Eminem),” reflecting on her own mistakes and son’s behavior in the lyrics: “Will the real Marshall Mathers please stand up / And take responsibility for his actions?”

According to USA Today, Nelson also hoped to appear in the 2002 semi-autobiographical movie 8 Mile, starring Eminem as fictional rapper Jimmy Smith Jr. The role of Smith’s mother ultimately went to actor Kim Basinger.

It’s unknown if Nelson and Eminem reconciled

Despite their acrimonious past, both Nelson and Eminem eventually hinted at a willingness to reconcile. In 2008, Nelson published her memoir My Son Marshall, My Son Eminem, in which she spoke candidly about her relationship with the singer. “In my heart I know Marshall still loves me. He’s just confused,” she wrote.

Five years later, Eminem seemingly apologized to his mother with the single “Headlights,” in which he expressed regret over his public commentary about their relationship and Nelson’s lack of relationships with his own children.

More recently, Nelson congratulated Eminem on his 2022 induction to the Rock & Roll Hall of Fame. “I love you very much. I knew you’d get there. It’s been a long ride. I’m very, very proud of you,” she wrote on social media.

In Touch Weekly reported this past September that Eminem wasn’t on speaking terms with his mother and hadn’t visited her in Missouri amid her cancer battle. However, a source told the outlet the singer did support Nelson financially.

While it’s not known if the pair mended their relationship prior to Nelson’s death, there is no denying their rift played a crucial role in Eminem’s career to say nothing of his personal life.