Eminem has taken shots at just about everyone over his rap career but his mom decided to launch a lawsuit against him after one song.

If you know anything about the rapper, you would know he has a complicated relationship with his mother.

Eminem has never really been shy to bring it up in his music and this hasn’t always worked out in his favor.

The rap star was threatened with a $10 million lawsuit from his mother, Debbie Nelson, after one line that featured in his song back in 1999.

Even before this song’s release, Eminem made it clear that he and his mother had a turbulent relationship since he was a child, even going as far to bring it up in press interviews.

In his 1999 hit My Name Is – which featured on his The Slim Shady LP, Eminem alleged his mom ‘smokes more dope than I do’, a line that was met with backlash from his estranged mother.

Eminem is no stranger to taken shots at people in his music (Kurt Krieger/Corbis via Getty Images)

At the time, Eminem’s manager Paul Rosenberg defended the rapper and responded to the lawsuit saying: “Eminem’s life is reflected in his music.

“Everything he has said can be verified as true. Truth is an absolute defense to a claim of defamation. This lawsuit does not come as a surprise to Eminem.

“His mother has been threatening to sue him since the success of his single ‘My Name Is’. It is merely the result of a lifelong strained relationship between him and mother.

“Regardless, it is still painful to be sued by your mother and therefore the lawsuit will only be dealt with through legal channels.”

The lawsuit was successful, in a sense but nowhere close to the lucrative conclusion she was likely hoping for.

In 2001, two years after launching the lawsuit, she was awarded $25,000, although most of it went to legal fees, leaving her with just $1,600.

Despite the loss, Eminem wasn’t one to backdown when it came to taking shots at anyone.

The lawsuit likely didn’t pan out how Debbie would have wanted (Mark Weiss/Getty Images)

After the legal battle, a year later Eminem went on to release his most scathing song about his mother, Cleaning out my Closet.

He wrote: 2002 single: “Witnessing your momma popping prescription pills in the kitchen / B****** that someone’s always going through her purse and s’s missing / Going through public housing systems, victim of Munchausen syndrome.

“My whole life I was made to believe I was sick when I wasn’t / Till I grew up, now I blew up, it makes you sick to ya stomach.”

However, Eminem seems to had improved his relationship with his mother since the early 2000s and chooses not to perform this song live at any of his concerts.

In 2014, he went as far to apologize for the release of the track in his single ‘Headlights’ and admitted that he cringes whenever he hears it now.

The pair, at least in public, appeared to have repaired their relationship and the news of Debbie Nelson’s death will likely come as quite as a blow to the rap star.

She died on 2 December from complications related to lung cancer and a rep for Eminem has confirmed the news to both People and TMZ.