Eminem has built his career around being an angry controversial rapper. He’s also spent most of his career fighting legal battles. The inside of a courtroom is no stranger to the artist whose legal name is Marshall Mathers, and over the years, it seems he’s spent more time with his lawyers than in the recording studio. Question is, how big of a hole has it burned in his pocket?

It started in

1999

when Eminem dropped The Slim Shady LP on Aftermath/Interscope Records. He laced his raps with raw and unfiltered emotion as he slandered the hell out of his mother Debbie Mathers, and in return she sued him for around $10 million. The case lasted till 2001, and she was awarded a mere US $1,600 in damages.

Then in

2000

, the no-BS rapper whipped out an unloaded gun during an altercation at a car audio store in Royal Oak, Michigan, and was arrested on the spot. The following day in a different city, Warren, Michigan, Eminem reportedly saw his then-wife Kimberly Scott, kiss a bouncer in the Hot Rock Cafe parking area and after assaulting the bouncer named John Guerrera, the rapper was arrested again. Taking reality and slicing it up into comedy, Em re-enacted the parking lot assault in a skit on his 2000 release The Eminem Show; the track was called “The Kiss (Skit)”. He was charged for both offences with possession of a concealed weapon and assault. He pleaded guilty to both charges and was given two years probation.

A few months later, Scott slashed her wrists in an attempted suicide. Almost in celebratory fashion, Eminem went on to release a song called “Kim”, and she sued him for defamation. The track starts off with Eminem talking sweetly to their daughter Hailie, and ends with Kim’s throat being slit and him pulling her into the trunk of the car. This was only the beginning of the graphic images he’d go on to paint of his toxic relationship with the mother of his daughter.

Eminem became a bad boy rapper almost overnight, and his raps painted a self-destructing time-bomb waiting to go off. The troubled rapper lived up to the hype, and continued to cement his already crumbling relationship with the law.

That same year, Mathers was scheduled to perform in Toronto’s Skydome, but an Ontario Attorney General opened a case that the rapper not be allowed entry into Canada. Attorney General Jim Flaherty’s claims were reportedly based on the vulgarity in one of Em’s songs titled “Kill Me”. Flaherty said: “I personally don’t want anyone coming to Canada who will come here and advocate violence against women.” An MPP at the time, Michael Bryant went as far as to say that the rapper should be charged with hate crimes for advocating violence against women, as can be heard in his lyrics. The parties went back and forth trying to deny him entry into the state, but in Eminem’s favour, the Toronto concert went ahead as planned.

At this point, Mathers’ had just released his third LP, titled Marshall Mathers under the Aftermath/Interscope Records label, and his hot property stakes were rising. He was earning his stripes alongside some of the best rappers in the game, and his name was starting roll off of Hip Hop stans’ tongues. So you’d think he’d want to steer clear from controversy? Nah. Not Eminem.

In

2001

he was sued by a former schoolmate, sanitation worker D’Angelo Bailey, who claimed that the rapper invaded his privacy and tarnished his reputation. Eminem was accused of reportedly publicizing unreasonable information on his track “Brain Damage” that put Bailey under false light. Bailey sought $1 million in damages as a result of Eminem’s raps: “I was harassed daily by this fat kid named DeAngelo Bailey. An eighth-grader who acted obnoxious, ’cause his father boxes. So every day he’d shove me into the lockers.” In 2003 the charges against Mathers was dismissed in court.

Then Eminem got into an argument with an employee of Psychopathic Records in June that year, and he was sentenced to one year probation on weapon charges. He was ordered a fine of $2,000 including community service.

As if “Kill Me” hadn’t created enough drama in his life between him and Kim, in March

2002

, a French Jazz pianist Jacques Loussier claimed that the beat was stolen from his jazz fusion song “Pulsion”, and he filed a $10 million lawsuit against Eminem and his producer Dr. Dre. Although a trial date was set for June, 2004, the case was later settled for an undisclosed amount.

In

late 2002

, a feud between The Source’s co-owner at the time, rapper Raymond Scott aka Benzino, started heating up. Mathers’ started dissing The Source because he thought his Marshall Mathers LP was worthy of the highly acclaimed 5 Mics and Benzino retaliated making claims that Em was in the game to discredit black and Latino artists’ contributions to Hip Hop. This sparked a battle of diss records versus diss records, which resulted in some personal vindictive raps. Eminem went on to sue The Source for defamation and copyright infringement. The federal courts passed an injunction to limit the distribution of tapes that The Source had dug up of Eminem making racial slurs against Blacks and women. This injunction was ignored by the magazine, and they were found in contempt of court. As a result, the magazine was forced to pay Eminem and his label, Shady Records an undisclosed amount in compensation. By the time both parties were preparing to go to trial for the copyright infringement case, Em withdrew, stating he no longer had beef with The Source.

So what do you do when you’re peaking as a rapper, and you’ve literally got all eyes on you from everyone in the rap game – rappers and fans alike? You get the attention of the United States Secret Service. Well that’s what Eminem did anyway.

In December,

2003

, the USSS made it public that they were enquiring into allegations that Eminem was a threat to the President of the United States at the time, George W. Bush. See, they got hold of an unreleased song called “We As Americans” that was circulating the streets. The urgency was in the raps: “Fuck money, I don’t rap for dead presidents. I’d rather see the president dead, it’s never been said but I set precedents”. Later in a video called “Mosh”, Eminem referenced several news clips relating to the enquiry, including references to some of Bush’s unfortunate moments as the President of the United States of America.

Late

2003 – 2004

saw Apple Inc. and Eminem head to court over his song “Lose Yourself” that was used in a TV commercial for the Apple iTunes music store that appeared on MTV for three months. The ad however featured a 10-year old rapping the lyrics to the track that won Em an Oscar.

By this time, Eminem had everyone tugging at his pockets for a piece of the pie; he was playing in the big league, and family members were in the forefront. In

2005

, Eminem was sued by his aunt and uncle, Jack and Betty Schmitt. As the story goes, the rapper promised them a $350,000 house, and an allowance to maintain the property, but apparently Em kept the property in his name and tried to evict them; another scenario of “mo money mo problems”.

In

2007

, Eminem and Apple Inc. came head to head again. The Detroit rapper and his music publishing company Eight Mile Style LLC, alongside Martin Affiliated LLC filed a multi-million-dollar lawsuit against iTunes operator for alleged copyright violations, and Aftermath Entertainment. The claim with Aftermath was that they did not negotiate an appropriate deal with Apple for his digital downloads. The complaint filed stated that Apple allegedly paid a portion of the revenue it accumulated from Eminem’s downloads to label giants Universal Music Group; but the downloads were never authorized. The claim with Apple was settled shortly after the trial began out of court, for an undisclosed sum. It was only in July 2010 that the United States Court of Appeals for the Ninth Circuit ruled that F.B.T. Productions and Eminem were owed a royalty of 50% of the net revenue.

The latest of Eminem’s run-ins with the law is the $9 million lawsuit over a Chrysler advertisement. The claim alleges that Eminem intentionally used the intellectual property of last years’ most popular Super Bowl ads, and the plaintiff is seeking millions in damages. According to a popular Hip Hop website, a New York man filed the $9 million lawsuit on

January 2012

. The plaintiff, Stephen Lee Pieck reportedly claims that in the company of Christina Aguilera and her now ex-husband, he pitched the idea for Chrysler’s “Born of Fire” two-minute ad telephonically to Em. In a recent media report, Pieck was quoted saying: “I designed every aspect of the commercial and the commercial was stolen from me. In addition, I did not receive compensation in monetary terms for the work I did.” This enquiry is still underway.

Over a time-span of 13 years, Eminem has had at least one major lawsuit per year. And when it wasn’t a new lawsuit being filed by the Detroit rapper, or filed against him, his legal woes have overshadowed the music to an extent. Although the damages he has settled have been a small portion, his legal fees cover the bulk of these expenditures. And no matter how much cash you’re raking in from performances, album and digital sales, this average amount of $1000 per consultation for an Entertainment lawyer can leave a dent in any rappers’ pocket.

There’s no calculated figure that can be put on Eminem’s legal troubles, but over 13 years, an approximate $4,745,000 just about covers his legal representation for 365 days a year, and whatever damages and fines was due to him, are separate. Goes to show, it’s all fun and games till the lawyers bill ends up on your desk. But in Eminem’s case, and with his latest lawsuit making headlines, it seems he’s got a lot more cash to play around with.