In 1999 Mathers' mother sued him for around US$10 million over alleged slander about her in his lyrics regarding The Slim Shady LP; she won only about US$1,600 in damages in 2001.^[76]

Mathers was arrested on June 3, 2000 during an altercation at a car audio store in Royal Oak, Michigan, with Douglas Dail, where he pulled out an unloaded gun and kept it pointed at the ground.^[77] The following day, in Warren, Michigan, he allegedly saw his then wife, Kim, kiss bouncer John Guerrera in the parking lot of the Hot Rock Café so he assaulted him.^[73]^[74]^[77] He was given two years probation for both the episodes.^[78]

In the summer of 2001, Mathers' legal troubles continued, as he was given probation on weapons charges that stemmed from an argument with an employee of Psychopathic Records, giving him a fine around $2,000 as well as several hours of community service.^[79]

His group-mate Proof from D12 stated that Mathers "sobered up" in 2002 from drug and alcohol dependence.^[80] However, he did turn to zolpidem sleeping pills for relief from sleeping troubles. This caused Mathers to cancel the European leg of the Anger Management Tour in August 2005 and eventually go into rehab for treatment for a "dependency on sleep medication".^[46]^[81] In a 2009 interview with British talk-show host Jonathan Ross,
Mathers admitted that at the height of his addiction, he considered suicide, saying that "I just wasn't taking care of myself, at times I wanted to just give it up."^[82] He also confirmed that he is now sober, commenting that "[R]ap was my drug ... Then I had to resort to other things to make me feel that. Now rap's getting me high again."^[82]

Eminem alleged that he and superstar Mariah Carey had a relationship, although she denies the claim.^[83] He released a song called "Bagpipes from Baghdad"

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which calls her a "whore"; refers to her husband, Nick Cannon, as a "sucker"; and name-checks her former beau, Luis Miguel.^[84] She responded by releasing the single Obsessed, in which she sang "Why are you obsessed with me, lying that you're sexing me?"