Eminem, performing at the head of a swarm of bleached-blonde, look-alike Slim Shadies, took home MTV awards for both Video Of The Year and Best Male Video categories for his smash hit single, "The Real Slim Shady". The top-selling solo artist of that year, Eminem won Grammy Awards for Best Rap Album and Best Rap Solo Performance ("The Real Slim Shady"). In 2002, Eminem again courted controversy by moving up the release date of his third LP, The Eminem Show, in order to frustrate attempts by Internet pirates to distribute his album for free. Though the album won a Best Rap Album Grammy, the perennially controversial singer was booed at the MTV Video Music Awards before walking away with four trophies at New York's Radio City Music Hall. His first Hollywood movie, 8 Mile, debuted in November 2002 to rave reviews. The film's hard-charging rap hit, "Lose Yourself," scored a surprise Academy Award for Best Original Song in 2003. Beating out such mainstays as U2 and Paul Simon, it was the first Oscar ever bestowed on a hip-hop artist. The controversial rapper’s tumultuous personal life and legal struggles made headlines beginning in June 1999, less than a week after the platinum debut of The Marshall Mathers LP, when he was arrested after a brawl outside a Detroit nightclub. After pleading guilty to carrying a concealed weapon, a Michigan judge sentenced the rapper to two year's probation and ordered him to undergo counseling and drug testing. In September 1999, Eminem's mother, Debbie Mathers-Briggs, filed a $10 million lawsuit against her son. Mathers-Briggs alleged that Eminem had slandered her on The Slim Shady LP, implying she was an unstable drug user. Though she offered to settle for $2 million, Eminem rejected the settlement and the case will go to trial.

Eminem’s tempestuous relationship with his wife, Kim, whom he married in 1999 but had lived with for years before that, served as the subject of several of his songs, including “Kim,” which portrayed a violent argument between the couple. In July 2000, Kim Mathers was hospitalized after attempting suicide. A month later, Eminem filed for divorce; Kim Mathers sought $10 million and full custody of their daughter, Hailie Jade Scott, born in 1995. In a settlement, Eminem agreed not to seek custody of the young girl and Kim Mathers dropped her lawsuit. Though the couple reconciled in December of that year, their truce was shortlived, as Kim Mathers filed for divorce in early March 2001.