10 Slept-On Eminem Freestyles, Ranked

These days, Eminem is regarded as one of the greatest rappers of all time, but it was not always like that. He started out at the age of 14, competing in freestyle rap contests, sneaking into his friend Proof’s high school to hone his craft. He continued to cut his teeth during open mics at the Hip-Hop Shop, long considered the starting point for any aspiring Detroit rapper. By the mid-1990s, Em had become a known name around the city, even with local DJs rejecting his debut album Infinite, in large part because of what he’d done on the freestyle and battle rap circuits. 

Of course, Eminem’s excellence as a freestyle rapper starts with the time he spent as a kid learning how to put together words and the reps he put in. But it also comes from his ability to focus on different rhyme schemes and the wide vocabulary he built. Moreover, his freestyles are original to him, even with his time studying his peers and how they rapped. Em has a style that is unmistakably Em, and it shines through in each of the performances on this list.

He has delivered some of the most famous (and infamous) freestyles ever. There's the cypher with Black Thought and Yasiin Bey at the 2009 BET Awards. And who could forget his Donald Trump-dissing verse at the 2017 BET Hip-Hop Awards? Those will not be discussed here. Instead, we are ranking 10 of Eminem’s more underrated TV outings and radio freestyles.

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Eminem’s 2002 appearance on Rap City is a fun, low-stakes time with the other members of D12. This freestyle, filmed in Em’s basement, also includes verses from Proof and Kon Artis. These verses are more playful than anything else, and a clear display of the fluidity of their chemistry. 

Halfway through the cypher, Bizarre grabs the microphone and acts like he’s going to say something. He passes it to Eminem, who jokingly says “I’m not sure if I can follow that” before launching into his verse. Em’s verse doesn’t seem like he’s trying to wow an audience with a bunch of bars. Instead, he delivers a verse that plays it safe in favor of a more agile-sounding flow. He quips that he has “start-s**titis,” which is accurate given his long list of feuds. The other members of D12 do not rap here. Instead, it's an effective three-man weave from a more subdued Em than usual and two of D12’s strongest non-Em rappers.

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For years, one of the persisting myths about the early days of Eminem’s career was that Dr. Dre was listening to Sway & King Tech’s The Wake Up Show, heard this freestyle, and rushed to sign him. That is not quite how it played out for Em. He was already on Dre’s radar by this point. Then-CEO of Interscope Jimmy Iovine had already played Dre his demo tape. Still, it is easy to see why the story remains so prominent for as long as it has. 

Em rhymes over The Notorious B.I.G’s “Kick in the Door” for two full minutes. He opens the first verse with a series of lines that have not aged well at all. He closes with “foul style galore, verbal cow manure / comin’ together like an eyebrow on Al. B Sure,” which got loud laughter from those in the room. The second verse is more of Em’s darkly humorous raps. Toward the end, the lyrics take on a much more violent edge. It feels like an early take on what would later become the star-making Slim Shady character. Based on the reactions he got in the room from Sway and Tech, it was early proof that the twisted sense of humor that would help break Eminem through to the mainstream would eventually catch on if given the chance to.

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In May 2000, Eminem dropped The Marshall Mathers LP, and he hit up BET’s Rap City as part of his press run. During his Rap City appearance, he delivered a freestyle, since dubbed “Keepin' It Raw” by fans because of the verse’s first line (“I’m keeping it raw, Illegal like Malik and Jamal”). The internal rhymes are impressive. He keeps a 4-syllable scheme throughout the entire verse, and does not deliver any filler bars, packing something into every line. “I got ya little son, you'll be receivin' a call / You lucky this little punks still breathin' at all / F**k the world, this how I get even at y'all / Pop shit, get rolled up and leave in a ball,” he raps on the first part of the verse. He maintains the “e” and “aw” scheme for the entire verse, which clocks in at barely over a minute. It’s a focused effort with an appropriate fanmade title. The freestyle is a staggering display of raw talent by one of hip-hop’s premier technicians.

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Eminem made the rounds on college radio stations before making it to the big time. His appearance on Baruch College’s WBMB is true to Em’s roots as a rapper. For nearly eight minutes, he goes over beats from artists like Diamond D. Em drops funny, violent, and occasionally downright nonsensical bars for the entire runtime.

“Killing you off slowly, like Roberta Flack I've never heard of wack / MCs that try to step to me, I'll break your verta-back, or vertebrae, increase the murder rates in 79 states,” he raps. It served as an early look into some of the comically sadistic, almost Joker-like subject matter that would dominate Em’s output for the early part of his commercial career. It is a performance that is not quite as immediately great as his radio appearances the following year or some of the TV appearances he made later in his career. Even though he’s unwaveringly confident in his abilities, he had not yet fully figured out who “Eminem” was. If anything, it’s a rough draft (hence him later repurposing the freestyle's third verse on “As The World Turns”). Despite that, it’s a strong showcase of untapped potential clearly on the cusp of a breakthrough.

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Eminem and Royce da 5’9 first met each other in December 1997, quickly becoming friends and frequent musical collaborators. This appearance, another college radio session, took place on WNYU, New York University’s student-run radio station, in 1998, ahead of the release of The Slim Shady LP. 

Em’s first verse later became the one he used for the Bad Meets Evil cut “Scary Movies,” which dropped later that year. It’s a wide-ranging and topical verse. He references the Bill Clinton and Monica Lewinsky scandal, his loss to Kid Rock on MTV’s Celebrity Deathmatch, and calls himself  “sicker than a 2Pac dedication to Biggie.” Royce delivers battle-type bars that feel very reminiscent of something from a Wu-Tang album. He does well to play the gruffer foil to the cartoonish delivery of Slim Shady. 

At his best, one of Eminem’s strengths as a rapper was his ability to unload a topical verse about things happening around him. The deaths of 2Pac and Biggie in late 1996 and early 1997 were massively affecting hip-hop. The Clinton-Lewinsky scandal was the biggest news story in the United States in 1998. Em’s ability to have his finger on the pulse and keep his verses relevant was necessary to his early success, and that was no different here.

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This freestyle, which originally took place on MTV News in 1999, is a shining example of Eminem’s quick wit. The premise is simple: Em’s manager Paul Rosenberg gives him a word and Em has to incorporate it into a line in the verse. Em fits words like “excrement,” “Vaseline,” “Nostradamus,” and “taxicab” into a 4-minute barrage of witty bars (i.e.“with a taxicab, I'll smack a b***h with a Maxi pad / where we going? Don't ask me dad.). 

Rosenberg also brings up Mark Wahlberg and Em responds by calling him a “small turd.” He makes light of their awkward showing on TRL where Em stabbed at Marky Mark & The Funky Bunch after specific directions against bringing up Wahlberg’s old rap group. It’s a verse that shows how well Eminem can think on his feet. However, it is not quite as hard-hitting as some of the other freestyles from this point of his career. But it is inventive. The quick ability to adapt as Rosenberg throws whatever words or phrases he can think of across a variety of topics that have nothing to do with each other shows why Eminem is one of the most gifted freestyle rappers of his era.

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In the late 1990s and early 2000s, Eminem was a frequent guest on Tim Westwood’s BBC Radio 1 show. His 2009 appearance on the show is comfortably his most popular, amassing over 82 million YouTube views since its release. In 1999, both Eminem and Proof appeared on Westwood’s Radio 1 show. That episode also included a guest appearance by Marley Marl, the legendary producer and DJ who helped shape the sound of early hip-hop thanks to his work with rappers like MC Shan and Big Daddy Kane. Eminem and Proof sitting next to Marley Marl was a massive endorsement, and they made the most of it.

The two of them trade bars for almost eight minutes, discussing their international appeal, shoutouts to D12, and a lot of posturing about being the best in the game (Em raps “Like the Energizer bunny, that's why it's funny / When rappers try to step to me and try to step to me, and battle me for money” halfway through his third verse). Em also repeatedly makes fun of the "no cursing" directive they received before they started rapping. He “slips” halfway through his first verse, asking “did I say that or did I think it?” when he does.

By the end, Marley Marl is fully on board with the duo, and praises them for their appearance on the show. For Eminem, his radio and TV spots in 1999 and 2000 were all about showing that he belonged in hip-hop. His verses on Westwood’s show and elsewhere showed that he was not a gimmicky rapper, and that he was actually someone to take seriously on the mic.

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Eminem had lived a thousand lives by 2009. After releasing Encore in 2004 and the greatest hits compilation Curtain Call the following year, he seemed ready to retire. Ending it there would have concluded one of the most successful periods in the history of popular music by surprise. Following a life-changing methadone overdose at the end of 2007 that resulted in Em going to rehab and getting sober, he started working on new music. The result was Relapse, released in May 2009. It marked the first full album of new tracks by him in almost five years. To promote the album, Em returned to Rap City alongside Denaun Porter and 50 Cent (who served as a hype man) to deliver an emphatic comeback statement.

Em raps about Angelina Jolie and Mariah Carey. He refers to himself as Tommy Mottola, the music mogul and Mariah’s ex-husband, adding another chapter to their feud. In his second verse, he opens with bars about Christopher Reeve, a longtime target of Em’s vitriol. “First off, I did not even realize the guy died / so I guess them Christopher Reeves jokes ain’t gonna fly,” he raps, making fun of both Reeve’s paralysis and his time as the first live-action Superman. It’s a sharp dig that showed Em had not lost his sardonic sense of humor in his time off. Em delivers his verses in the accent he deployed on Relapse, one of his most divisive creative decisions to date. But as a piece of technical excellence, these are some of the strongest bars from the early part of Eminem’s comeback. Moreover, it served as a reminder of his capabilities as an MC.

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In 2013, Tim Westwood shared a freestyle between Eminem and Proof from 2000. It aired on his radio show back then, but Westwood left it publicly unavailable for over a decade. Leaving this in the vault for as long as he did was a massive disservice to hip-hop fans. It is two best friends working excellently together, with 10 minutes of bar after bar from the pair.

Em opens with a confident verse over Jay-Z’s “So Ghetto,” saying whatever comes to mind (“I clap hands with the rap fans, jump in their wheelchairs and give 'em a lap dance”). Proof follows him with Method Man-esque delivery that quickly reminds fans why Em called him the best freestyle rapper he’d ever seen. Eminem’s verses are from a man operating at the peak of his powers. His performance perfectly displays why fans hold his freestyle abilities in such high regard, but this is also the Proof showcase. 

In the years since Proof’s death, hip-hop hasn’t necessarily celebrated him in the way that he should be. However, Em holds him in such high regard as a rapper exactly because of what he did here (“Make you go-go like Gadget, perform magic without a wand, I drop bombs without Saddam / A vet' without 'Nam, I make sense without common ground,” is one of the gems Proof drops early in his second verse). 

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Fans and critics alike consider Eminem and Royce da 5’9’s appearance on the August 20, 1998 edition of Stretch & Bobbito to be one of the greatest radio freestyles of all time. For 12 minutes, the two of them sat down and rapped at the highest level, with multisyllabic and dense bars, head-spinning metaphors, and all kinds of pop culture references. It is a relentless display of everything hip-hop can be. It also ranks favorably among the strongest performances of either man’s careers, album cut, radio freestyle, or otherwise.

In total, there are nine full verses, each of which goes well over the “standard” 16 bars, between the two MCs. They don’t slow down for any of the (several) beat changes, and if anything, the switches motivate them to really test their limits as rappers. “A freak genius, too extreme for the weak and squeamish / Burn you alive till you screaming to be extinguished / 'Cause when I drop the science, motherf****rs tell me to stop the violence / start a fire and block the hydrants,” Em raps halfway through the last verse. It’s a verbal onslaught from the duo as soon as they start. Their competitive nature means that neither of them ever lets up. It’s an unquestionably excellent display from Bad Meets Evil, and one that confirmed Eminem would not be going anywhere.