Long before Eminem became a global superstar, he was already earning respect in underground hip-hop circles—and one early appearance helped launch him into the spotlight.
The moment happened on The Wake Up Show, hosted by Sway Calloway and DJ King Tech. Wendy Day, founder of Rap Coalition, arranged for some of the top Rap Olympics competitors to appear on the show, including a young and hungry Eminem. For Em, it was the first time performing live on such a major platform—and he made the most of it.
In just a short freestyle, Eminem showcased the sharp wordplay and rapid-fire delivery that would soon become his trademark. Though the clip that circulates today is only about 30 seconds long, it’s more than enough to see the raw talent that caught people’s attention—even Dr. Dre’s.
By the time Jimmy Iovine passed Eminem’s demo tape to Dre, the legendary producer had already heard Em on the radio and was intrigued. That early Wake Up Show freestyle helped lay the groundwork for what would become one of the most iconic partnerships in hip-hop history.
The appearance also sparked a long-running friendship between Eminem and Sway. Not only did Marshall return for more freestyles over the years, but Sway would eventually become a regular presence on Eminem’s Shade45 radio station.
And for longtime fans, there’s a fun detail in the video: Eminem’s manager, Paul Rosenberg, is briefly seen on camera—sporting a hairstyle very different from what fans are used to today.
I had hair! https://t.co/ypelgs9k9f
— Paul Bunyan Rosenberg (@rosenberg) April 29, 2021
