You probably remember the first time you saw Iron Solomon in a rap battle. Whether it was live on the streets or online, there’s no question you were instantly captivated. Sure, he’s a white guy with glasses who can rap his ass off, but that’s not the only draw. With Iron Solomon, it’s deeper than rap, and larger than race. He has the ability to break down any opponent, on the spot, all the time, with no fear.

Iron Solomon, who grew up in Manhattan on the Upper West Side aka South Harlem (shout to ItsTheReal), started on the battle scene in his late teens by hitting up well known Manhattan-based open mics and competitions like Braggin’ Rights and End of the Weak, making a name for himself as a skilled lyricist with a knack for humorous couplets and witty punchlines.

After taking out underground legend Immortal Technique in his late teens, Iron Solomon got the taste for blood, and went on to verse anyone and everyone who presented a challenge, eventually dethroning the Asian assassin Jin at New York’s premiere battleground Fight Klub with thousands of dollars on the line.

From there, Solomon was in high demand for big-time rap battles. He made an unforgettable appearance on Smack DVD at Fat Beats in New York against the roughest, toughest battler on the scene, Math Hoffa (who had literally knocked out his previous opponent with a fist to the face). He jaw jousted with 106 & Park champion Avalanche in Detroit. He went toe to toe in Miami with Philly street sweeper (and MTV’s Making The Band alumnus) E. Ness, all of which garnered hundreds of thousands of video views (his battle with E. Ness currently clocks in at 1.3 million clicks). Thanks to YouTube, we can all enjoy his various roastings endlessly.

Iron Solomon has been planning to step away from the battle scene to focus on recording for some time. Now he’s gearing up to release his debut album Monster on March 27th through Royal (Iron's imprint) and a partnership with 3D (a subsidiary of Duck Down).

As he makes his transition from the streets to the studio, we asked him to tell the tales behind his Top 5 Battles Of All Time. From the set-up, to the comeback, to the final punchline, it’s all here.

As told to Dan Isenberg (@StanIpcus)