Jay-Z's most famed pre-Reasonable Doubt apperance isn't a song, but this February 23, 1995 freestyle session with the late Big L from Stretch Armstrong and Bobbito's Thursday-night radio show on New York's WKCR. The consensus years later is that Hov met his match that night, in a Big L already at the top of his game (L's debut Lifestylez ov Da Poor and Dangerous was already in the bag at this time).
Granted, Jay's verses have some misses that would probably make him cringe today—even harder than he does in those Samsung commercials. (Seriously, what was up with that "Bitta Boo Boo Boo Bam" stuttering baby talk thing he does in his second verse?) But he definitely shows flashes of the brilliance to come ("I'm too cocky, to stop me you gotta kill me/And when I'm gone you can still feel me") on what has come to be known over the years as simply "The 7 Minute Freestyle." The recording (over Milkbone's "Keep it Real" instrumental) is so legendary we named it No. 1 on our list of the 50 Best Radio Freestyles.