Recognizing the futility of this debate, this clip is still a pretty sick example of both their freestyle skills. As for the winner, hard to say. Personally, I've always had a partiality towards the Notorious one, much more so than Tupac, whom I like but don't love.

I want to say Biggie takes it. He comes in blazing, with the clever enumeration of his arsenal "I've got seven Mack 11's, about eight .38's,  nine 9's, ten Mack 10's, the shit never ends...." His freestyle continues to impress, showcasing Biggie's incredible voice control, like the way he speeds or slows down his raps for effect, e.g., "Everybody hit the D-E-C-K." And we get the trademark dirty humor in lines like "I give MC's the runs drippin'" or "Oh my god I'm droppin's shit like a Pigeon!"

Based on the lyrical content and delivery, I really want to hand the trophy over to the Brooklyn Lochness. But I'm hesitant.

Although I'm far from his biggest fan, I recognize Tupac's gifts lay beyond deft wordplay or vocal control, though he sometimes concocts excellent lyrics. What Tupac does better than any other rapper is deliver raw emotion. BIG makes you stop for a second to regard how clever or compelling his lyrics are; Tupac embodies the emotional content of his songs. You end up feeling it, and often sort of forgetting the words.

And while Biggie impresses with the scope of his allusions ("little Gotti got the shotty to your body"), Tupac usually plays it a little closer to the street, evidenced in his claim to have been born "bucking at the bustaz", a reference to Blood-Crip violence- though not one casual rap fans would likely recognize.

A few lines in particular restrain my impulse to immediately call the battle in BIG's favor. Their emotional message, in my interpretation, is a celebration of unbridled power, freedom, and ego to the point of ecstatic recklessness:

"You see me strikin down the block, hittin corners
Mobbin like a motherfucker, livin like I - wanna
And aint no stoppin at the red lights, Im sideways
Thug life motherfucker crime, pays!"

Hard!

Lyrics transcribed below for your thoughtful analysis (and enjoyment):

[notorious b.i.g.]
One two, one two, gonna do it like this
Where brooklyn at, where brooklyn at
Where brooklyn at, where brooklyn at
We gonna do it like this
Anytime youre ready, check it

I got seven mack 11s, about eight 38s
Nine 9s, ten mack tens, the shits never ends
You cant touch my riches
Even if you had mc hammer and them 357 bitches
Biggie smalls; the millionare, the mansion, the yacht
The two weed spots, the two hot glocks
Thats how I got the weed spot
I shot dread in the head, took the bread and the lamb spread
Little gotti got the shotty to your body
So dont resist, or you might miss christmas
I tote guns, I make number runs
I give mcs the runs drippin
When I throw my clip in the ak, I slay from far away
Everybody hit the d-e-c-k
My slow flows remarkable, peace to matteo
Now we smoke weed like tony montana sniffed the llello
Thats crazy blunts, mad ls
My voice excels from the avenue to jail cells
Oh my god, Im droppin shit like a pigeon
I hope youre listenin, smackin babies at they christening

[tupac] motherfuckin biggie smalls!
[kane] what you gonna do with it tupac?

[tupac]
Yeah where the motherfuckin thugs at?
Throw your motherfuckin middle finger
We gonna do this shit like this
I thank the lord for my many blessings, never stressin
Keep a vest for protection, from the barrel of a smith & wesson
And all my niggaz in the pen, here we go again
Aint nuttin separatin us from a mack-10
Born in the ghetto as a hustler, told ya
A straight soldier, buckin at the bustaz
No matter how you try, niggaz never die
We just retaliate with hate, then we multiply
You see me strikin down the block, hittin corners
Mobbin like a motherfucker, livin like I - wanna
And aint no stoppin at the red lights, Im sideways
Thug life motherfucker crime, pays!
Let the cops put they lights on, chase me nigga
Zig zaggin through the freeway, race me nigga
In a high speed chase with the law
The realest motherfucker that you ever saw