No. 41: Fat Joe

For some reason, my tremendously massive bias against fat people doesn't really apply to rappers.

I had plenty of love for Chubb Rock and the late Heavy D, both of whom narrowly missed the cut for this countdown, and I forgave the ferociously talented Big Pun for pilfering a hook from me back in the day (for a cut on the Tony Touch mixtape...it's almost impossible to write it off as coincidence).

And I've got room in here for the man who brought Pun out — Joseph "Fat Joe" Cartagena — despite a blatant period of sell-the-fuck-outism a decade or so ago.

Joe released his first solo LP, Represent, in 1993, and immediately earned a place as one of the most respected emcees in hip hop. After a solid second album, Jealous Ones Envy, he made an appearance on one of the last relevant LL Cool J tracks ever, 1995's "I Shot Ya" remix.

Ahh yeah...you brought that cheeseburger, right?

Around that same time, Joe dropped a "freestyle" (why they try calling them that I'll never understand) for the first Funkmaster Flex album alongside his protégé Big Punisher, and it could almost be viewed as a mistake in terms of how it shaped Fat Joe's legacy. As respected as he had been, he inadvertently gave away his spot as the best Latino rapper on the planet to his more talented friend. The two collaborated multiple times, most notably on Pun's "Deep Cover" remake, "Twinz," and as dope as Joe was you couldn't help but think about how much he was being overshadowed by the monster he created.

Even being outdone by Pun, though, Fat Joe could probably have ranked at least 10 spots higher on this list had he not made the mistake of releasing Jealous Ones Still Envy in 2001. Produced by the loathsomely wack Irv Gotti, the album was chock full of radio-friendly songs featuring the likes of R. Kelly, Ashanti and the joke formerly known as Ja Rule. It was a blatant attempt to sell out, and in terms of respect, it was damn near a career-killer.

True hip-hop heads usually rebound, though, and Joe managed to win back a few of his real fans with the banger "Lean Back" (a track recorded with his underlings Terror Squad) in 2004. He's kept busy since, seemingly going back and forth between attempts to sell records (cuts with Lil' Wayne) and make quality hip-hop tracks (such as the DJ Premier-produced "That White").

As with some others on this list, Fat Joe's money-grab disappointments keep him lower on this list than he could have been, but when he wants to be good, his talent is undeniable. It's enough to get him here.