The Weird Semi-Fame of Hip Hop Personality Pain in Da Ass

Since Ray Liotta’s passing I have spent a lot of time Googling him and then happily traveling down various internet rabbit holes. 

When I looked up “Fuck you pay me”, one of his many iconic catchphrases from Goodfellas, Kanye West’s puzzling line in “Two Words” shows up but so do several other songs. 

The line in “Two Words”, incidentally, is “Two words, Chi-Town, raised me, crazy/So I live by two words, "Fuck you, pay me.”

Chicago similarly raised me crazy but despite also being a product of the Chicago public school system, I can’t help but note that “Fuck you, pay me” is four words separated by a comma. 

Liotta’s Goodfellas dialogue also popped up in another classic hip hop song, Jay-Z and DMX’s “Money, Cash, Hoes.” Around four minutes into the uncensored album version of the song Hop Hop personality Pain In Da Ass impersonates Ray Liotta in Goodfellas but with references to Jay-Z and Roc-A-Fella replacing references to organized crime. 

I did not remember that part, possibly because Hip Hop skits and spoken word shenanigans almost invariably beg to be fast-forwarded through. I was familiar with Pain in Da Ass, however, largely through his appearance on the seminal Notorious B.I.G and Jay-Z collaboration “Brooklyn’s Most Wanted.” 

“Brooklyn’s Most Wanted” famously featured two Rock and Roll Hall of Famers, giants and popular favorites for greatest rapper of all time. And some guy doing a Tony Montana impression that was loud and enthusiastic but not particularly accurate or good. 

And that’s crazy because Tony Montana is one of the easiest impressions to do because it’s just a cartoonishly hammy Cuban accent and collection of catchphrases. 

Yet here was some cornball doing hackneyed shtick on one of the greatest and most important Hip Hop songs of all time. 

How did he get on that song and a slew of other Roc-A-Fella tracks and skits as well? 

I did some online sleuthing and the answer did not surprise me. Once upon a time Pain in Da Ass, of the fabled Ass family, was just an unusually loud and obnoxious intern at Roc-A-Fella records with a penchant for impersonating actors from iconic gangster movies like Goodfellas, Carlito’s Way and Scarface. 

His shtick amused his bosses so he was invited to work his magic on a series of songs and skits from Roc-A-Fella artists, particularly Jay-Z. 

Here’s the thing about Pain in Da Ass. He wasn’t really a comedian. He also recorded a go-nowhere single entitled “OK, I’m Reloaded” that unfortunately established that he wasn’t really a rapper either. 

So what was Pain in Da Ass? He was a little guy with a big personality who was in the right place at the right time to make a contribution to some very important albums from important artists despite not possessing any real talent at all. 

He was something of a human novelty figure, like the dudes from The Mighty Mighty Bosstones and Black Monday who didn’t sing or play instruments but rather danced, and even that is being generous. 

Or he’s like Madd Rapper, the alter-ego of producer D-Dot and a persona so popular it got its own solo album with guests like Eminem, Kanye West and 50 Cent. 

Pain in Da Ass made a little go along way. As late as Jay-Z’s 2006 comeback album Kingdom Come Pain in Da Ass was still doing his thing because someone apparently still found it amusing. 

In some ways Pain in Da Ass wasn’t too different from another cocky kid hanging around the Roc-A-Fella offices, dreaming about getting their shot at the limelight and working all the angles: Kanye West. 

The difference is that Kanye had talent and Pain in Da Ass just had shtick. 

I checked out Pain in Da Ass’ Instagram account and it is exactly what you think it would be: a bunch of pictures of Roc-A-Fella luminaries and RIP posts about DMX and Ray Liotta. 

Pain in Da Ass doesn’t seem to have done much over the past decade or so but he still seems like the luckiest man in hip hop. He never attained the dizzying heights of his colleague Kanye West but in the grand scheme of things, that might be a good thing for him and his mental health if not his bank account. 

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