This is one I'm gonna have quite a struggle with. Many years ago I saw an Ashy Larry mockumentary online (on either YouTube or Vimeo) that ran approximately 20-30 minutes, done partially as a faux-interview, which focused on his fictitious years after Chappelle's Show. In it, he became famous, left his girlfriend (leaving a note calling her an ashy motherfucker) and started dating white women and partying with only whites. Somewhere after that is an interrogation scene with 5 black women questioning his racial dating preferences, to which he responds (one of the few lines I remember near verbatim) "because a white woman never told me 'niggas ain't shit'". This is followed by him running back to his ex's apartment only to find her with a new man. The mockumentary ended with the interviewer questioning if he could compromise by going by Ashford Larry or Ashy Lawrence, and Ashy belligerently disagreeing.
I can't even find the title of this thing, and I've been looking for at least half a decade now. IMDB was not helpful, and I remember none of the actors besides Donnell Rawlings himself. Does anyone know what I'm talking about?