OK this is entirely trivial, but I'm curious about the answers and a little levity on here may not hurt (nothing wrong with the more weighty threads either!!).

Have loved the Smile Orange movie for years and years and pull it out every 12 mo.s or so for some laughs.

Early in the film, when the new guests are arriving at the hotel, Joe (the cook) and Ringo (C Bradshaw's waiter) are observing the new assistant manager.
Ringo says of him (or I've always thought he says):

"him look like a black jackass looking over a whitewashed fence"

Given Ringo's low opinion of people in general, and the assistant mgr. in particular, I've always interpreted the line to mean something like he's trying to be something he is not.
However, I've never had a real explanation and any Jamaican I've asked is either too young to know the movie or doesn't provide much of an answer.

I've never found it anywhere else (even with all the search technologies).
Anyone heard it in any other context and/or have a deeper explanation?

check the quote in Google....there are a couple of links....I agree with your analogy....Black man acting like a "Uncle Tom"...trying to blend in being what you are not........

(no offense to anybody of any color, including white)

Rambo - thx for the reply - I have searched, but usually the closest return is "jumping over a w.w. fence" (as opposed to looking over) and appears to be related to a particular DJ. and/or detractor's remarks and I don't wish to add to their web-searches by adding/linking to it.

M. Yoder- thx as well, particularly if you actually phoned persons on behalf of my (IMO) foolish pursuit.
Side note to you - I really hope your upcoming trip is wonderful (and wish I was taking a similar trip instead - darn it).