Rum Diary (2011)
If you're looking for the craziness of later Hunter S. Thompson, you'll find shreds of it here. In a way this is a more cogent movie than say "Fear and Loathing " but it's also a bit prosaic beneath the wilder stuff that peppers the surface. Johnny Depp stars and runs the show in his usual strong if uninspired way as a new, hard-drinking reporter with a failing English language newspaper in Puerto Rico.
There is a true surface here that's pretty amazing--the cars, the low down rot of the apartments, the racism between the rich white Americans and the indigenous Puerto Ricans. The depth you might expect and want here is slim, however, even though all the pieces are in play for a great drama--a charming troubled writer in a land filled with prejudice and violence and great natural beauty. It pushes the clichés too hard, and it's generally agreed (even by Thompson) that the material is weak and "rambling." The movie doesn't rearrange it enough to make it work.
You can in a way watch this for those surfaces, if you don't need too much more. There are several secondary characters who do their best to be a bit insane, including Giovanni Ribisi as a drugged out waif of a reporter, something like what Thompson himself might have become later in life. (See of course the Depp in the imperfect 1998 "Fear and Loathing in Las Vegas" for a sense of the famous freewheeling selfish addled sometimes brilliant Thompson.)
The director here also adapted Thompson's book and if he gets the credit for the nice ambiance of the film he also gets the burden of how clunky, choppy, and sometimes slow it is, even with such exciting material. It's not a horror, it's watchable, but you'll flag here and there. Even the end, without giving a thing away, is a bit deflating.