10. Fear and Loathing in Las Vegas (1998)
For its sheer craziness and insight into the endless possibilities of a hallucinogenic-laced road trip, I couldn’t NOT include the adaptation of Hunter S. Thompson’s Fear and Loathing in Las Vegas. Directed by unique visionary Terry Gilliam and featuring oddball performances from Johnny Depp and Benicio del Toro, it tells the tale of an eccentric journalist and his attorney on a road trip to Las Vegas. We’re never entirely sure where they’ve come from or why they are going to where they are going, but it is not that which we are concerned with. It is one of the most unpredictable and directionless of films, reflecting an unsettling, unpredictable time and should not be ventured into by those looking for mild-entertainment or a simple A-to-B film. We cannot truly trust our two protagonists to get us to our destination safely, but we are supposed to just enjoy the journey and the wonderful visuals constantly being thrown our way. It is so stunning a film that we never once question what we have delved into…and by that point it’s too late to go back. What a trip!