3. The Trip (1967)

This film is like experiencing an acid trip without actually taking any LSD. The great Peter Fonda is left heartbroken after getting divorced from his cheating wife. He decides to drop a tab of acid to cheer himself up and goes on an all night adventure through seedy LA. During the trip, he encounters several people who try and help guide him, including Bruce Dern, Dennis Hopper, and Salli Sachse.

What really makes this film trippy is Roger Corman’s editing. The ‘Pope of Pop Cinema’ uses photographic effects and colorful lighting and includes several strange fantasy scenes, with one even featuring a little person riding a merry-go-round for no apparent reason. 

4. Brazil (1985)

Monty Python alumni Terry Gilliam is known for his weird and wonderful films, and Brazil is no exception. It’s a dystopian comedy about a bored bureaucrat who finds himself on the run from authorities while trying to find a woman from his dreams. Sounds strange right? Well, the visuals are just as head-scratching, with Gilliam shooting on a wide-angled lens and crafting some truly unique set designs. 

Brazil is another trippy epic that features a big-name cast, with Jonathan Price, Katherine Helmond, Robert De Niro, Bob Hoskins, and Ian Holm all starring. 

5. Inception (2010)

Inception seems to make just about every movie list written on this website. Arguably the crown in Christopher Nolan’s multi-layered filmography cap, it’s a real head turner.

Leonardo DiCaprio is an extractor, hired to dive into people’s dreams and draw out their deepest thoughts. He is hired to perform a three-layered dream that leads to all sorts of problems for his team. 

At times confusing, Inception is still relatively easy to follow. While it might not be as trippy visually, plot-wise it is an interesting idea from Nolan that he executes tremendously. The open-ended finale is also a nice touch.