When I think of the most rewarding film-viewing experiences I’ve ever had, I have to give kudos to the confusing movies that I only properly understood upon a rewatch. While it’s great to have a film that can be immediately understood, sometimes actors, directors, and writers release more challenging works that must be revisited and reinterpreted through multiple screenings that add to our understanding of the overall narrative. This can be enjoyable as new details reveal themselves, and I pick up on narrative clues that went over my head the first time around.

I’ve found that some of the greatest directors who ever lived have also produced extremely confusing movies that must be rewatched to fully take in all the complex themes and ideas they presented. A director like David Lynch was known for his absurdist, dreamlike style, so I never gave myself a hard time if I needed to rewatch one of his movies before I fully understood it. Rewatching a film for the second time can often be better than the first viewing, as confusing movies become easier to understand in the context of the entire narrative.

8

The Big Sleep (1946)

Directed by Howard Hawks

The Big Sleep was among the best film noirs ever made and was also the very first film noir I ever watched. As a young film fan, I was excited to see this adaptation of Raymond Chander’s classic hardboiled detective story and immediately connected with the performances of Humphrey Bogart and Lauren Bacall. However, upon first viewing, I have to admit that once all the conspiracies had been uncovered and Detective Philip Marlowe had solved the case, I was incredibly confused and wasn’t fully sure I understood its convoluted resolution.

Having grown fond of film noirs, I learned this was the case with many 1940s detective stories and that, as a viewer, you’ve just got to go along for the ride. While there were plenty of twists and turns, a moody atmosphere, and a morally dubious femme fatale, the most enjoyable part of The Big Sleep was its style and how it presented its story. Upon rewatching, I enjoyed The Big Sleep without worrying about its confusing aspects and having seen it multiple times, I can comfortably say I mostly get it.

The Big Sleep - poster - Humphrey Bogart

The Big Sleep

Approved
Crime
Film Noir
Mystery

The Big Sleep is a 1946 film noir directed by Howard Hawks, featuring Humphrey Bogart as private detective Philip Marlowe. Based on Raymond Chandler’s novel, the film follows Marlowe as he investigates the blackmail of a wealthy family’s daughter, uncovering a web of crime and intrigue. Lauren Bacall co-stars as Vivian Rutledge, adding to the film’s electric atmosphere and complex narrative.

Director

Howard Hawks

Release Date

August 31, 1946

Writers

William Faulkner
, Leigh Brackett
, Jules Furthman
, Raymond Chandler

Cast

Humphrey Bogart
, Lauren Bacall
, John Ridgely
, Martha Vickers
, Dorothy Malone
, Peggy Knudsen
, Regis Toomey
, Charles Waldron

Runtime

114 Minutes

Main Genre

Film Noir

7

2001: A Space Odyssey (1968)

Directed by Stanley Kubrick

Dr Frank Poole wearing a yellow astronaut suit in 2001: A Space Odyssey (1968)

When I watched 2001: A Space Odyssey for the first time, it was clearly a masterpiece of cinema, but it also felt like I was missing something. From its epic prehistoric introduction to the elusive alien monolith, I understood this was a film rife with meaning and symbolism. However, unlike other Stanley Kubrick films that I felt I got right away, such as The Shining and Full Metal Jacket, 2001: A Space Odyssey left me scratching my head as the credits rolled.

Despite its confusing nature, I returned to 2001: A Space Odyssey and connected with its themes of mankind’s origins and the universe’s destiny. While the meaning of the monolith was lost on me the first time around, when rewatching, I felt it connected the disparate aspects of the film and gave it a cohesive message about our evolution from ape-like primates into space-traveling explorers. I can’t say I understand every minute detail of 2001: A Space Odyssey, but every time I watch, it reveals new dimensions of itself to me.

2001: A Space Odyssey

G
Adventure
Mystery
Sci-Fi

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2001: A Space Odyssey is one of Stanley Kubrick’s most well-known films. A science-fiction epic, the film tells the story of the journey of Discovery One, a spacecraft operated by a group of scientists, astronauts, and a sentient computer, on a mission to Jupiter to investigate a mysterious monolith. Considered one of the greatest films ever made, Kubrick combines sparse dialogue with the heavy use of scoring and ambiguous imagery to create something that eschews conventional filmmaking. 

Director

Stanley Kubrick

Release Date

April 2, 1968

Studio(s)

Metro-Goldwyn-Mayer

Distributor(s)

Metro-Goldwyn-Mayer

Writers

Stanley Kubrick
, Arthur C. Clarke

Cast

Keir Dullea
, Gary Lockwood
, William Sylvester
, Daniel Richter
, Leonard Rossiter
, Margaret Tyzack

Runtime

149 minutes

Budget

$12 million

6

Mulholland Drive (2001)

Directed by David Lynch

Naomi Watts and Laura Harring in Mulholland Drive

The work of director and visionary David Lynch has always been best interpreted individually, rather than trying to place some definitive meaning on it. As a filmmaker who has always connected with the more absurd and dreamlike aspects of existence, the confusing nature of Lynch’s films extended into Mulholland Drive. This powerful psychological thriller is best described as an inscrutable mystery box, and I did not get it the first time around.

Mulholland Drive was so confusing upon first viewing because it originated as a television pilot and was filmed in a way that kept the story open-ended for a potential series. With a dreamlike feeling that brought to mind themes of celebrity, Hollywood, and falsities, watching Mulholland Drive for the second time was a much more enjoyable experience because I knew what to expect. With the knowledge that it would never come together as a cohesive whole, I could accept the film on its own terms and make my own meaning from Lynch’s cryptic vision.

Mulholland Drive

R
Mystery
Thriller
Drama

Where to Watch

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David Lynch’s Mulholland Drive is a neo-noir mystery about aspiring actress Betty, who becomes involved with a woman suffering from amnesia and a mysterious blue box. Starring Naomi Watts and Laura Harring, the 2001 surrealist film explores themes of identity, memory, and Hollywood’s dark side.

Director

David Lynch

Release Date

October 19, 2001

Studio(s)

Universal Pictures

Distributor(s)

Universal Pictures

Writers

David Lynch

Cast

Laura Elena Harring
, Mark Pellegrino
, Justin Theroux
, Naomi Watts
, Ann Miller

Runtime

147 minutes

Budget

$15 million

Betty in Mulholland Drive

Related

David Lynch’s DVD Clues To “Unlocking” Mulholland Drive

For David Lynch’s Mulholland Drive DVD release, the famously tight-lipped director added 10 clues for viewers to use to unlock the story.

5

Primer (2004)

Directed by Shane Carruth

Primer 2004 Wallpaper

The cult sci-fi movie Primer presented time travel in a way I had never previously encountered in a feature film. I believe describing Primer as merely confusing would be a disservice, as its script was so dense and complex that it truly boggled the mind upon first viewing. Written, directed, produced, and starring Shane Carruth, Primer was truly a singular vision that did not dumb itself down to appeal to the average viewer and required multiple rewatches to really get the hang of what exactly it all meant.

Primer was made on a shoestring budget of just $7,000 and took in an impressive $841,926 (via The Numbers) at the box office. I imagine a lot of its earnings came from viewers returning to the theaters for a second chance to understand everything that went on. Primer was confusing, and I won’t get into the specifics of trying to break it down beat by beat. But those willing to put in the time and return for repeated viewings will be rewarded with a highly enjoyable and satisfying time-travel movie.

Primer Movie Poster

Primer (2004)
PG-13
Drama
Sci-Fi
Thriller

Four friends/fledgling entrepreneurs, knowing that there’s something bigger and more innovative than the different error-checking devices they’ve built, wrestle over their new invention.

Director

Shane Carruth

Release Date

October 8, 2004

Studio(s)

Studio Canal

Distributor(s)

THINKFilm
, IFC Films

Writers

Shane Carruth

Cast

Shane Carruth
, David Sullivan
, Casey Gooden
, Anand Upadhyaya
, Carrie Crawford
, Samantha Thomson
, Brandon Blagg

Runtime

77 Minutes

Budget

$7,000

Main Genre

Sci-Fi

4

Eternal Sunshine of the Spotless Mind (2004)

Directed by Michel Gondry

Kate Winslet and Jim Carrey in Eternal Sunshine Of The Spotless Mind

Eternal Sunshine of the Spotless Mind was an extraordinary sci-fi romance that told the story of Joel Barish (Jim Carrey) having the memory of his old girlfriend Clementine Kruczynski (Kate Winslet) erased from his mind. While the major plot points were not difficult to understand, the non-linear nature of Eternal Sunshine of the Spotless Mind meant I did not notice the nuances of its story until the second viewing. While I enjoyed it the first time around, it was upon rewatching that it became one of my all-time favorite films.

Jim Carrey gave one of his very best performances as Joel and I connected with the heartfelt vulnerability of the story in Eternal Sunshine. Only after watching it twice did I realize Joel and Clementine were meeting again after having already erased their previous relationship. The cyclical nature of Eternal Sunshine presented a powerful message about the need to work through our feelings naturally and that even though breaking up hurts, it’s necessary to feel that pain and hold onto our memories of past love.

Eternal Sunshine of the Spotless Mind

R
Romance
Sci-Fi
Drama

Where to Watch

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Jim Carrey and Kate Winslet star in Eternal Sunshine of the Spotless Mind as Joel Barish and Clementine Kruczynski, a couple who rediscover their love after erasing each other from their memories. The 2004 drama is written by Charlie Kaufman, directed by Michel Gondry, and includes Mark Ruffalo, Elijah Wood, Kirsten Dunst, and Tom Wilkinson in its cast.

Director

Michel Gondry

Release Date

March 19, 2004

Studio(s)

Universal Pictures

Distributor(s)

Focus Features
, Universal Pictures

Writers

Charlie Kaufman

Cast

Kate Winslet
, Jim Carrey
, Elijah Wood
, Kirsten Dunst
, Mark Ruffalo

Runtime

108 minutes

Budget

$20 million

3

I’m Not There (2007)

Directed by Todd Haynes

Cate Blanchett in I'm Not There

The first time I watched Todd Hayne’s unusual Bob Dylan biopic, I’m Not There, I was a casual fan of the iconic folk singer but did not have in-depth knowledge of his life story and history. I quickly realized this was a mistake, as I’m Not There was not a typical biopic, and instead, six different actors were cast to play the many facets of Dylan’s public persona. While I enjoyed Cate Blanchett’s portrayal of Dylan in his classic mid-1960s era, Christian Bale playing a born-again Christian completely went over my head.

I returned to I’m Not There years later and found upon a rewatch that what had previously confused me was now rife with meaning as I understood more about Dylan’s life story. I could appreciate how Marcus Carl Franklin, playing an 11-year-old African American boy named Woody Guthrie, was linked to Dylan’s earliest influences in folk music. When rewatching for the second time, I realized that Richard Gere’s role as Billy the Kid was intrinsically linked to Dylan’s real-life movie role in the film Pat Garrett and Billy the Kid.

Im Not There Film Poster

I’m Not There
R
Biography
Drama

Where to Watch

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An innovative biographical film that reimagines the life of Bob Dylan through six distinct characters, each symbolizing a different phase of his career and personality. Portrayed by a diverse cast including Christian Bale, Cate Blanchett, and Heath Ledger, these characters navigate through the various transformations of Dylan’s life—from his early days as a folk singer to his electric phase and beyond.

Director

Todd Haynes

Release Date

October 1, 2007

Writers

Todd Haynes
, Oren Moverman

Cast

Cate Blanchett
, Ben Whishaw
, Christian Bale
, Richard Gere
, Marcus Carl Franklin
, Heath Ledger

Runtime

135 minutes

Main Genre

Biography

2

Synecdoche, New York (2008)

Directed by Charlie Kaufman

Synecdoche, New York 2008

When watching Charlie Kaufman’s postmodern drama Synecdoche, New York, I was first struck by its grand scope. With Philip Seymour Hoffman as an ailing theater director staging an elaborate production where the lines between reality and performance blurred, I was focused on just taking it all in during my first viewing. As the story progressed over decades, Caden Cotard’s play became increasingly complex. I have to admit, at times, I got lost amid the dense script, insightful symbolism, and careful attention to detail in Synecdoche, New York.

After the credits of Synecdoche, New York rolled, I knew I had seen a special film, but I also knew I wanted to watch it again with knowledge of the full story. The second viewing became an even more enriching experience, as details about Caden’s life and those around him that had previously gone over my head were as clear as day. I think Synecdoche, New York was Charlie Kaufman’s greatest film and the summation of all the themes he has previously explored in works like Being John Malkovich and Adaptation.

Synecdoche, New York (2008)

Synecdoche, New York
R
Drama
Documentary

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A theatre director struggles with his work, and the women in his life, as he creates a life-size replica of New York City inside a warehouse as part of his new play.

Director

Charlie Kaufman

Release Date

October 24, 2008

Writers

Charlie Kaufman

Cast

Philip Seymour Hoffman
, Catherine Keener
, Sadie Goldstein
, Tom Noonan
, Peter Friedman
, Charles Techman

Runtime

124 minutes

Main Genre

Drama

1

The Lobster (2015)

Directed by Yorgos Lanthimos

Colin Farrell and Rachel Weisz running through high grass in The Lobster

Yorgos Lanthimos is one of the most interesting and unique directors working today. Still, I have to admit that his unconventional style and darkly comic narratives can often take multiple viewings to hit home. The Lobster was one of these movies, as although I could appreciate the satirical black comedy at the heart of its concept, its deadpan narrative was alienating when seen for the first time. I was impressed by Colin Farrell’s reserved performance, but the true genius of The Lobster was not immediately apparent to me.

However, when watching The Lobster for the second time, I was struck by how effectively the film deconstructed societal expectations around love and romance. When rewatching The Lobster, I noticed many hidden details, such as the various animals that unsuccessful singletons had been turned into looming in the background. The Lobster was an eccentric and substantial film with much more to offer than was initially obvious when experienced for the first time.

The Lobster (2015) - Poster - Collin Farrell

The Lobster (2015)

R
Comedy
Drama
Romance

The Lobster is a dystopian romantic comedy set in a world where single people are forced to find a mate within 45 days or be turned into an animal. The film follows David, a recently divorced man, who checks into a hotel where he has 45 days to find a new partner, or else he will be transformed into a lobster.

Director

Yorgos Lanthimos

Release Date

October 15, 2015

Studio(s)

Scarlet Films
, Haut et Court
, Eurimages
, Lemming Film
, Element Pictures
, Nederlands Fonds voor de Film
, Greek Film Centre
, Faliro House Productions
, Limp
, Film4 Productions
, Protagonist Pictures

Writers

Yorgos Lanthimos
, Efthymis Filippou

Cast

Colin Farrell
, Rachel Weisz
, Olivia Colman
, Lea Seydoux
, Michael Smiley

Runtime

119 Minutes

Budget

4000000.0

Main Genre

Comedy

Source: The Numbers