Top 10 Awkward Wes Anderson Movie Moments

With the heavily-anticipated release of Moonrise Kingdom from writer/director Wes Anderson, I realized from speaking with many, that most moviegoers either adore or hate the man. Staying positive, I decided to seek out what led people to love him and ended up coming up with quite the list. My personal favorite trait of Wes Anderson’s films is the awkward moments.

Whether it be an awkward relationship proposal or a son seeking approval from his father, the moments are relatable and tastefully clumsy. These key Wes Anderson moments are amusing and compelling, and if you’re a fan of them, believe me, Moonrise Kingdom will not let you down. Here are the Top 10 Awkward Wes Anderson Movie Moments. As always, email eric@scene-stealers.com if you’d like to contribute a Top 10.

10. Bank robbery from Bottle Rocket (1996)

Without a doubt, the awkward moments in Bottle Rocket are the most subtle. It’s because of this that the film does not appear much on this list. Moment 10 finds both Anthony (Luke Wilson) and Dignan (Owen Wilson) in the middle of their first legitimate robbery. The two men are clearly nervous and excited about the act, but unsure of how to go about it. The macho man exterior that Dignan puts on is unfitting and contrived and because of this, the library staff see right though it. In moment 10, Dignan is shouting at the library manager to put money in tiny paper bags and calls him an idiot. This is the last straw for the manager and he snaps at Dignan. From then on in the robbery, Dignan addresses him respectfully saying, “sir”, and “thank you.”

9. Back from lunch in Bottle Rocket (1996)

Moment nine is a follow-up to moment 10 and seems to present a theme. In their big moment of glory, Dignan, Anthony, and their weaker sidekick Bob (Robert Musgrave) crumble under pressure and leave their posts, only to end up arguing with each other. This action proves to be fatal when the band misses that the employees of the plant they are robbing return from lunch to find men in yellow jumpsuits scrambling inside for cover. Had the main trio stuck to the plan, they would have most likely made a clean escape, but their truly weak backbones show clearly, and all does not end well.

8. Confidence booster from Fantastic Mr. Fox (2009)

Moment number eight is led full force by the stop-motion marvel Fantastic Mr. Fox. Ash (Jason Schwartzman), is the son of Mr. Fox. Ash has a slight inferiority complex, stemming from his admiration of his father’s near non-acknowledgment and his desire for acceptance. When Ash’s cousin Kristofferson (Eric Chase Anderson) comes to town and completely destroys the little amount of self-confidence Ash has, he begins to question most anyone about how great he is. This specific moment takes place at school when the gym class is playing something called “whack ball.” Ash asks Coach Skip (Owen Wilson) if he believes he will ever be as good as his father (former whack ball champion) to which Coach Skip gently responds, “You don’t want to have to compare yourself to that.”

7. “Gay earring” from The Life Aquatic with Steve Zissou (2004)

The drive for acceptance is a common theme of Wes Anderson’s awkward moments. The Life Aquatic is no exception to this. This film seems to illustrate this theme the most. Whether it be physical appearance or emotional appearance, Anderson’s characters always seem to have some sort of lack of confidence eating away at them. This leads the characters to seek acceptance like hungry birds. As Ned (Owen Wilson) is getting to know his suspected father, Steve Zissou (Bill Murray) the two overhear the conversation at a table close by and realize that the group is talking trash on Steve Zissou. One member of the group specifically mentions the “gay earring” Steve has recently started wearing. This causes Steve to have a slight emotional meltdown based on the current washed-up appearance of his public image. They leave the restaurant and outside Steve throws his earring away, only to have Ned retrieve it.

6. Guilt is good from The Darjeeling Limited (2007)

The struggle for acceptance is treated somewhat differently in The Darjeeling Limited. Francis (Owen Wilson) sits his two brothers (Jason Schwartzman and Adrien Brody) down to lunch on the train he has just convinced them to travel with him on. He tells them the story of why his face is wrapped in bandages and uses the story to guilt them into accepting all of his crazy plans for the trip. Many times, the awkward Wes Anderson moment is a character trait or a punchline (in its own weird way), but here it’s the basis for the entire plot of the film. Francis gets what he wants and they continue on with their journey.

5. Dinner with teacher from Rushmore (1998)

Moment number 5 includes the line, “I wrote a hit play!” To accompany awkward dinner table moments, we have the well-known scene from Anderson’s Rushmore in which Max (Jason Schwartzman) is extremely upset that his crush (and teacher), Rosemary (Olivia Williams), has brought a date (Luke “These are OR scrubs” Wilson) to his after-play celebration dinner. Max gets drunk and ends up making his feelings all too obvious for comfort, finally crystallizing with “I wrote a hit play!”

4. Margo’s secrets from The Royal Tenenbaums (2001)

Moment four is centered entirely on Margo Tenenbaum (Gwyneth Paltrow). After Richie (Luke Wilson) attempts suicide, we find the family sitting silently in the recovery room. Raleigh St. Clair (Bill Murray) uses this moment to call out Margot on her string of lies and deceit. The two do not look directly at each other the entire time and this only adds to the distance between them. Margot’s family sits across from them out of frame, and her mother asks what she’s talking about. It is in this moment that all of Margot’s secrets are brought to light. The Margot everyone knows is now somewhat of a stranger and her false acceptance is now gone. Again, not too funny, but a big moment in the movie.

3. Feather ritual from The Darjeeling Limited (2007)

Awkward moment number three comes with the three brothers in The Darjeeling Limited. After being kicked off the train, they are at rock bottom. Having not gotten along very well through their trip, the three seem to be speaking nonsense to each other. Francis (Wilson), being the ringleader that he is, persuades his two brothers to do a ritual involving feathers in the desert to draw them closer together. With nothing better to do, the three set out to complete this task, only to return and find that they’ve all done the ritual incorrectly. It is at this point that we see the breakdown of communication within the family that has caused them to get to the point they are.

2. Sympathy from teacher in Rushmore (1998)

The second most awkward moment of all Wes Anderson films is one of his early ones. Throughout the movie Rushmore, Max attempts to woo Rosemary into submission to his advances. Rosemary repeatedly shuts him down and Max always seems to come back for more. At the point we think Max has finally given up, Max suddenly emerges through the window of Rosemary’s house. Getting too close to Max’s face in order to clean what appears to be a large wound on his forehead results in a large passionate kiss. It is only them that Rosemary discovers that the wound is fake and this has only been another of Max’s schemes. (If anyone finds the image from this actual moment, please leave a comment below!)

1. “Stevzie” from The Life Aquatic with Steve Zissou (2004)

It was hard naming the most awkward moment of Wes Anderson’s films up to this point, but I feel very confident that the number one, absolute, most awkward moment is from The Life Aquatic. Bringing back Anderson’s theme of father-son acceptance, we see Ned and the rest of the Zissou crew diving to a mysterious signal that has been showing up on their scanners for a days. Ned suddenly asks Steve if he can please call him Dad, a request Steve awkwardly rejects. What makes this moment awkward is not only the exchange between Ned and Steve, but the fact that there are multiple crew members in the water on the same radio feed, participating in the same conversation. It is settled that Stevzie is an acceptable name, and the crew swims off only to leave Ned behind contemplating what has just happened.

Adam Brumback

Recent college grad Adam Brumback spends most of his time with his girlfriend and four cats. Adam is also invested in the local music scene; playing drums in Regret, the Informer and providing media content for The Record Machine. You can view his personal work here.