After his directorial debut Bottle Rocket was a hit with film industry insiders but a bomb at the box office, Wes Anderson finally broke through with his sophomore effort, Rushmore, a coming-of-age comedy about an eccentric 15-year-old who falls in love with one of his teachers. Jason Schwartzman made an icon out of the lead character, Max Fischer, who’s arguably an even weirder teen than Napoleon Dynamite.

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Schwartzman is surrounded by great supporting actors, from Bill Murray to Olivia Williams to Brian Cox, and they all delivered the hysterical lines in Anderson’s screenplay (co-written with Owen Wilson) with pitch-perfect timing.

“My Safety’s Harvard.” – Max

Max sitting on a go kart in Rushmore

Max is so confident in his academic abilities that he not only thinks he can get into Harvard, it’s his safety option. He says, “My top schools where I want to apply to are Oxford and the Sorbonne. But my safety’s Harvard.”

The movie reveals that Max is, in fact, a terrible student. He’s smart and he’s heavily involved in extracurricular activities, but his actual studies are going poorly.

“Take Dead Aim On The Rich Boys.” – Blume

Bill Murray hiding behind a tree in Rushmore

Herman Blume’s opening speech to the Rushmore Academy students is hysterically inappropriate, and Bill Murray’s deadpan delivery really sells it.

He goes on a tirade about the privileged rich kids: “Some of you... were born rich and you’re going to stay rich. But here’s my advice to the rest of you: take dead aim on the rich boys. Get them in the crosshairs and take them down. Just remember, they can buy anything, but they can’t buy backbone. Don’t let them forget it. Thank you.”

“With Friends Like You, Who Needs Friends?” – Dirk

Dirk Calloway dressed as a wizard in Rushmore

Dirk Calloway is Max’s younger sidekick whom he tutors. Dirk feels betrayed by Max when he spreads lies about Dirk’s mother to increase his own street cred.

Max insists that he’s Dirk’s friend, but Dirk has a few powerful words to make him think about his actions: “With friends like you, who needs friends?”

“I’ll Just Go Back Out The Window.” – Max

Jason Schwartzman as Max Fischer reading a book in Rushmore

In a desperate bid to win over Miss Cross, Max comes to her bedroom window with his head bloodied, claiming to have been hit by a car. She invites him in and does some first aid before realizing it’s fake blood.

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When it becomes apparent that his romantic gesture has failed and Max goes to leave, Miss Cross says, “I’ll show you the door,” and Max says, “I’ll just go back out the window.”

“She’s My Rushmore, Max.” – Blume

Bill Murray standing outside Rushmore Academy in Rushmore

Ultimately, what reconciles Max and Blume’s friendship is getting their heart broken by the same woman. Early in the movie, Blume asks Max for “the secret” and Max tells him, “I guess you’ve just gotta find something you love to do and then do it for the rest of your life. For me, it’s going to Rushmore.”

Later, Blume tries to explain how much Miss Cross means to him and says, “She’s my Rushmore, Max.” Max simply replies, “I know. She was mine, too.”

“Don’t Get Nasty, Brother.” – Magnus

Stephen McCole as Magnus Buchan in Rushmore

Stephen McCole appears in Rushmore as Max’s Scottish classmate Magnus Buchan. The two often butt heads and Max takes it a step too far when he says, “Your mind’s as warped as your ear, Magnus.”

Magnus sternly says, “Don’t get nasty, brother.” Max later makes it up to Magnus by giving him a role in his ambitious, sprawling play set during the Vietnam War.

“112 Pounds. Black Hair. Glasses. Oval Face.” – Blume

Max is arrested at school in Rushmore

When Blume is driving into the school parking lot to pick up his kids, he tries to apply the brakes and they don’t work. The car spins out of control, narrowly avoiding oncoming traffic, and rolls to a stop in the quad.

As he gets out of the car and inspects the damage, Blume immediately knows who’s responsible. He describes Max to the police over the phone: “112 pounds. Black hair. Glasses... Oval face.”

“I Saved Latin! What Did You Ever Do?” – Max

Max Fischer writing on the blackboard in Rushmore

The main conflict in Rushmore is the love triangle between Max, his teacher Miss Cross (who makes it very explicit from the beginning that she’s not interested in him), and Max’s wealthy industrialist friend Herman Blume.

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When Blume confesses to Max that he’s in love with Miss Cross, Max feels betrayed because he was in love with her first. Max angrily compares himself to Blume: “I saved Latin! What did you ever do?”

“Kids Don’t Like It When Their Parents Get Divorced.” – Blume

Bill Murray as wealthy industrialist Herman Blume in Rushmore

Throughout Rushmore, Herman Blume is going through a divorce. When he sees his wife with her new boyfriend, he jumps in the pool and sits at the bottom for a while, à la The Graduate. During the bitter legal proceedings, his kids start acting out.

He has a beautifully blunt but apt explanation for their erratic behavior: “Kids don’t like it when their parents get divorced.”

“Oh, Are They?” – Max

The dinner scene in Rushmore

When Max invites Blume and Miss Cross to dinner after the premiere of his “hit play,” Miss Cross brings a date — Dr. Peter Flynn, a much more age-appropriate suitor — and Max is distraught.

He spends the evening knocking back wine and trying to upstage Peter. He says, “I like your nurse’s uniform, guy,” and Peter says, “These are O.R. scrubs.” Max hilariously quips, “Oh, are they?”

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