[l-r: a literal 3rd generation rip-off of max fischer, dignan going through the motions, and beautiful sun dial-faced adrien brody doing his best to make his character more than "the one with the sunglasses."]
i could go off on this, and i mean OFF, like an entire separate website on the subject or a graduate thesis in cinema studies at some suspect university, but it basically breaks down like this: i love rushmore, love it like a man loves a woman (if that man isn't gay. and i guess if that woman isn't gay, either). all anderson output after that, not so much.
rushmore's chock full o'random quirk (mr. little jeans, hand jobs, budweiser swim trunks), but also cohesive quirk, little details that add up to themes that add up to lovely motifs. eg: when max first sees ms. cross, she's reading robinson crusoe, and we hear the sea. max's dad tells max he's like a clippership captain, married to the sea. then max tries to build ms. cross an aquarium. one of her students paints an octopus. then we find out that ms. cross' husband drowned. mr. blume has already done a high dive into his pool and let himself sink to the bottom. etc, etc.
that there are random slow motion moments, a supercool british invasion soundtrack, and meticulous visuals (sets, costumes, you name it) is a bonus, but they're not all that makes the movie great. there's real substance there beneath the artifice, genuine sincerity dolled up with hipster panache. it's stylish without being aloof. it's heartfelt without losing its sense of humor. it's a coming of age movie on par with harold and maude. it's just fuckin great.
and i would argue that every movie wes anderson has made since rushmore has been little more than rushmore afterbirth, because the use of quirk, music, and visuals are the same (sometimes exactly; the siblings in the royal tenenbaums basically add up to max, quirk-wise-- a better looking/more famous max fischer voltron, if you will). problem is, the heart is gone.
the characters have as much depth as the zombies song they die to in slow motion, and why wouldn't they, because nothing seems to be at stake. mr. blume explains his love for ms. cross by saying, "she's my rushmore, max," the thing he lives for, the center of his world. in these latter films, none of the characters seem to have their own rushmore. they just have mustaches, or headbands, or monogrammed belts, but those do not a compelling character/film make.
[margot tenenbaum wrote plays. max wrote plays. but he also did other things, things more substantial than wear eyeliner and enter dramatically to nico.]
so basically, the darjeeling limited is rushmore on its third trip through the washing machine. three sad brothers on a train with nothing much to do, so they say everything they're feeling about their dead dad while framed by stunning sets, fill time by walking slowly to the strains of a(nother) kinks song, and manage to have a short brush with bill murray. it's the ultimate in detached artifice, like a photoshoot for W magazine adapted for the screen. and-- symbolic spoiler alert-- when the boys finally come together at the end of their trip and run for another train, leaving their bags behind-- literally TOSSING THEIR BAGGAGE-- it's beyond shallow, it's lazy.
the darleeling limited (and the royal tenenbaums, and the life aquatic) is like max as we first meet him; too caught up in frivolities like calligraphy club and kite flying society to see what's really important, let alone risk what's really important and emerge victorious (to the vocal stylings of a young rod stewart). darjeeling has the calligraphy and the kites, but nothing of import, no risk, and no real victory. i can see max confronting these empty later characters-- "i saved latin! what did you ever do?" with no good answer for that, they'd probably just skulk away, ashamed. in slow motion. to a kinks song.