50. Jane Winslett-Richardson (Cate Blanchett in “The Life Aquatic With Steve Zissou”)
Perhaps a little underwritten for an actress of this caliber (it’s a shame that she’s not yet had a second trip to Wes World), heavily pregnant journalist Winslett-Richardson, caught in a love triangle between Zissou and Owen Wilson’s Ned, still lets Blanchett mine a rich vein of pre-parental neurosis.
49. Henry Sherman (Danny Glover in “The Royal Tenenbaums”)
The new man in Etheline Tenenbaum’s life, her long-time accountant Henry doesn’t get a huge amount to do in “The Royal Tenenbaums,” but Danny Glover gives a lovely interior life to the man, ever-dignified in the face of Royal’s insults.
48. Bert Fischer (Seymour Cassel in “Rushmore”)
John Cassavetes staple Seymour Cassel was a regular in Anderson’s earliest movies, but found his best showcase in “Rushmore,” as Max Fischer’s sweet-natured barber father, who doesn’t quite understand his son and his eccentricities, but loves him all the same.
47. Mr. Bishop (Bill Murray in “Moonrise Kingdom”)
Perhaps the most muted of Murray’s creations for Anderson, Mr. Bishop is the neglectful father of lead Suzy, seemingly sunk into a deep depression and finding it difficult to care even that his wife is having an affair with the local cop. It’s not the actor’s finest hour, but he still elevates what he has.
46. Dirk Calloway (Mason Gamble in “Rushmore”)
Once the star of “Dennis The Menace” with Walter Matthau, Mason Gamble showed some deft comic chops as Max’s best friend (turned frenemy, turned friend again), who suffers the school curse of having a hot mom. He’s a marine biologist now! The actor, not the character.
45. Rosemary Cross (Olivia Williams in “Rushmore”)
Alluring teacher Rosemary doesn’t ever quite develop past being a prize for Max and Blume to compete over, but Olivia Williams brings both a melancholy and a spikiness to the character that makes her much more interesting on the page, and she’s got great chemistry with her co-stars.
44. Author (Tom Wilkinson/Jude Law in “The Grand Budapest Hotel”)
He’s mostly a framing device, certainly, but the unnamed Author of “The Grand Budapest Hotel” (played first by Tom Wilkinson, then Jude Law) makes a big impression, in large part because of the uproarious moment when Wilkinson yells at his son.
43. Dudley Heinsbergen (Stephen Lea Sheppard in “The Royal Tenenbaums”)
Coming straight from “Freaks & Geeks” (Sheppard played Harris on the beloved show), Dudley, the research subject of Bill Murray’s character, suffers amnesia, dyslexia and color-blindness, but does at least have great hearing. He’s a scene-stealer, even if the role is tiny.
42. Future Man (Andrew Wilson in “Bottle Rocket”)
So gigantic in size and stature that he seems like a specimen of perfection of the Future, the elder Mapplethorpe is a bully who incessantly picks on his sibling, but deep down, this ago dominance is a mask for his insecurity and need to connect.
41. Kylie (Wallace Wolodarsky in “Fantastic Mr Fox”)
Voiced by “Simpsons” screenwriter and long-time Anderson pal Wally Wolodarksy, Kylie is Mr. Fox’s super, his best friend/sidekick, and his personal assistant. Fiercely loyal but often disappearing into a trance, he’s the source of some of the film’s best absurdist gags.