''Wonder Boys'' is a 2000 comedy-drama film written by Creator/SteveKloves and directed by Creator/CurtisHanson. Based on the [[Literature/WonderBoys 1995 novel]] by Creator/MichaelChabon, it revolves around Pittsburgh college professor/novelist Grady Tripp (Creator/MichaelDouglas) who, over the course of a weekend, has to handle a troubled student (Creator/TobeyMaguire), his unfinished novel (also called ''Wonder Boys''), his pregnant girlfriend (the chancellor of the college and his boss' wife), a purloined jacket and a dead dog.

The film also stars Creator/KatieHolmes, Creator/RobertDowneyJr and Creator/FrancesMcDormand. It was nominated for three UsefulNotes/{{Academy Award}}s and earned Music/BobDylan a Best Original Song Oscar for "Things Have Changed."

!!This movie contains examples of:

* BiTheWay: Terry Crabtree.
-->'''James''': So your friend Crabtree, is he... Is he gay?
-->'''Grady''': Most of the time he is, James. Sometimes he isn't.
* ConsummateLiar: [[spoiler:James Leer.]]
* {{Doorstopper}}: Grady's 2000+ page book.
-->'''James''': Is... ''all of that'' single space?
* EruditeStoner: Grady.
* EvilDetectingDog: Sara's husband is clueless about her affair with Grady. His blind(!) dog, Poe, on the other hand...
* {{MacGuffin}}: Marilyn Monroe's jacket.
* OnlyKnownByTheirNickname: Vernon Hardapple.
* ParentalAbandonment: [[spoiler:James tells Grady his parents are dead and he's being raised by his grandparents.[[ConsummateLiar Or not]].]]
* ShootTheDog: [[spoiler:Literally. Poe had it coming, though.]]
* SleepingDummy: [[spoiler:Poe finally comes in handy]].
* ThinkingOutLoud: James narrates as he's carried out of an auditorium.
-->'''James''': The doors made so much noise!
-->'''Grady''': Is he all right?
-->'''James''': It was so embarrassing! He had to be carried out.
-->'''Terry''': He's fine. He's narrating.
-->'''James''': They were going to the restroom. But would they make it in time?
* TeacherStudentRomance: Hannah Green wants to start one with Grady. He's tempted.
* ToughActToFollow: InUniverse. Grady's previous book ''The Arsonist's Daughter''.
* TrophyRoom: Walter's sports memorabilia closet.
* WholesomeCrossdresser: Miss Antonia Sloviak.
* WorldOfSnark
* WritersBlock: Subverted. Grady can't ''stop'' writing.
* YourCheatingHeart: Grady's had a long-standing affair with Sara. [[spoiler:James implies he's the product of an affair between his mother and his paternal grandfather. [[ConsummateLiar Or not]].]]