- And Starring: Reese Witherspoon's billing.
- Anvilicious: A frequent complaint is that the movie isn't exactly subtle.
- Award Snub: Joan Allen won several critics awards for Supporting Actress yet didn't receive an Oscar nomination.
- Awesome Music:
- The Dave Brubeck Quartet's "Take Five", then Miles Davis' "So What" playing as David explains that there is a world outside of Pleasantville.
- Etta James' "At Last".
- Buddy Holly's music is used in the movie to good effect.
- Fiona Apple's cover of "Across The Universe" was particularly good ending music.
- Bellisario's Maxim: It's probably best not to think too deeply into the (most likely intentional) plot holes of the Pleasantville (the TV series) universe.
- Genius Bonus: The first two books that David fills in by explaining the plots of are The Adventures of Huckleberry Finn and The Catcher in the Rye, the two most banned books in American history.
- Hilarious in Hindsight:
- David is forced to pretend he's Bud Parker. Later on his actor, Tobey Maguire would play another man named Parker — Peter Parker of Spider-Man.
- Reese Witherspoon's character has a reputation for being a slut, before changing her life around and becoming college-bound. One year later she's a student engaged in a battle of wits with another slut.
- Retroactive Recognition: Paul Walker plays Jennifer/Mary Sue's boyfriend Skip Martin.
- Shallow Parody: Shows like Leave It to Beaver and The Andy Griffith Show were not nearly as gritty and dramatic as a more modern show, but they were hardly the surrealistically-perfect world Pleasantville is. The film more parodies the modern conception of older shows than the actual shows. In fact, it's likely that Pleasantville would have been cancelled as too boring as the show featured no conflict whatsoever.
- To clarify, in the time when a series such as Pleasntville would have been made, yes, Broadcast Standards and Practices very sharply limited what one could say, do or show on television. In the real world, that most archetypal of Fifties shows, Leave It To Beaver, had Beaver refer to swearing ("A man slipped on a rock and fell into the lake. He was so loud we got to hear almost everything he said") and once get in trouble from his teacher for swearing in the hall. An episode dealt with drunkenness, another one divorce, relations with a Hispanic family that's just moved in. Also things like losing sports teams, theft, con-men, bums, and bullies like Eddie Haskell or Lumpy Rutherford. A late episode even has "square" Wally date a fast girl. As icing on the cake, a couple of episodes dealt with classic boy's stories such as Tom Sawyer or Treasure Island. So the books in Mayfield definitely have words in them!
- Some Anvils Need to Be Dropped: One of the main messages of this movie is that while the world today may be a scary place and things have worsened in some aspects (as exemplified by the class montage in the beginning of the film), one should focus on how many more things improved, instead of wallowing in the "Good 'Ol" past. To quote Roger Ebert's review:"Pleasantville is the kind of parable that encourages us to re-evaluate the good old days and take a fresh look at the new world we so easily dismiss as decadent. Yes, we have more problems. But also more solutions, more opportunities and more freedom. I grew up in the '50s. It was a lot more like the world of 'Pleasantville' than you might imagine. Yes, my house had a picket fence, and dinner was always on the table at a quarter to six, but things were wrong that I didn't even know the words for."
- Strangled by the Red String: Averted. The points of the love triangle muse cheerfully at the end that they don't know what will happen.
- The Woobie:
- George after Betty leaves him.
- Bill. Especially when the greyscale mob destroys his diner and art, leaving him crestfallen.
YMMV / Pleasantville