These are what we call the 'YMMV items.' Things that some people find in this work. We call them 'your mileage might vary' because not everyone sees these things in the same way. This starts discussions in the trope lists, a thing we don't want. Please use the discussion page if you'd like to discuss any of these items.
Dave Brubeck'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.
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.
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.
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.
Unfortunate Implications: Some critics wondered why the monochrome motif was even necessary, and why the same effect couldn't be achieved by replacing Bud and Mary Sue with teenagers of different, non-white races in the real world.