Looking back at Pleasantville, 20 years later

This year is the 20th anniversary of Gary Ross’s 1998 fantasy/comedy/drama Pleasantville, so what better time to revisit this classic film?

Our story begins with shy teenager David (Tobey Maguire) and what seems to be his awkward attempt to ask a girl out. We later realize that the girl in question is looking at another guy and this is David’s attempt at asking her out.


The school year is drawing to a close for both David and his twin sister Jennifer (Reese Witherspoon), which is why we next see a montage of various teachers from their high school basically telling the student body that there’s no chance in hell that great things are in store for them. Given that, it may be understandable why David finds solace in things such as television.

At the same time, the much more social Jennifer manages to get a date with a guy she’s pining for. Her mom is out of town, so they’re set to meet at Jennifer’s house. Of course, this is on the same night that David plans to spend time there watching a marathon of the Leave It to Beaver-esque sitcom Pleasantville. The astonishing part here is that the marathon is part of a trivia contest which awards the winner $1,000. Too bad there aren’t more marathons like these, as they may give shows that were given the axe too soon a chance to find more of an audience.

The two siblings fight over the remote, as Jennifer plans to watch a concert on MTV with her date. Naturally, this little scuffle results in the remote breaking with, apparently, no way to turn the damn set on manually (which is as dumb as the nitroglycerin bomb that can’t be turned off in Hollow Man).

But wouldn’t you know it, a TV repairman (Don Knotts) shows up at the door at that very moment. Although startled, the siblings welcome his help. The repairman’s ears perk up when David reveals his plans to watch the Pleasantville marathon. He asks David a few trivia questions about the show, and is happy when David answers them correctly.

The repairman takes out a bizarre-looking remote and says that it’ll “put you right in the show”. After departing, David turns the marathon on, which (what a surprise!) prompts Jennifer to try to wrestle the remote from him. At the same time, the two Pleasantville siblings Bud (Kevin Connors) and Mary Sue (Natalie Ramsey) Parker are seen fighting over a radio.

David and Jennifer are then sucked into the TV and take their places in the Parker living room, now in black and white and wearing the same clothes. The Parker patriarch George (William H. Macy) walks by, telling them to hurry up or they’ll be late for school.

The repairman addresses David and Jennifer via the Parkers’ TV and tells them that they are indeed in Pleasantville. He commends David on his knowledge of the show, saying that most people only know info about the show’s early years (which could actually be said for a number of long-running shows, when you think about it).

Jennifer is naturally pissed off because she still has that date, and the repairman doesn’t improve her mood when he shows her said date walking away from her house and calling her a bitch when nobody answers the door.

David begins imploring the repairman to send them back, but he darts off thinking David is being ungrateful. He adds that he’ll get back to them in a couple of weeks.

The twins are called to breakfast by Bud and Mary Sue’s mom Betty (Joan Allen), and she has a mountain of pancakes ready for them. Jennifer’s claims that she’s not hungry are met with laughter by her “parents”.

As they walk to school, David is astonished and Jennifer is disgusted by the wholesomeness that now surrounds them. He implores her to just play along until the repairman returns. Her mood lightens when she sees Skip Martin (Paul Walker), the captain of the school’s basketball team, the Pleasantville Lions.

At school, David quickly fills Jennifer in on the girls that Mary Sue hangs out with. In geography class, everyone gives Jennifer a WTF? look when she asks what’s outside of Pleasantville.

David is seen practicing basketball, with everyone, including him, always getting the ball into the basket. Skip asks David if he can ask his sister out. David recognizes this as a plot point from an episode and politely tells Skip that this is a bad idea. Skip is heartbroken, which causes him to actually miss the basket when he tosses up his ball in anguish. The coach and the other players also give a WTF? look as the coach tells them to stay clear of the ball, as if it were a live wire.

This leads David into begging Jennifer to go out with Skip so as not to really fuck things up, including their chances of getting home. Jennifer is skeptical though, and informs her brother that the books in the library are all blank, and that the firemen earn their checks by just getting cats out of trees, because nothing burns in this town. On top of this, Mary Sue’s friends come to her all giggly at the prospect of her dating Skip.

Jennifer dresses for her date, while David goes to Bud’s job at the soda shop. He apologizes for his tardiness to his boss Bill (Jeff Daniels), who says that he just kept wiping the counter when Bud didn’t arrive on time to cook the french fries and what-not.

Among the customers that begin to arrive are Skip and Jennifer. She annoys David by ordering “a salad with Evian water.”

Jennifer goes to the bathroom, but alas, this place has no toilets either (I trust her breakfast went down easily then). Mary Sue’s girlfriends burst in asking how things are going, with one of them thinking Skip will take her to Lover’s Lane. This leads to Jennifer basically dragging Skip out of the shop so he can take her there. David goes apeshit and flings himself over the counter begging Jennifer not to do what he knows she’s going to do.

Sure enough, at Lover’s Lane, Jennifer wastes no time getting into Skip’s pants.

David rushes home, but his “dad” George tells him that Mary Sue is getting older and she wouldn’t do anything rash (cue sitcom laughter). David/Bud’s boss Bill later arrives, saying that David’s early departure from work prompted him to do all the closing duties himself. David also notices that Bill and his “mom” Betty are making eyes at each other.

Jennifer returns, with David pissed off at her. She promptly tells him to piss off as she goes to bed. But that doesn’t stop him from reading her the riot act the next day, as her dalliance has led to the basketball team now sucking. Also, it seems that flowers and bubble gum are now being colorized. David says that Pleasantville is getting disrupted, but Jennifer says that it needs that kind of change, and even adds that she’s mortified by her brother because of how much he likes the way it was.

Soon, as David keeps searching the TV night after night for the repairman, other people are going through similar changes. Jennifer even gives her “mom” a little info about sex at one point.  And Lover’s Lane begins to live up to its name more and more.

Eventually, David becomes smitten with a local girl named Margaret (Marley Shelton). This may explain why, when the repairman does get in touch with him again, David tells him to piss off, even though the repairman insists he can give him a remote that can return things to the way there once were (you’d think Barney Fife would’ve thought this through a bit more before sending two kids to a strange new place against their will).

As the town literally becomes more colorful, some of the townspeople, led by mayor Big Bob (J.T. Walsh) attempt to stop the changes to not just their town, but to their wives and children, who are now becoming more independent.

Indeed, Betty eventually leaves George for Bill, who has himself become disenchanted with working at the soda shop every day, and he becomes an artist. He even paints a nude portrait of Betty on the window of the soda fountain.

Riots eventually erupt as people who are now “colored” are being harassed. A trial soon takes place, with David and Bill’s defense of their actions causing the mayor to no longer be black and white himself.

With everyone now becoming more accustomed to the new look of everything, Jennifer’s newfound love for reading has somehow prompted her to stay in Pleasantville to finish her education. David, on the other hand, decides to return home, although he promises Jennifer, Margaret, and Betty that he’ll return. After bidding all three of them farewell (with Margaret and Betty taking the news that he used a remote to travel into a fictional universe surprisingly well), David returns home. He finds that only an hour has passed since he and Jennifer left, but his mom (Jane Kaczmarek) is in the kitchen crying her eyes out, believing that her life is far from what she thinks it should be. But he assures her that it doesn’t have to be anything specific.

The dramatic turn the film takes is certainly admirable, with the undertones of repression making it unique. The cast is terrific, with Knotts the perfect choice as the repairman who sets the story into motion. Appropriately, the film was dedicated to J.T. Walsh, who died shortly after filming.

This film was praised by critics and quickly developed a cult following, although it didn’t do well upon its initial release. Perhaps this was because the trailer seemed to give off a comedic, satirical vibe much like the following year’s Galaxy Quest, which proved to be a smash at the box office. However, the dramatic turns of Pleasantville likely caught audiences off guard, which may be why it didn’t rake in the cash like other films of 1998, including the great Saving Private Ryan and the headache-inducing Armageddon.

My only question is, what will David tell his mom when she asks about Jennifer? Somehow, I doubt “Mr. Furley gave us this bogus remote that zapped us into the show Pleasantville. One thing led to another and Jennifer decided to stay there” is going to cut it.

Rob Kirchgassner

Rob is a blogger, critic, and author. His latest novel is Ailurophobia, available now from Amazon.

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