While there are many “suspension of disbelief” moments to be had in Gary Ross’ 1998 film, Pleasantville (including how Betty and George didn’t know what sex was—what? Did they think Bud and Mary Sue “just appeared” one day, fully formed?), perhaps the most nagging one is what actually happened to Jennifer a.k.a. Jen (Reese Witherspoon) when she decided to “stay behind” in Pleasantville. Ultimately meaning: staying behind in time, in the 50s realm within which Pleasantville exists. With David (Tobey Maguire) and Jennifer having gone back forty years, Jennifer was the sibling most horrified by the prospect of being stuck in such a stifling and repressive decade. Especially right when she was “getting really popular,” as she phrases it.
Naturally, a large part of that popularity was cultivated by her “sluttiness.” A brand she has no problem embracing by agreeing to fool around with Mark Davis (Justin Nimmo), who she invites over to her house via the announcement that her mom is going to be out of town for the weekend. This after an exchange between Jen and her friends dissecting her brother as follows: “Oh my God, he’s, like, so pathetic. I can’t believe you’re related to him.” Jen vacantly counters, “Only on my parents’ side.” Her friend adds, “Yeah, but you guys are like twins and stuff. You must be from the cool side of the uterus.” And that’s when Mark approaches for Jen to make her move, showcasing a coquettish line of the day to reel him in: “So you gonna watch the concert on MTV tonight?” Of course he is. This is the 90s. And MTV is still championing music as opposed to whatever it’s “offering” now.
Unbeknownst to Jen, however, David has other “grand plans” for the living room, all set up to watch the twenty-four-hour Pleasantville marathon. Having already “studied up” for the trivia questions that might be asked in exchange for the one-thousand-dollar prize giveaway, nothing is going to stop David from participating in the marathon (a.k.a. “watching his stories”)—least of all Jen’s “social emergency.” As they start to fight over the remote, the inevitable happens and it bursts out of both their grips, crashing to the floor and breaking apart. It’s a break that signals an impending fissure in the space-time continuum. In some sense, too, this is the kind of schism in events that creates the premise for other time travel narratives like Dark, or even Back to the Future (the quintessential “OG” of time travel movies).
“Fortunately,” after the incident, a TV repairman (played, all too appropriately, by The Andy Griffith Show alum Don Knotts) “just so happens” to be lying in wait outside in his van. Even though they should be sketched out by his sudden appearance, they’re too desperate for their TV to operate again to really question it. Thus, the “repairman” provides them with an extra special remote—one that has more “oomph.” As the duo reverts right back to fighting over it, they’re zapped into the TV as they continue to argue, once again, over who should have control of the programming, therefore dominion over the living room. Of course, it doesn’t much matter with the two now being stuck in Pleasantville, which might as well be called Squaresville, USA for as much fun as Jennifer is going to have in it. Or so she thinks until she catches sight of basketball captain Skip Martin (Paul Walker) driving by with his chiseled jaw and swoon-worthy smile.
All at once, Jennifer thinks that maybe life in black and white might be more manageable than she thought—until she learns that people view things that way metaphorically in addition to literally. Something she finds out thanks to David telling her re: “being sexy,” “They just don’t notice that kind of thing around here.” This is said to her after she’s already armed herself with about three pounds of underwire—enough to make her feel like she could kill a man with how pointy her tits are. And “killing” Skip is essentially what she does by giving him the “little death” called orgasm for the first time.
Once the rest of the school’s teens hear about what was really meant to be happening at Lovers’ Lane all along, people begin to burst into color left and right. And yet, Jen, despite all the sex she has, never does. Leading David to posit, “Maybe it’s not just the sex.” In other words, maybe it’s about having something awakened inside of you that never has been before. For Jen, that awakening actually happens to stem from academia—and, more to the point, apprehending that boys are a waste of her time and talent. As a result, she doesn’t turn into color until after the night she rebuffs a fuck date with Skip in favor of studying instead. Something she never would have done as a 90s girl. Which is somewhat ironic as that was a peak time for anti-male, Bikini Kill feminism. Her sudden color transformation might also be part of the blanket shift over the town after it experiences rain for the first time. Followed by a huge rainbow that appears over Pleasantville. Because, like Dolly said…
As those still comfortable in their black-and-white coma begin to grow more and more fearful of what’s happening, the very thing that Ray Bradbury warned about in Fahrenheit 451 begins to transpire, complete with a book-burning rally. During which Skip tries to steal Jennifer’s copy of Lady Chatterley’s Lover away from her, prompting her to decry, “This is like the only book I’ve read in my whole life, and you’re not gonna put it on that fire!” Clearly, her brief stint in Pleasantville has made her see her intellectual worth in a manner that she never did before. And it’s opened her eyes to all the possibilities she’s been missing out on by ignoring her cerebral worth. The irony is not lost on the viewer, who can distinctly remember her saying angrily to her brother at the beginning of arriving in Pleasantville, “We’re, like, stuck in Nerdville. I knew you’d pay a price for this. I knew you couldn’t be so hopelessly geek-ridden for so long without suffering some really tragic consequences.”
By the end, she trenchantly admits, “You turned into a pretty cool guy, how’d that happen?” Maybe it happened because she herself became the “nerd” she always loathed/never imagined she could become. And yet, here we have the problem of the fracture in the space-time continuum occur when Jennifer decides to stay behind to continue pursuing her academic betterment.
At the end, David asks, as though it’s really a viable choice, “You sure you don’t wanna come home?” She insists, “Yeah. I gotta do this for a little while.” But what is “this,” ultimately? Apart from living her life under the assumed name of a person who’s not even real? Her only logic for doing so being, “Besides, you even think I have a chance of getting into college back there?” Accepting her reasoning without suggesting that this might cause big issues in the future a.k.a. their present, David asks, “Do you have your admissions letter?” “Yeah, it’s right here.” She takes a pause before adding, “I did the slut thing, David. It got kinda old.” How very Pleasantville of her indeed. To add to the barrage of questions about how this would ever work, David assures, “I’ll come back and check on you soon.” It seems highly unlikely that he would be able to flit in and out of realms without the TV repairman eventually reclaiming his remote (even though he does look rather “good-natured” about it in his final frame). What’s more, why does their mother not seem to care at all that Jen is nowhere to be found? Apart from being overly preoccupied with her histrionics about not feeling comfortable taking a long weekend getaway with a younger man.
Getting on a bus that looks like the one pulled straight from the scene in Ghost World where Enid finally boards her own spectral, seemingly time machine-like vehicle, we have to wonder: will Jen go through all four years of college and return to the present with a degree showing that she graduated in 1962 in a discipline that isn’t even called what it once was? Who can say? All we’re meant to assume is that Jen is at last taking the time to focus on herself and what she wants, in lieu of throwing her body at any guy she thinks might help her social standing. Regardless of what difficulties that might cause if she ends up “slipping” and conceiving a child in the mid-twentieth century. Yes, come to think of it, this really does reek of the time travel issues that occurred in Dark, with an ouroboros of complications created by one “innocuous” move.