‘Pleasantville’ 25th anniversary: Remembering Gary Ross’ 3-time Oscar nominee

One of the most acclaimed movies of 1998 is “Pleasantville,” starring Tobey Maguire, Reese Witherspoon, Jeff Daniels, William H. Macy and Joan Allen. Written and directed by four-time Oscar nominee Gary Ross, the film is a creative fantasy drama about two 1990s teen siblings who are transported to a 1950s family sitcom and then slowly begin to transform the dull, colorless world into someplace better. Released 25 years ago in October 1998, “Pleasantville” only grossed about $50 million worldwide on a $60 million budget. But it did end up receiving three Oscar nominations. Read on for Gold Derby’s tribute to the “Pleasantville” 25th anniversary.

Most of the nation’s critics gave enthusiastic notices to “Pleasantville,” including Roger Ebert in the Chicago Sun-Times, who picked it as the second-best film of 1998 and wrote that it “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.” In addition, Caroline Westbrook said in Empire Magazine that it “proves Hollywood is still capable of turning out comedies that are as intelligent and original as they are feelgood.” And Derek Adams in Time Out wrote that the movie “playfully spoofs the small-minded lifestyle idealized by family values advocates, and the intolerance and insecurity underlying that ideal.”

With “Pleasantville” released to rave reviews in the fall of 1998, was the movie likely to be a major awards player despite its somewhat lackluster box office? Its biggest hurdle was going to be all the competition, including “Saving Private Ryan,” “The Truman Show,” “Shakespeare in Love” and “The Thin Red Line.” “Pleasantville” was completely overlooked at the Golden Globes — not a good sign — but then it did receive a Critics Choice Award nomination for Best Picture, and Joan Allen won the Best Supporting Actress trophy in a tie with Kathy Bates for “Primary Colors.” Allen had been Oscar-nominated in recent years for two films — “Nixon” and “The Crucible” — and her third Academy Award nom looked probable for “Pleasantville” for her spectacular performance as Betty, given she also won Best Supporting Actress from the film critics groups of Boston, Dallas-Fort Worth and Los Angeles.

However, Allen and the movie were snubbed at both SAG and BAFTA, and going into Oscar nominations morning, the chances of “Pleasantville” appeared dismal. With the actors not supporting “Pleasantville” at SAG, and BAFTA not giving the film any technical nominations, many could’ve been rightfully doubtful of the movie getting any noms at the Academy Awards. As expected, Allen didn’t make it into Best Supporting Actress for “Pleasantville” despite her Critics Choice win and multiple critics prizes, but the film did ultimately show up in three technical categories — Best Art Direction-Set Direction, Best Costume Design and Best Original Dramatic Score.

Did “Pleasantville” have a shot at winning anything at the 71st Academy Awards on March 21, 1999? I would argue odds were slim considering the overall lack of support for the movie in general. If “Pleasantville” could’ve received one nomination in the above-the-line categories, like Allen in Best Supporting Actress or Ross in Best Original Screenplay, then the film would’ve been more competitive in the technical noms it received.

In Best Art Direction-Set Decoration and Best Costume Design, “Pleasantville” was no match for “Shakespeare in Love,” the celebrated end-of-the-year period drama that became such a force throughout the 1999 awards season that it managed to overtake the modern war movie classic “Saving Private Ryan” in the Best Picture category, stunning many. With Judi Dench winning Best Supporting Actress for an eight-minute-long performance and Gwyneth Paltrow taking the Best Actress trophy, the immense love for this film was going to extend to the tech categories, as “Shakespeare in Love” claimed both Best Art Direction-Set Decoration and Best Costume Design. “Pleasantville” was likely in third place here at best, the more beloved “Elizabeth” also competing in both categories.

The only category “Pleasantville” had a fighting chance in was Best Original Dramatic Score for Randy Newman, back in that four-year period in the 1990s when the Academy split original score into two categories — Dramatic and Musical or Comedy. There wasn’t a major frontrunner in the Original Dramatic Score category that year, as “Elizabeth,” “Life is Beautiful,” “Saving Private Ryan” and “The Thin Red Line” competed with “Pleasantville” for the most votes. What Gary Ross’ film had going for it was that Newman was on his 10th and 11th Oscar nominations that year, the celebrated composer recognized for both “Pleasantville” and “A Bug’s Life.” If an overdue narrative for Newman had kicked into high gear at the right time, he likely could’ve won for one of those two movies that night, but ultimately the academy went with “Shakespeare in Love” in Original Comedy or Musical Score and “Life is Beautiful” in Original Dramatic Score.

Despite the film going home empty-handed at the Oscars, “Pleasantville” continues to be a stunningly original piece of motion picture entertainment 25 years later. The screenplay is innovative and surprising, the mix of black-and-white and color cinematography is seamless, and the performances are all outstanding, especially Allen in her lovely, emotionally devastating turn. In Variety, Joe Leydon wrote, “Ingeniously conceived and impressively executed, ‘Pleasantville’ is a provocative, complex and surprisingly anti-nostalgic parable wrapped in the beguiling guise of a commercial high-concept comedy.” I couldn’t have said it better myself.

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