It's been 25 years since Reese Witherspoon starred in the picture-perfect film; catch up with the actress and her castmates now
It's been 25 years since on-screen siblings Reese Witherspoon and Tobey Maguire were transported through the TV from the 1990s into the seemingly perfect world of the 1950s-era Pleasantville, which debuted on Oct. 23, 1998.
"I think we look on that time in the 1950s and say they were all so innocent and pure but really it was more about ignorance and not looking at reality and not wanting to face what was really happening with racism and segregation," Witherspoon said in an interview with Screen Slam. "It's about finding something inside you."
The cast included screen stars Joan Allen, Jane Kaczmarek and William H. Macy, in addition to Paul Walker, who died in November of 2013, JT Walsh, who died in 1998, and Don Knotts, who made his last on-screen appearance in Pleasantville before his death in 2006.
Here, on the film's milestone anniversary, catch up with some of the movie's stars, then and now.
Reese Witherspoon as Jennifer
Witherspoon was a fast-rising star when she joined the cast of Pleasantville, playing quintessential '90s teen Jennifer who gets taken into her TV alongside brother David thanks to a mystical television repairman played by Don Knotts.
In the years that followed, Witherspoon became one of the top actresses in Hollywood, moving onto other teen faves like Cruel Intentions and Election before jumping into Elle Woods' pink shoes for the Legally Blonde franchise. She won an Oscar in 2006 for playing June Carter in the Johnny Cash biopic Walk the Line.
The mom of three (she shares son Deacon and daughter Ava with ex Ryan Phillippe and son Tennessee with ex Jim Toth) now has her own production company, Hello Sunshine, and scored an Emmy nomination in 2022 for her work on The Morning Show.
Tobey Maguire as David
Like Witherspoon, Maguire had a string of teen hits to his name before he played her brother David in Pleasantville.
In the years since, he most famously wove Spider-Man's webs in the early 2000s version of the franchise, and scored a Golden Globe Award nomination for 2010's Brothers.
A dad of two kids with ex Jennifer Meyer, Maguire has since starred in several more critically acclaimed films, including The Cider House Rules, Seabiscuit and Babylon.
Jeff Daniels as Bill Johnson
Daniels' résumé was long even before Pleasantville, with standouts like Arachnophobia, Gettysburg and Dumb and Dumber to his name from his work in the '80s and '90s.
In this film, he portrayed soda fountain shop owner Bill Johnson, who falls for Jennifer and David's mom Betty in the alternate Pleasantville world.
Following the film, he continued his work on the big screen, earning a Golden Globe nomination for 2006's The Squid and the Whale. More recently, he's received accolades for his work on the HBO drama The Newsroom and the Netflix limited series Godless, scoring one Emmy for each.
He has three grown children with wife Kathleen.
Joan Allen as Betty
Allen was coming off back-to-back Oscar nominations for 1996's Nixon and 1997's The Crucible when she took on the role of Jennifer and David's mom Betty in Pleasantville.
She went on to favorites including The Notebook and The Bourne Legacy in addition to continuing her work on the stage. More recently, she's featured on television in series like The Family and Lisey's Story. All in, she has two Tony Award nominations, three Emmy nominations and three Academy Award nominations.
Allen has one grown daughter with ex Peter Friedman.
William H. Macy as George
As Jennifer and David's dad, Macy saw some of the harsher realities the changes of Pleasantville brought to his family.
Prior to the film, Macy had been acting since the 1970s, most notably earning an Oscar for his role in 1997's Fargo. He is a 15-time Emmy nominee, thanks to guest roles on ER and Sports Night and his acclaimed role as Frank Gallagher on Shameless.
Macy and wife Felicity Huffman share two daughters.
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