Tobey Maguire and 'Pleasantville' Cast 21 Years after the Movie Premiered

The comedy fantasy film was initially a box office bomb, but it eventually grew a cult following, especially since a couple of today’s big stars had their breakthrough in it. This is what has become of its cast.

“Pleasantville” was the first film directed by American writer, director, and actor Gary Ross, who also wrote the screenplay. He went on to direct the critically acclaimed “Seabiscuit” (2003) and the fan-favorite “The Hunger Games” (2012).

But before he reached the heights of Hollywood’s recognition, Ross trusted the amazing ensemble cast of “Pleasantville” his reputation as a director in 1998, and thanks to their hard work, the film is still as relevant as ever.

TOBEY MAGUIRE

The 44-year-old actor played David, the introverted high school student that is obsessed with the fictional 1950’s sitcom “Pleasantville,” and ends up inspiring a revolution in the supposedly dreamy black-and-white world.

Tobey Maguire. I Image: Getty Images.

Tobey Maguire. I Image: Getty Images.

Maguire continued to escalate positions in Hollywood after starring in the film, landing roles in “The Cider House Rules” (1999) and “Wonder Boys” (2000), before becoming a superstar by playing “Spiderman” from 2002 to 2007.

Besides his most famous role, Maguire has been in “Seabiscuit” (2003), “The Good German” (2006), and “The Great Gatsby” (2013). His last leading role to date was in 2014’s “Pawn Sacrifice.”

REESE WITHERSPOON

The 43-year-old actress played Jennifer, David’s twin sister, whose fight with him ends up with a broken remote control to fix, which inadvertently sets the entire surreal story in motion.

Reese Witherspoon. I Image: Getty Images.

Reese Witherspoon. I Image: Getty Images.

Since starring in the film, Witherspoon has led the most impressive acting career. In 1999, she caught attention by starring in the erotic drama “Cruel Intentions,” followed by 2000’s “American Psycho,” opposing Christian Bale.

In 2006 she won a Best Actress Academy Award for portraying June Carter in “Walk the Line,” and was nominated again in 2015 for “Wild.” She has been part of the cast of TV series “Big Little Lies” since 2017.

JEFF DANIELS

The 64-year-old actor played Bill Johnson, the soda fountain owner that becomes David’s boss in Pleasantville when he assumes the identity of the sitcom’s character Bud Parker. Bill discovers that his true passion is art.

Jeff Daniels. I Image: Getty Images.

Jeff Daniels. I Image: Getty Images.

Daniels was well known when he appeared in the film, and he has continued landing roles in both TV and film regularly, including roles in “My Favorite Martian” (1999), “Blood Work” (2002) “The Hours” (2002), “Infamous” (2006), and “Steve Jobs” (2015).

In 2018, he won his second Emmy award for playing Frank Griffin in the TV Western series “Godless.” His last film role to date was in “Guest Artist” (2019), which he also wrote.

JOAN ALLEN

The 63-year-old actress played Betty Parker, whose life turns upside down when she learns about the pleasures of life beyond their controlled surroundings, finding her true love in the process.

Joan Allen. I Image: Getty Images.

Joan Allen. I Image: Getty Images.

Since appearing in the film, Allen has enjoyed regular work in the industry, landing roles in “The Contender” (2000), “The Bourne Supremacy” (2004), and in the series “Luck” (2012), and “The Killing” (2014).In 2015, she played a supporting role in the Academy-Award nominated “Room,” and her last role to date was in 2016 in the TV series “The Family.”

WILLIAM H. MACY

The 69-year-old actor played George Parker, the patriarch of the fictional family that stars in the sitcom, who becomes enraged with the outsiders “coloring” his previously quiet town and causing his wife to leave him.

William H. Macy. I Image: Getty Images.

William H. Macy. I Image: Getty Images.

After the film, Macy went on to give one of his best performances in “Magnolia” (1999). Then, he played the lead role in “Panic” (2000). In 2003, he was in the Academy Award-nominated “Seabiscuit,” also starring Maguire.

On TV, Macy continued playing Dr. Morgenstern in “E.R.” until 2009. He also voiced The Narrator in “Curious George” (2006-2007). Since 2011, he has been part of the cast of “Shameless.”

J.T. WALSH

The late actor played Big Bob, the mayor of Pleasantville, who declares war against the “coloreds” for fears about their innovative ways going against the status quo.

Walsh had led a prolific career before playing the bad guy in the film and was known for military films like “Good Morning, Vietnam” and “A Few Good Men,” but he sadly passed away in 1998, the same year when “Pleasantville” premiered.

In 1999, he appeared posthumously in his last film “Hidden Agenda,” playing the character Jonathan Zanuck.

DON KNOTTS

The late actor played the mysterious TV repairman that gives David and Jennifer the magical remote control that takes them to Pleasantville against their will.

Don Knotts.I Image: Getty Images.

Don Knotts.I Image: Getty Images.

Knotts became a comedy legend in the 1960s, especially for starring in “The Andy Griffith Show” from 1960 to 1968, but he kept working regularly until his passing in 2006, aged 81.

“Pleasantville” was his last film appearance, with the exception of his voice work in 2005’s “Chicken Little,” on which he played Mayor Turkey Lurkey, but he made appearances of several TV shows until the last year of his life.

JANE KACZMAREK

The 63-year-old actress played David and Jennifer’s mother, who waits for her children back in the real world and finds out that her daughter chose to live her life inside a TV show from the 1950s.

Jane Kaczmarek. I Image: Getty Images.

Jane Kaczmarek. I Image: Getty Images.

Following her role in the film, she famously starred in the TV series “Malcolm in the Middle” from 2000 to 2006, and has continued working in the small screen with roles in “Wilfred” ( 2011), “Law and Order: SUV” (2013), and “The Middle” ( 2012-2013).

She was a regular in “Us & Them” (2013-2014). As a voice actress, she played Judge Constance Harm in “Los Simpsons” (2001-2010). Kaczmarek's last appearance to date was in the series “Carol’s Second Act” (2019).

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