Here's What The Cast Of “Pleasantville” Looks Like 20 Years Later

Then: Tobey Maguire has been working in the business since 1989 (and galavanting around town with his BFF, Leonardo DiCaprio) but his big breaks came around the time of Pleasantville. He appeared in Fear and Loathing in Las Vegas in ’97 and The Cider House Rules in ’99, but things really took off in ’02 when he was cast as the first in a long line of Spider-Men.

Now: Tobey is laying low as an actor these days, last seen (well, heard) as the Narrator/Adult Tim in 2017’s The Boss Baby. In 2014, he starred in the hilarious The Spoils of Babylon and played Bobby Fischer in Pawn Sacrifice. However, the former Spidey is thriving as a producer. He’s attached to four upcoming films, including the sixth Die Hard installment, McClane. He hasn’t tweeted since promoting The Great Gatsby in 2013, so his day-to-day is anyone’s guess!

Then: Pleasantville kicked off a great streak for America’s sweetheart, Reese Witherspoon. In 1999, she starred in Cruel Intentions and Election, which earned her a Golden Globe nomination. In 2000, she appeared in American Psycho and in two episodes of Friends as Rachel’s sister, Jill. A year later, she stole our hearts as Elle Woods in Legally Blonde.

Now: We all know Reese is killing it. She was nominated for an Emmy for her role in Big Little Lies last year, and recently appeared in A Wrinkle in Time. She has a ton of projects in the works, including Legally Blonde 3 (yay!), a live-action Tinker Bell movie, and (brace yourselves) an untitled TV project with Jennifer Aniston!

Then: A veteran actor of stage and screen, Wiliam H. Macy was thriving in the late ’90s. A year before Pleasantville, Macy was nominated for an Oscar for his role in Fargo AND nominated for an Emmy for his guest appearance on ER. In 1998, he appeared in multiple television shows including The Lionhearts, played Milton in the Psycho remake, and was featured in A Civil Action.

Now: Macy has been starring in Shameless since 2011, which has earned him five Emmy nominations in a row. Last year, he could be seen in the films Krystal and Dial a Prayer. He also recently celebrated 20 years of marriage to his awesome wife, Felicity Huffman.

Then: Easily the best part of Pleasantville, Joan Allen was another busy bee in the late ’90s. In 1997, you could see her in The Ice Storm and Face/Off. She was also nominated for two Oscars in a row: one for her role in 1996’s The Crucible and one for 1995’s Nixon.

Now: In 2016, Allen starred in the short-lived drama, The Family. Before that, she was last seen in the Oscar-winning film Room alongside her former onscreen husband, William H. Macy.

Then: Two years before Pleasantville, Jeff Daniels played Roger in the live-action 101 Dalmatians. He could also be seen in Trial and Error in ’97 and My Favorite Martian in ’99.

Now: Daniels is having a great 2018. He was nominated for two Emmys, winning one for his role in Godless (watch him thank a horse here). He was also nominated for The Looming Tower, which you can catch on Hulu. Next year, you can see him in the drama Guest Artist, which he also wrote.

Then: A year after playing Tobey’s love interest in Pleasantville, Marley Shelton went on to play Kristin in Never Been Kissed and Natalie in The Bachelor.

Now: Shelton has been working consistently since 1998, most notably starring in Planet Terror in 2007. She co-starred in Rise earlier this year, which was recently cancelled by NBC. She was also featured in the 2018 film Rampage alongside The Rock.

Then: Pleasantville was one of many late ’90s/early ’00s movies that featured Walker has a heart throb. He made Varsity Blues and She’s All That in 1999 and made his first appearance as Brian O’Conner in The Fast and the Furious in 2001.

Now: Walker died tragically in 2013. He passed during the filming of Furious 7, which was completed by using his brothers as stand-ins. He’s pictured right at the Fast & Furious 6 World Premiere in May 2013. Throughout his career, Walker won multiple awards, including two MTV Movie Awards and two Teen Choice Awards, proving him to be a consistent fan favorite.

Then: If you look closely enough, you can spot Danny Strong sprinkled throughout the town of Pleasantville. The year before, he made his first appearance as Jonathan Levinson on Buffy the Vampire Slayer, a role he would continue playing until the show’s final season. He also had a recurring role on the Clueless TV series and in 2003, he joined the cast of Gilmore Girls and was featured in Seabiscuit alongside Tobey.

Now: Strong is all over Hollywood, even winning an Emmy in 2012 for writing Game Change. He also wrote Lee Daniels’ The Butler, both Mockingjay films in The Hunger Games franchise, and has written multiple episodes of Empire, for which he is the co-creator. Currently, you can see him on Billions and in Tarantino’s upcoming film, Once Upon a Time in Hollywood.

Then: Pleasantville or Sunnydale? Marc Blucas, another Buffy-alum, can be spotted strutting his charm throughout the entirety of this movie. This was one of Blucas’ first films, previously making appearances in Eddie and Dilemma. In ’99, he also appeared in an episode of the Clueless series and made his first appearance as Riley Finn in Buffy.

Now: Blucas is still all over TV, recently appearing in Underground and Dietland. He recently starred in the Hallmark movie Season for Love and will be seen in the upcoming ABC drama The Fix.

Then: Jenny Lewis was only in Pleasantville for one scene, but this is a big deal since it was the same year Rilo Kiley — aka the greatest band in history — was formed. Lewis dabbled in Hollywood throughout the ’80s and ’90s, most famously appearing in an episode of Golden Girls in ’87 and co-starring in Troop Beverly Hills in ’89.

Now: Jenny is still making kickass music. Her most recent solo album, The Voyager, was released in 2014 and her newest band, Nice as Fuck, released a debut album in 2016. She was last seen onscreen in A Very Murray Christmas in 2015.

Then: J.T. Walsh was constantly working in the late ’90s, having been featured in six movies and TV movies in 1996 alone. From ’96-’97, Walsh played Capt. Frank Bach on Dark Skies.

Now: Sadly, Walsh died in February of 1998, before Pleasantville was even released. Not only was Pleasantville dedicated to the beloved actor, but so were his other two final films: The Negotiator (pictured right) and Hidden Agenda. Jack Nicholson also dedicated his Oscar for As Good as It Gets to Walsh’s memory. Walsh was nominated for an Emmy posthumously for his role in the TV movie Hope.

Then: Best known for playing Barney on The Andy Griffith Show and Mr. Furley on Three’s Company, Don Knotts was the perfect choice to play the TV Repairman. In the late ’90s and early ’00s, he made many TV appearances and lent his voice to multiple cartoons and video games.

Now: Knotts passed away in 2006 at the age of 81. He provided his voice to multiple projects in his final year, but was last seen onscreen in an episode of That ’70s Show in 2005. During his career, Knotts won five Emmys for playing Barney Fife.