Sideways debuted in 2004 to critical acclaim, and it not only garnered attention and praise in the US but also became an international hit. Writers Alexander Payne and Jim Taylor won an Oscar for Best Adapted Screenplay, and the film also garnered two Golden Globes and a host of other prestigious awards.
The story centers on two buddies, Miles (Paul Giamatti) and Jack (Thomas Haden Church), who go on one last romp through California’s wine country before Jack gets married. The trip, of course, leads to a range of experiences neither expected.
So check out what Giamatti, Haden Church and the rest of the beloved characters from this sentimental comedy are up to now. Which character was your favorite? Tell us in the comments below.
Lovable loser Miles has many great scenes in the film. Who could forget him guzzling from a winery spit bucket or drinking his prized bottle of 1961 Château Cheval Blanc in a fast-food joint? But Paul Giamatti has, of course, gone to appear in dozens of films, including Cinderella Man, The Illusionist, The Hangover Part II and, more recently, 12 Years a Slave and Saving Mr. Banks. He’s also made TV appearances on 30 Rock and Downton Abbey, and won an Emmy and a Golden Globe playing our second President in the miniseries John Adams. Upcoming roles include supervillain The Rhino in The Amazing Spider-Man 2 and controversial therapist Dr. Eugene Landy in Love & Mercy, a film about Beach Boys front man Brian Wilson. Both are set to hit theaters this year.
Virginia Madsen hasn’t slowed down since her portrayal of Miles’ crush Maya. She’s appeared in movies like The Number 23, The Asronaut Farmer, The Haunting in Connecticut and the made-for-TV Hatfields & McCoys. She’s also done voice work for Cartoon Network’s Justice League and made appearances on TV shows including Monk, Scoundrels, Hell on Wheels and Witches of East End. She has multiple upcoming projects, including Walter, an indie dramedy about a young man who believes he’s the son of God, which co-stars William H. Macy, Neve Campbell and Milo Ventimiglia.
After playing cool motorcycle chick and Jack’s love interest Stephanie, Sandra Oh has gone on to appear in a slew of popular movies and television shows. She was in films like Hard Candy, Ramona and Beezus and Rabbit Hole and has done voice work on multiple TV cartoons, including Phineas and Ferb, Robot Chicken and American Dad! But she’s probably best known for her decade-long role as Dr. Christina Yang on ABC’s Grey’s Anatomy, which garnered her a Golden Globe and five Emmy nominations. When she appeared in Sideways, Oh was married to its director and co-writer, Alexander Payne, but the couple has since divorced.
Since playing the adulterous and fun-loving Jack, Thomas Haden Church has appeared in a variety of films, most notably Idiocracy, Spanglish, Easy A, We Bought a Zoo and John Carter. (Like Giamatti, he’s also played a Spider-Man villain: Sandman in 2007’s Spider-Man 3.) He’s had a handful of TV roles, including a leading part in the AMC miniseries Broken Trail with Robert Duvall. Later this year, he’ll appear with Greg Kinnear in Heaven is for Real and with Terrence Howard in Cardboard Boxer.
For most of Sideways, Miles is still hung up on his happily remarried ex-wife, played by Jessica Hecht. Since that role, Hecht has had no shortage of work. She’s appeared in films like The Forgotten, Dan in Real Life, J. Edgar and The English Teacher, and in bit roles on popular TV shows from ER and Law & Order to The Good Wife and The Forgotten. Breaking Bad fans will also recognize Hecht as Gretchen Schwartz, Walter White’s former love interest and co-owner of Grey Matter Technologies.
Missy Doty hasn’t been in many films since Sideways, in which her character Cammi has a one night stand with Jack (though she was in last year’s Oscar-nominated Nebraska). However, she’s been all over your TV screen, with roles including Nickelodeon’s iCarly, ABC’s Desperate Housewives and FOX’s Bones. She’s also had recurring parts on Showtime’s Shameless, HBO’s True Blood and FX’s American Horror Story.