20 Years Later, the Cast of ‘Sideways’ Has Aged Like a Fine Wine

SIDEWAYS, Sandra Oh, Thomas Haden Church, Virginia Madsen, Paul Giamatti, 2004,
© Fox Searchlight /courtesy Everett Collection

A weeklong road trip through California’s wine country in 2004’s beloved Sideways taught us a lot of things, including what “quaffable” meant and to stay away from Merlot. The Academy Award-winning film was the movie that had everyone talking about pinot noir and second chances. The story of two longtime friends — Miles and Jack (Paul Giamatti and Thomas Haden Church) — and the women they meet (Virginia Madsen and Sandra Oh) on a tour of California’s wine country is still refreshingly human, awkward and funny 20 years later.

“It’s the 20th anniversary of Sideways, so there’s all these Sideways events going on, and I don’t drink wine, but a lot of wine tastings are going on,” Madsen tells us when talking about the film in a recent interview. “I appreciate how people regard that film. It has a really special place in their hearts. It was such a cultural phenomenon.”

The film debuted in the U.S. on Oct. 22, 2004. Where are the stars today and what have they shared about the film? Find out below.

Paul Giamatti (57)

SIDEWAYS, Paul Giamatti, 2004,

Fox Searchlight/courtesy Everett Collection

From Cinderella Man, John Adams and Too Big to Fail to his 2023 role in the Oscar-nominated The Holdovers and in Showtime’s brilliant Billions as Chuck Rhoades, the two-time Oscar nominee’s resumé is one that A-listers envy.  Next up for Giamatti is reprising his roles as Harold Levinson in Downton Abbey 3 and as Dr. Lawrence Hayes in San Andreas 2, currently in development.

NEWARK, NEW JERSEY - JULY 26: Paul Giamatti takes part in a conversation with Stephen Colbert during the 2024 North To Shore Festival at New Jersey Performing Arts Center on July 26, 2024 in Newark, New Jersey.

Michael Loccisano/Getty Images

In an interview with Giamatti years ago, we talked about Sideways and asked about his real college roommates at Yale (Thomas Haden Church played his roommate in Sideways). He shared: “I had a bunch of roommates. They were great. I had three guys who were all just a bunch of shaggy, weird guys like me. One was a football player, one was a mountain climber and one was a writer. The football player was the last guy you’d expect to be a football player but he was great.”

Thomas Hayden Church (64)

SIDEWAYS, Thomas Haden Church, 2004,

Fox Searchlight/courtesy Everett Collection

With his trademark grin and his voluminous voice, Thomas Haden Church commands attention with just a simple greeting. With a resumé that dates back to six seasons starring as the lovable but clueless Lowell Mather in the 1990s NBC sitcom Wings, followed by his role as Ned Dorsey opposite a young Debra Messing (Will & Grace) in Ned and Stacey, plus numerous film credits to his name, it’s surprising that it wasn’t until his Oscar-nominated performance in Sideways that Church finally got some recognition.

“I was actually queued up to direct a movie from FOX [when] I was sent the script for Sideways. I was really going in a whole other direction but enjoying it immensely,” Church told us years ago. “I love working with actors, love directing actors and love being the answer guy. Not from a provincial, baronial standpoint; I just enjoyed being the answer guy from the start of the workday to the end of the workday, whether it was during casting, scouting, prep or shooting. I just liked being the guy.”

ACCIDENTAL TEXAN, (aka CHOCOLATE LIZARDS), Thomas Haden Church, 2023.

Jalisco Wayne/Roadside Attractions/Courtesy Everett Collection

Thankfully, Church gave being “the guy” in front of the camera versus behind it another chance. “I don’t think I could have gotten Sideways if I wasn’t prepared from everything that had gone on in the previous 14 years of my career. It wasn’t so much that when I read the script and met with them, it was like, ‘This is the moment, this is the big chance at 41 to resurrect my career,’” Church said of his performance. “But, thank God I was smart enough to recognize a good acting opportunity.”

Over the last 20 years he’s continued to find good opportunities, including in the Spider-Man franchise as the Sandman in 2021’s No Way Home; in the HBO series Divorce; as Stone in 2023’s TV series Twisted Metal; and next up, in the third installment of the Knives Out trilogy, Wake Up Dead.

Virginia Madsen (63)

Madsen was just 22 when she got her first big break in the Rob Lowe and Jacqueline Bisset 1983 hit Class. Her breakout role followed when she got cast in David Lynch’s  Dune (1894) as Princess Irulan. Other roles quickly followed from  Candyman (1992), The Prophecy (1995) and Ghosts of Mississippi (1996) to TV series like American Gothic and the short-lived CW horror Swamp Thing.

Next up for Madsen is the new series Holidazed on Hallmark+, where she stars opposite John C. McGinley (Scrubs) as the matriarch of one of the six families who live in the same cul-de-sac as they experience various challenges during the holiday season. The first two episodes of the series debuts November 14, with new episodes airing Thursdays.

John C. McGinley and Virginia Madsen in Holidazed on Hallmark+

When we talked to Madsen this past summer she had just watched Sideways again. “It’s kind of like watching a home movie because of the atmosphere that was created by Alexander [Payne] while we were shooting.”

Her favorite scene in the film is when all four of them were on the hill, and it’s actually the first scene they all did. “The camera was very, very far away, so we didn’t even know when it was running. And Alexander was kind of waving to keep going. And the hills turned silver and gold at sunset. We only had about 15 minutes, but it felt like an hour or two just sitting there having a picnic with them, laughing going, ‘Can you believe this job? This is the greatest job,’” Madsen says. “It’s very present for me, those memories. Not every movie is like that.”

Sandra Oh (53)

SIDEWAYS, Sandra Oh, 2004.

Fox Searchlight/courtesy Everett Collection

Sandra Oh, who was married to Sideways writer-director Alexander Payne (2003-06), immediately followed up her Sideways role as Stephanie with her long-running, Emmy Award-winning turn as Dr. Christina Yang on Grey’s Anatomy (2005-14), and then as Eve Polastri in the critically-acclaimed BBC America series Killing Eve, where she became the first Asian actor ever to receive a Best Actress Emmy nomination.

Next for Oh: Master of None‘s Aziz Ansari‘s comedy Good Fortune, and starring opposite Julianne Moore and Kyle Chandler in Margaret Atwood’s revenge thriller Stone Mattress.

LOS ANGELES, CALIFORNIA - OCTOBER 19: Sandra Oh attends the Academy Museum of Motion Pictures 4th Annual Gala in Partnership with Rolex at Academy Museum of Motion Pictures on October 19, 2024 in Los Angeles, California.

Emma McIntyre/Getty Images for Academy Museum of Motion Pictures

 

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