Paul Giamatti and Thomas Haden Church Went Up Against Robert Downey Jr. and Matt Dillon for ‘Sideways’

The film Sideways became a surprise hit in 2004. Starring Paul Giamatti and Thomas Haden Church as two buddies going on a bonding weekend through wine country, the comedy-drama garnered Oscar noms for Church and co-star Virginia Madsen. The Wings alum reflected on landing the role and the A-listers who were in the running.

Paul Giamatti and Thomas Haden Church of 'Sideways'
Paul Giamatti and Thomas Haden Church of ‘Sideways’ | Jeff Kravitz/FilmMagic, Inc.

George Clooney wanted a role in ‘Sideways’

Director Alexander Payne received plenty of interest when he began casting for Sideways. With a list of impressive film directing credits to his name including Citizen Ruth, Election and About Schmidt, Payne was fielding offers from some of Hollywood’s biggest box office draws.

“I heard rumors that Brad Pitt and George Clooney were chasing it,” Church told Entertainment Weekly in 2018. “I heard the rumors and then after I was hired, I asked Alexander Payne, and he said yes.”

Payne met with Clooney about the project, where the actor shared that he wanted to team up with Pitt for Sideways. Though the director decided to go with lesser-known actors for the film, he later worked with Clooney on The Descendants in 2011.

“Clooney had even gone as far as taking him to lunch and saying ‘Look, you know, Brad and I have discussed it, I know that Brad’s also tried to get to you… This is a great opportunity for all of us to work together’,” Church explained of Clooney’s conversation with the director. “[Payne] just wanted to move onto his next project without there being these towering movie stars.”

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Robert Downey Jr. had his eye on ‘Miles’ character

Church had spoken with Payne about past projects but the two had yet to collaborate when the opportunity for Sideways came around. The George of the Jungle star recalled the remaining names on the short list for the cast.

“I knew Alexander,” Church said. “I’d met with him on Election, I’d met with him on About Schmidt. Then I flew in for what ultimately was a screen test [for Sideways]. There was four guys left. There was myself and Paul [Giamatti], Matt Dillon and Robert Downey Jr. Those were the other two finalists.”

Giamatti played the somber writer and wine enthusiast Miles, taking his partying – and engaged – pal Jack (Church) on a weekend before his nuptials. Church knew going in for his final reading that he had his work cut out for him.

“You want to talk about nerve-wracking,” the Oscar nominee remarked. “When I pulled in through security and I was sitting in my car waiting, I looked over and Robert Downey Jr. was sitting in his car going over his lines. I glance over, and there’s Matt Dillon sitting in his car going over lines. I’m like, ‘I’m here reading against one of these guys’. It ended up Robert Downey Jr. was going after Paul’s role, and Matt Dillon was going after mine.”

Thomas Haden Church tried out for several film roles before landing ‘Sideways’

Church was a familiar face on the small screen on sitcoms like Wings and Ned and Stacey before crossing over to films. He listed a number of parts he auditioned for with no results until Sideways came his way.

“I’ve certainly been the bridesmaid a number of times,” Church said. “I screen-tested for the lead in Ace Ventura, I screen-tested for Quiz Show, I screen-tested for Tom Sizemore’s role in Saving Private Ryan. I wanted to do that movie bad. Then again, Sideways was the only movie that I auditioned for in 2003.”

The actor went on to star in numerous films including Max, We Bought a Zoo, Easy A, and Marvel’s Spider-Man 3.

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