Sandra Oh Was Only Briefly in This Movie, and She Still Stole the Show

The Big Picture

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• Sandra Oh’s performance as Stephanie in Sideways showcases her comedic talents and ability to portray a character with depth in a limited screen time.
• Stephanie and Jack’s relationship is filled with humor and a sense of impending doom, as their different perspectives and interests clash.
• Stephanie is one of the memorable female characters in Alexander Payne’s films, and Sandra Oh holds her own alongside industry heavyweights in this breakout role.

Although things have changed significantly as a result of the streaming era, there have been many great television stars that were never able to completely make the transition to film. Sarah Oh is a great example. Oh immediately established her range as a dramatic performer thanks to her breakout performance on Gray’s Anatomy, which led to a series of successful roles in other prestigious television projects. Although Oh was ruthless on Killing Eve, she was hilarious on The Chair; she hasn’t been able to be pinned to just one genre. Despite how strong Oh’s work on television has been, her film career has not been as successful. This says less about her abilities as an actress, and more about the lack of great roles written for women of color. Although her performances in Umma, Hard Candy, Tammy, and Under the Tuscan Sun were perfectly fine, they don’t showcase the same range and complexity that her television work does. However, Oh was given a brief role in Alexander Payne’s Academy Award-winning dramedy Sideways. Despite the brevity of her screen time, Oh is one of the most memorable aspects of the film.

Sandra Oh’s Stephanie Is an Experienced Wine Pourer in ‘Sideways’

Oh co-stars in Sideways as Stephanie, a wine connoisseur who works professionally in the Santa Ynez Valley wine country. Stephanie has made a career out of something people consider a luxury, and treats her duties as a wine pourer with gravity. Stephanie’s knowledge of expensive wine brands makes her an expert within her workplace, and attracts the attention of the soon-to-be-married man Jack Cole (Thomas Hayden Church). Jack is in the midst of a pre-wedding vacation with his best friend Miles (Paul Giamatti in one of his best roles), a wine aficionado with a passion for writing. Although Miles engages with Stephanie on an intellectual level, as they both have a borderline pretentious passion for wine, Jack’s interests are more romantic in nature. Jack masks his impending wedding from Stephanie, and the two begin a passionate affair together. Jack ensures that Miles is silent about the upcoming wedding; he’s so focused on spending time with Stephanie that he ignores his responsibilities.

There’s a sense of impending doom within Jack and Stephanie’s relationship. It’s obvious that whatever happiness they may have temporarily found together is untenable. Jack is about to be wed, and he can only keep his secret for so long. However, even if Jack wasn’t already bound to another partner, Stephanie is far too intelligent for him. She finds his curiosity and snarky sense of humor charming, but it’s not exactly the basis for a relationship. Oh does a great job at showing how Stephanie judges Jack; she greets all of his obnoxious comments with a generous smile, as if she’s trying to stop herself from lampooning him. Jack is so enamored with Stephanie that he doesn’t realize that she may be making fun of him. Church and Oh do a great job at showing how differently the two characters view their relationship. Jack imagines that Stephanie is the woman that he has spent his entire life looking for, as she seemingly shares all of his interests. However, Stephanie doesn’t see him as anything more than a passing fling. The specificity with which Oh depicts a character with such little screen time makes Sideways one of her most memorable performances.

Sandra Oh and Thomas Hayden Church Have Great Chemistry

Although Church has given more dramatic performances in the past, such as his scene-stealing role as Sandman in Spider-Man 3, Jack is one of his more eccentric roles. The same could be said for Oh; Stephanie’s open sociability and gregarious sense of humor couldn’t be any more different than Eve Polastri. Their relationship works as well as it does because it’s clear that both characters are buying into a fantasy version of reality. A job that consists entirely of pouring wine seems like a paradise to Jack. Even though it’s simply a job for Stephanie, Jack’s more fantastical ideas about their relationship allows her to temporarily accept how unique her profession is.

The relationship between Jack and Stephanie is even more hilarious in comparison to Miles. While Stephanie and Jack have been continuing their affair, Miles has been slowly developing a relationship with Stephanie’s friend, Maya Randall (Virginia Madsen). Compared to Jack, Miles is awkward, confrontational, and less romantic; Payne gets a hilarious downbeat performance out of Giamatti. The awkward interest that Miles shows for Maya is the complete opposite of how infatuated with each other Jack and Stephanie are. The exaggerated passion that Stephanie and Jack show for each other makes Miles feel even more isolated. In her limited capacity, Oh’s character was able to make Miles more compelling as a protagonist.

Stephanie Is One of Alexander Payne’s Better Female Characters

Although Sideways was an early role in Oh’s career, it signified that she could hold her own within a prestigious award season contender alongside industry heavyweights like Giamatti and Church. Payne has shown a great ability of identifying emerging talent and giving them breakout roles; Stephanie is just one example of a scene-stealing performance by a future star. Other standout female performances in Payne’ films include Shailene Woodley’s role as George Clooney’s daughter in The Descendants, Laura Dern’s career defining role in Citizen Ruth, and Reese Witherspoon’s character Tracy Flick in Election, which may be getting a sequel very soon.

Stephanie isn’t necessarily one of the leads in Sideways, but she does have one of the most memorable scenes. As is expected, Jack isn’t able to keep his engagement a secret, which inspires a complete meltdown from Stephanie. Her furious reaction brings Jack down to Earth, as he realizes that he’s been playing with fire. It’s a critical scene that forces both Jack and Miles to reflect on their priorities. It was also a great showcase for Oh’s comedic talents, especially when the film began to veer towards more serious territory. Oh’s performance is the embodiment of the phrase, “There are no small parts.” Just because she has a smaller role in Sideways doesn’t mean that it’s not one of her most underrated performances to date.

Sideways is available to rent or purchase on Apple TV+ in the U.S.

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