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

While things have changed significantly with the advent of the streaming era, there have been many great TV stars who never made the full transition to film. Sarah O this is a great example. Oh immediately established herself as a dramatic performer with her outstanding performance on Gray’s Anatomy, which led to a series of successful roles in other prestigious television projects. Although O was ruthless Killing Eveshe was funny Chair; it could not be tied to one genre. Despite how strong Oh’s work was on television, her film career was not as successful. This speaks less to her abilities as an actress than to the lack of good roles written for women of color. Although her performances in Umma, Caramel, Tammy, And Under the Tuscan sun were perfectly fine, they don’t show the same variety and complexity as her television work. However, Oh was given a short role in Alexander PayneAcademy Award-winning drama Sideways. Despite her brief screen time, “O” is one of the most memorable aspects of the film.

Image via Fox Searchlight Pictures


Two middle-aged men with little to show but disappointment embark on a week-long road trip through California wine country just as one of them is about to head down the aisle.

Date of issue
October 22, 2004

Alexander Payne

Paul Giamatti, Thomas Haden Church, Virginia Madsen, Sandra Oh, Marylouise Burke, Jessica Hecht

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Sandra Oh’s Stephanie is an expert wine pourer in Sideways.

Oh co-stars Sideways as Stephanie, a wine connoisseur working professionally in the Santa Ynez Valley wine country. Stephanie has made a career out of what people consider luxury.and takes his responsibilities as a wine bottler seriously. Stephanie’s knowledge of high-end wine brands makes her an expert in her workplace and attracts the attention of soon-to-be-married Jack Cole (Thomas Hayden Church). Jack is on pre-wedding vacation with his best friend Miles (Paul Giamatti in one of his best roles), a wine aficionado and a talented writer. Although Miles connects with Stephanie on an intellectual level, as they both share a pretentious passion for wine, Jack’s interests are more romantic in nature. Jack hides his upcoming wedding from Stephanie, and they begin a passionate affair. Jack makes sure Miles stays quiet about the upcoming wedding; he is so focused on spending time with Stephanie that he neglects his responsibilities.

There is a sense of impending doom in Jack and Stephanie’s relationship. It is obvious that whatever happiness they temporarily found together is untenable. Jack is getting married soon, and he will be able to keep his secret for a very long time. However, even if Jack hasn’t been involved with another partner yet, Stephanie is too smart for him. She finds his curiosity and wry sense of humor charming, but it’s not exactly the basis for a relationship. O does a great job of showing how Stephanie judges Jack; she greets all his disgusting comments with a generous smile, as if she’s trying to stop herself from ridiculing him. Jack is so enamored with Stephanie that he doesn’t realize she might be laughing at him. Church and Oh do a great job of showing how differently the two characters view their relationship.. Jack imagines that Stephanie is the woman he has been looking for all his life, since she seems to share all of his interests. However, Stephanie does not see him as anything more than a passing fling. The specificity with which Oh portrays the character in such little screen time makes Sideways one of her most memorable performances.

Sandra Oh and Thomas Haden Church have great chemistry

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Spotlight pictures

Although Church has played more dramatic roles in the past, such as the Sandman in Spider-Man 3Jack is one of his most eccentric roles. The same can be said about O; Stephanie’s outgoing personality and outgoing sense of humor are no different from Eva Polastri. Their relationship works so well because it’s clear that both characters believe in a fantasy version of reality. A job consisting entirely of pouring wine seems like heaven to Jack. Although it’s just a job for Stephanie, Jack’s more fantastical ideas about their relationship allow her to temporarily accept how unique her profession is.

The relationship between Jack and Stephanie is even more fun compared to Miles. While Stephanie and Jack continued their romance, Miles gradually developed a relationship with Stephanie’s friend, Maya Randall (Virginia Madsen). Compared to Jack, Miles is clumsy, conflicted, and less romantic; Payne gets a hilarious and dark performance from Giamatti. The awkward interest Miles shows in Maya is the exact opposite of how attracted Jack and Stephanie are to each other. The exaggerated passion that Stephanie and Jack show for each other makes Miles feel even more isolated. In your limited capabilities O’s character was able to make Miles more convincing. as the main character.

Stephanie is one of Alexander Payne’s best female characters.

Although Sideways It was an early role in Oh’s career, meaning she could hold her own in the prestigious awards season alongside industry heavyweights like Giamatti and Church. Payne demonstrated an excellent ability to identify new talent and give them prominent roles; Stephanie is just one example of the future star’s stunning performance. Other notable female roles in Payne’s films include: Shailene Woodleyrole as George Clooneydaughter in Descendants, Laura Derncareer-defining role in Citizen RuthAnd Reese Witherspooncharacter Tracy Flick Electionswhich may very soon receive a sequel.

Stephanie is not necessarily one of the main roles in Sideways, but she has one of the most memorable scenes. As expected, Jack is unable to keep his engagement a secret, leaving Stephanie delighted. Her furious reaction brings Jack back to Earth as he realizes he has been playing with fire. It’s a critical scene that forces Jack and Miles to question their priorities. It was also a great showcase for Oh’s comedic talents, especially when the film started to veer towards more serious subject matter. O’s game is the epitome of the phrase, “No part is too small.” Simply because she has a smaller role in Sideways doesn’t mean it isn’t one of her most underrated performances to date.

Sideways Available to rent or buy on Apple TV+ in the US.