In the years since "Sideways," Paul Giamatti has solidified his position as a leading man in the entertainment industry. Known for his ability to carry a movie, whether it be indie gems like “Private Life” and “Win Win” or acclaimed series like “John Adams” and "Billions," Giamatti has proven his versatility as an actor. However, despite his extensive career, “Sideways” remains a significant milestone for him. Giamatti fondly recalls his experience making the film, staying in a little house in the middle of a large vineyard in Napa Valley. It was one of his first times as a lead actor, and he couldn't believe the opportunity he had been given.

Now, two decades later, Giamatti finds himself reteaming with director Alexander Payne for "The Holdovers." The film, playing in theaters and available digitally, showcases the same alchemy between Giamatti and Payne that made “Sideways” so successful. Although the setting has shifted from California sunshine to snowy New England, and from wine to whisky, there is a faint connection between the two movies. Giamatti plays Paul Hunham, an irascible classics professor at a 1970s boarding school who is widely disliked by his students. Forced to spend Christmas break with a handful of students, the movie evolves from a broad comedy to a tender humanistic drama centered around Hunham, a bright but less privileged student, and the school's grieving head cook.

For Giamatti, “The Holdovers” prompts reflection on the distance he has traveled in the intervening decades. He acknowledges the significant life changes and professional growth he has experienced since "Sideways," including divorce and various career opportunities. Giamatti finds similarities between the characters of Miles Raymond in “Sideways” and Hunham in "The Holdovers." Both are prickly misanthropes stuck in a midlife stasis, but Giamatti finds himself drawn to Hunham's character, who he believes has more zest and enjoys being the “a-hole” that he is.

The collaboration between Giamatti and Payne has been long-awaited. They have discussed potential projects over the years, including a private-eye film and a Western. However, it wasn't until Payne met screenwriter David Hemingson and had the idea to loosely adapt the 1935 French comedy “Merlusse” that they found the right project. Payne speaks highly of Giamatti, describing him as the best and finest actor who can do anything. Giamatti appreciates the trust Payne has in him and their ability to work together, citing a scene from “Sideways” as an example of their collaboration.

While working on "The Holdovers," Giamatti and Payne had their first disagreement during a scene when Paul is in a tense meeting with the parents of a student. Giamatti initially decided to sit down, believing it showed Paul breaking protocol. However, after discussing it with Payne, they both came around to each other's ideas, and Giamatti ultimately preferred standing. This disagreement highlights the strong working relationship between Giamatti and Payne.

Due to the actors' strike, Giamatti and his castmates, including Da'Vine Joy Randolph and Dominic Sessa, were unable to promote "The Holdovers." However, Giamatti found himself frustrated by not being able to talk about the film because he genuinely wanted to share his enthusiasm for it. Although he is not counting on receiving an Oscar nomination, many predict that Giamatti may finally receive his first Academy Award nomination for his role in "The Holdovers."

If Giamatti is nominated, it would be a long-overdue acknowledgement of his talents as one of the finest actors of this era. His ability to bring wit and warmth to everyman characters has made him a standout performer. Despite his down-to-earth demeanor, Giamatti's fascination with topics like Sasquatch, UFOs, and ghosts showcases his penchant for the weird and unconventional. Through his podcast, Chinwag, Giamatti is finally able to explore these interests openly.

“The Holdovers” marks a significant milestone in the careers of Paul Giamatti and Alexander Payne. Their reunion after 20 years since “Sideways” has resulted in another powerful collaboration that showcases Giamatti's exceptional acting abilities. As Giamatti reflects on his journey and the connection between the two films, he acknowledges the impact and significance of both “Sideways” and “The Holdovers” in his career.