Paul Giamatti in the context of "Billions (TV series)"

Sideways is a 2004 American comedy-drama directed by Alexander Payne and written by Jim Taylor and Payne. A film adaptation of Rex Pickett's 2004 novel, Sideways follows two men in their forties, Miles Raymond (Paul Giamatti), a depressed teacher and unsuccessful writer, and Jack Cole (Thomas Haden Church), a past-his-prime actor, who take a week-long road trip to Santa Barbara County wine country to celebrate Jack's upcoming wedding. Sandra Oh and Virginia Madsen also star as women they encounter during their trip.

Sideways premiered at the Toronto International Film Festival on September 13, 2004, and was released in the United States on October 22, 2004. It received widespread acclaim from critics and is regarded as one of the greatest films of the 2000s. At the 77th Academy Awards, the film was nominated for Best Picture, Best Director, Best Supporting Actor (Haden Church), Best Supporting Actress (Madsen), and Best Adapted Screenplay, the last of which it won.

The Truman Show is a 1998 American comedy-drama film written and co-produced by Andrew Niccol, and directed by Peter Weir. The film depicts the story of Truman Burbank (played by Jim Carrey), a man who is unaware that he is living his entire life on a colossal soundstage, and that it is being filmed and broadcast as a reality television show that has a huge international following. All of his friends, family, and members of his community are paid actors whose job is to sustain the illusion and keep Truman unaware of the false world he inhabits. The film's supporting cast includes Laura Linney, Ed Harris, Noah Emmerich, Natascha McElhone, Holland Taylor, Paul Giamatti, and Brian Delate.

Niccol's original spec script was more of a science-fiction thriller, with the story set in New York City. Producer Scott Rudin purchased the script and set up production at Paramount Pictures. Brian De Palma was to direct before Weir signed on as director, making the film for $60 million—$20 million less than the original estimate. Niccol rewrote the script while the crew was waiting for Carrey to sign. The majority of filming took place at Seaside, Florida, a master-planned community located in the Florida Panhandle.

The Illusionist is a 2006 American romantic mystery film written and directed by Neil Burger and starring Edward Norton, Paul Giamatti, and Jessica Biel. Based loosely on Steven Millhauser's short story "Eisenheim the Illusionist", it tells the story of Eisenheim, a magician in turn-of-the-century Vienna, who reunites with his childhood love, a woman far above his social standing. It also depicts a fictionalized version of the Mayerling incident.

It premiered at the 2006 Sundance Film Festival and opened the 2006 Seattle International Film Festival; it was distributed in limited release to theaters on August 18, 2006 and expanded nationwide on September 1. It was a critical and commercial success.