Key Takeaways
- Bill Simmons unveiled his personal list of the 50 most rewatchable films of the 21st century.
- The list excluded movies from the year 2000 and those primarily chosen by family members.
- Methodology emphasized personal recall and shared viewing preferences over strict metrics.
- Newer films and streaming-first releases presented challenges for inclusion on the list.
- "The Devil Wears Prada" was ranked number one, followed by "The Social Network" at number two.
Deep Dive
- Bill Simmons' list details the 50 most rewatchable movies of the 21st century, explicitly excluding films from the year 2000.
- The selection is a personal one, omitting movies primarily watched due to his wife's preference, such as "The Holiday" and "Love Actually."
- Documentaries and films predominantly chosen by his son, including "Mid 90s" and "Big Time Adolescence," were also not included.
- A host noted difficulty in including newer films and streaming-first releases, with a tendency to favor movies from 2001-2010.
- The list's methodology relies on mental recall, ownership, and shared viewing preferences rather than strict metrics.
- "Flight" (ranked 47th) is noted for Denzel Washington's NTSB hearing scenes and a memorable plane crash sequence.
- "The Equalizer" (ranked 46th) is described as a "textbook rewatchable," with its consistent quality compared to the "Taken" series.
- "Miracle" (2004) is 45th, praised for its speeches and depiction of the US beating Russia in hockey.
- "Borat" (44th) is lauded for its humor despite being nearly 20 years old; "Wedding Crashers" (43rd) is noted for its strong first hour.
- "Wolf of Wall Street" (42nd) is highlighted for fast pacing; "Sicario" (41st), a Denis Villeneuve film, features Josh Brolin and Emily Blunt.
- "Collateral" (40th), a Michael Mann film from 2004-2005, is cited for its surprising rewatchability, accurate LA setting, and Tom Cruise's performance.
- "Mean Girls" (39th) is highlighted as a funny family movie that has aged well, praised for its smart writing and cast including Lindsay Lohan and Tina Fey.
- "Man on Fire" (38th) is considered a favorite Denzel Washington performance by one speaker, also noting Dakota Fanning's role and Tony Scott's stylish direction.
- "Top Gun: Maverick" (37th) is seen as a major cinematic event and one of the most-seen movies of the decade, yet its lower ranking surprised hosts.
- "Blackhat" (ranked 34th) is a complex Michael Mann film involving a nuclear reactor and global locations; one host admits to rewatching it with commercials.
- "Proof of Life" (33rd), starring Russell Crowe and Meg Ryan, sparks debate about its quality and whether it was overlooked.
- "A Star is Born" (the Bradley Cooper version) is ranked 32nd and described as a quality film and a favorite within Bill Simmons' household.
- Lady Gaga's performance in "A Star is Born" is praised, along with a specific bar scene featuring an Almond Brothers song.
- The rewatchability of Jordan Peele's "Get Out" is discussed, with a host preferring his later works, "Us" and "Nope," for their depth.
- A general preference for rewatching older horror films like "The Omen" over newer ones is noted.
- "Any Given Sunday" is debated for its relevance and prescient themes, considered for a future "Rewatchables" episode.
- "Moneyball" (ranked 28th) is highlighted for its broad appeal across different moviegoers and significant cultural impact.
- "Creed" (ranked 25th) is lauded as a modern classic and a perfect sports movie.
- "Fast and Furious 7" (24th) is noted for its emotional ending following Paul Walker's death and the film's production challenges.
- "John Wick 2" (23rd) surprisingly ranked lower than expected, praised for its action sequences, while "John Wick 1" was omitted.
- The hosts evaluate "John Wick" sequels, calling "four" a borderline masterpiece and "two" a home run.
- "Den of Thieves" (ranked 20th) is considered a solid action movie, with performances by Pablo Schreiber and 50 Cent noted.
- "No Country for Old Men" (19th) is praised for its timeless quality; a host's appreciation shifted over the past decade, especially for its ending.
- "Bridesmaids" (18th) is identified as a major comedy hit and a family favorite, lamenting the decline of R-rated comedies.
- The supporting cast of "Bridesmaids," including Maya Rudolph and Rose Byrne, is highlighted as one of the best in recent years, noting Melissa McCarthy's emergence.
- "Spotlight" (ranked 14th) is acknowledged as a controversial but rewatchable "process movie," drawing parallels to "All the President's Men."
- "Before Sunset" (13th) has been covered extensively, while "Before Midnight" is noted as a "rough" but interesting exploration of marriage.
- "Old School" (12th) is a "Simmons fam" staple, praised for its rewatchability, humor, and Luke Wilson's performance.
- "Fast Five" (11th) is called an "unbelievable achievement" and the peak of the franchise, featuring numerous set pieces in Brazil and one of the best action movie endings.
- "Miami Vice" (2006) is appreciated for its aesthetic, Colin Farrell's performance, and its continuous sense of motion from beginning to end.
- "The Departed" is praised as a mid-2000s reinvention and a prime example of a rewatchable film.
- A debate arises about whether Jack Nicholson's performance in "The Departed" was his last truly great role.
- One participant ranks "The Town" higher than "The Departed" due to its Boston setting and personal rewatchability.
- "The Devil Wears Prada" is crowned the number one most rewatchable film, cited for its high rewatch frequency and Meryl Streep's performance.
- "The Social Network" is number two, praised for its increasing relevance and strong cast, including Jeremy Strong and Mikey Madison.
- "Anchorman" is number three, highlighted for its comedic value, though its long-term appeal for younger audiences is debated.
- The top two films, "The Devil Wears Prada" and "The Social Network," are both slated for sequels in 2026, prompting discussion on their "ageless" rewatchability.