Bill’s 50 Most Rewatchable Movies of the 21st Century | With Sean Fennessey and Chris Ryan

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.

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.