The Rewatchables: Bill’s 50 Most Rewatchable Movies of the 21st Century

Host: Bill Simmons
Guests: Sean Fennessey, Chris Ryan
Date: December 30, 2025

Episode Overview

Bill Simmons, alongside Sean Fennessey and Chris Ryan, celebrates turning 50 by revealing his personal, painstakingly curated list of the 50 most rewatchable movies from the 21st century (2001–2025). The group goes through each pick, dissecting what makes a movie endlessly rewatchable, debating oversights, and riffing on personal favorites and family favorites. The episode is filled with signature Rewatchables banter, nostalgic storytelling, sharp industry analysis, and honest debates about taste and legacy.

Main Structure & Key Sections

1. Setup & Caveats

00:51–08:59

• Bill explains the genesis of his list and clarifies it’s a personal ranking (unapologetically subjective).
• Rules:
  • Only movies from 2001 onward; nothing from 2000 (so, no Cast Away, Almost Famous, Gladiator).
  • Family rewatchables (e.g., The Holiday, Love Actually) not counted if he’s not watching by choice.
  • No documentaries.
  • Doesn’t include movies his kids chose repeatedly (Mid90s, Big Time Adolescence).
  • Favored older movies over newer ones due to time with them.
  • Streaming-first releases only rarely included.
• Ongoing bit: Sean and Chris lob rapid-fire guesses and jokes about what the podcast episode will be about (“merch haul,” “Rewatchables blind,” “shooting a porn,” etc.).
• Quick caveats on how family taste and rewatching habits affect the list.

"Most important, they're just mine. This is my list."
— Bill Simmons (03:32)

2. Picks #50–41: Unexpected & Underdog Choices

10:20–22:40

• Bill dives right in, counting down from #50 to #41, explaining the unique “rewatchability” factor of each.
• Debate on singer-actor careers (e.g., Ashton Kutcher in A Lot Like Love), and why some unlikely movies hold up over time (Just Go With It, Flight, Equalizer).
• Strong focus on pure personal/family joy versus critical reputation.
• Sicario (#41) gets banter about Josh Brolin, Benicio Del Toro, Emily Blunt, and movie’s dark edges.

Notable Quotes:

• “I put a lot of thought into this. I made a list. I moved stuff around. I went crazy.” — Bill (03:22)
• “No 2000 movies, okay? Belong to the last century.” — Bill (04:16)
• “I just think [documentaries are] a different argument.” — Bill (05:51)

3. Picks #40–31: Comfort Watches & Canon Classics

23:42–39:16

• More mainstream entries start showing up: Collateral (#40), Mean Girls (#39), multiple Denzels (Man on Fire).
• Discussions touch on aging, geography, and family compatibility.
• Clear delight in banged-to-death comedies and “cable movie” phenomena.
• Top Gun: Maverick lands relatively low on the list because Bill feels he hasn’t had enough years to give it the true “endless rewatch” crown.

Notable Quotes:

• “If it's kidnapping, I'm there.” — Bill (09:17)
• “Every car also comes with a seven day money back guarantee…” — Sean (tongue-in-cheek, poking fun at an ad read) (23:14)

4. Picks #30–21: Personal Comforts & Modern Staples

39:16–58:13

• Garden State and Blackhat show Bill embracing movies with polarizing or dated reputations.
• Proof of Life triggers an extended, loving riff on Russell Crowe, Caruso, and the “hostage negotiator” melodrama.
• Frequent guest cross-examination about the mechanics of rewatchability (“Why didn’t you pick that?” “Is this Kutcher’s last appearance?”).
• A Star is Born and Get Out (2017) included as newer rewatchables already baked into Simmons household.
• Hardball and Moneyball reinforce Bill's sports-movie bias.
• Dark Knight discussion leads to lengthy Joker-vs-Bane riff.

Notable Quotes:

• “My favorite scene in Taken is when he shoots Jean Claude’s wife in the arm…” — Bill (75:34)
• “It's one of the rare movies on this list my wife, my daughter, and I all like equally.” — Bill on Mean Girls (26:32)
• “Sometimes they shoot their wad in the first five innings.” — Bill on Wedding Crashers (19:58)

5. Picks #20–11: Consensus “Classics” & Generational Markers

59:08–71:47

• Den of Thieves and No Country for Old Men represent pure adrenaline and pure craft.
• Bridesmaids and This Is The End spark conversations about the lost art of R-rated ensemble comedies.
• Limitless makes a shocking leap up the list—Bill admits he can’t explain his affection: “Do you. I can't tell you how many times I've watched this movie over the last 10 years.” (65:03)
• Old School, Fast Five, and Step Brothers round out a run that’s hilariously heavy on man-children, cool heists, and endless one-liners.
• “Comedy classic” is openly debated—does rewatchability favor comedy more than drama?

6. Picks #10–1: The Final Stretch & Top Rewatchables

71:47–88:34

#10–6:

• Step Brothers
• Taken
• Superbad
• The Hangover
• Miami Vice

Key insight: Comedies dominate the very top for honest personal/family reasons, while Miami Vice (a divisive, “midlife guy” cult classic) gets a passionate defense.

#5:

The Departed

• Universally beloved by the group (and listeners), with jokes about doing a “three-parted” episode.

#4:

The Town

• Outpaces Departed for Bill on the “Boston rewatch-o-meter” due to personal connections and endless cable play.

#3:

Anchorman

• An all-timer for the entire group; astonishing it hasn’t had an episode yet.
• “It’s the comedy I’ve seen rewatched, relived, cracked open the most times.”—Bill (83:49)

#2:

The Social Network

• “Perfect for a rewatchable standpoint. Jumping in anytime.”—Bill (85:03)
• Group discusses its growing modern relevance, upcoming sequel, and flawless execution.

#1:

The Devil Wears Prada

• Surprise—but, for Bill’s house, it’s “absolute rewatchables perfection.”
• “I think I've seen it the most times, and there's reasons for that, including my wife and my daughter. It's probably their favorite movie, but I always get sucked in.”—Bill (86:46)
• All agree it’s endlessly entertaining, cross-generational, and never lost its appeal.

“I think Devil Wears Prada will be on for this entire century. It's weirdly ageless. I don't see it, like, losing steam.” — Bill (88:05)

Memorable Quotes & Moments (with Timestamps)

• On Family Movie Dynamics:
  "There's sometimes when you're the offensive coordinator, but then the head coach says, I'm going to call the fourth quarter here. And that's—that's a whole genre of movies I didn't include."
  — Bill Simmons (05:14)

• Roasting Blackhat:
  “It’s an incoherent failure. I don’t know what else to say.”
  — Sean Fennessey (34:03)

• Limitless, Unfiltered:
  "Do you. I can't tell you how many times I've watched this movie over the last 10 years."
  — Bill Simmons (65:03)

• Anchorman’s power:
  "I laugh to a point where I feel like I'm hallucinating when I watch this movie."
  — Sean Fennessey (83:57)

• On The Devil Wears Prada:
  "Perfectly done. It's really well acted. Anne Hathaway and Blunt are fantastic in it. Streep. It's probably my favorite Meryl Streep performance... I think we achieve rewatchables perfection."
  — Bill Simmons (86:56–87:27)

Recurring Themes & Insights

• Rewatchability is deeply personal: Childhood nostalgia, where you live, and who you watch with shapes the list as much as cinematic quality.
• Family and spouse taste are critical: Bill repeatedly notes movies on the list as “all Simmonds family watches” or jokes about “offensive coordinating” for the living room.
• Comedies and “hangout” movies win: The flexibility to start watching midway, to join a movie in progress, or to dip in and out tips the scale heavily in favor of certain films.
• Adolescent-2000s movies loom large: The group laughs about how different a 1980s/1990s list would be but embraces the All-Time Cables of the 2000s-2010s.

Timestamps for Key Segments

• 00:51–08:59: Caveats and rules for Bill’s list
• 10:20–22:40: Movies #50–41
• 23:42–39:16: Movies #40–31
• 39:16–58:13: Movies #30–21
• 59:08–71:47: Movies #20–11
• 71:47–88:34: Movies #10–1 and final discussion

Final Reflections & Wrap-Up

The episode wraps with the group reflecting on how these lists shift over time, how family and living arrangements tweak one’s private canon, and how certain surprise picks like Devil Wears Prada or Blackhat become touchstones. The absence of Zodiac is lamented (“Zodiac was supposed to be on this. I knew I was going to make a mistake.” — Bill (94:34)), and there’s a gleeful promise to revisit missed movies and possibly revisit their entire approach to “rewatchability.”

"There's no way to do it perfectly... but I tried." — Bill Simmons (95:29)

For New Listeners

This episode is a love letter to the movies that fill in the corners of our lives—sometimes the “greatest,” often the most comforting, occasionally the ones we never expected to enjoy so much. As always, The Rewatchables crew leans into deep dives, playful debates, and pure movie enthusiasm. Whether you agree with every pick or not, you’ll come away with a rich sense of how movies shape memories and foster family lore.