Home/Episodes/Bill’s 50 Most Rewatchable Movies of the 21st Century | With Sean Fennessey and Chris Ryan
Bill’s 50 Most Rewatchable Movies of the 21st Century | With Sean Fennessey and Chris Ryan
December 30, 2025 · 1:37:21 · ▶ Listen on Spotify
Bill's 50 Most Rewatchable Movies of the 21st Century
Ranked list · Bill Simmons · ▶ 10:25
- 50Just Go with It (2011)▶ 10:25
- 49A Lot Like Love (2005)▶ 11:52
- 48Knocked Up (2007)▶ 14:37
- 47Flight (2012)▶ 15:39
- 46The Equalizer (2014)▶ 17:18
- 45Miracle (2004)▶ 18:39
- 44Borat (2006)▶ 19:01
- 43Wedding Crashers (2005)▶ 19:37
- 42The Wolf of Wall Street (2013)▶ 21:19
- 41Sicario (2015)▶ 21:39
- 40Collateral (2004)▶ 23:49
- 39Mean Girls (2004)▶ 25:41
- 38Man on Fire (2004)▶ 26:49
- 37Top Gun: Maverick (2022)▶ 28:02
- 36Lost in Translation (2003)▶ 30:06
- 35Garden State (2004)▶ 31:56
- 34Blackhat (2015)▶ 33:27
- 33Proof of Life (2000)▶ 34:30
- 32A Star Is Born (2018)▶ 37:45
- 31Funny People (2009)▶ 39:25
- 30Get Out (2017)▶ 42:27
- 29Hardball (2001)▶ 43:59
- 28Moneyball (2011)▶ 45:47
- 27The Dark Knight (2008)▶ 47:05
- 26Ocean's Eleven (2001)▶ 49:23
- 25Creed (2015)▶ 51:39
- 24Furious 7 (2015)▶ 52:53
- 23John Wick: Chapter 2 (2017)▶ 55:42
- 22Gone Girl (2014)▶ 56:42
- 21Forgetting Sarah Marshall (2008)▶ 57:43
- 20Den of Thieves (2018)▶ 1:00:08
- 19No Country for Old Men (2007)▶ 1:01:28
- 18Bridesmaids (2011)▶ 1:03:26
- 17This Is the End (2013)▶ 1:04:34
- 16Limitless (2011)▶ 1:05:31
- 15Sideways (2004)▶ 1:08:12
- 14Spotlight (2015)▶ 1:09:02
- 13Before Sunset (2004)▶ 1:10:24
- 12Old School (2003)▶ 1:11:31
- 11Fast Five (2011)▶ 1:12:34
- 10Step Brothers (2008)▶ 1:13:46
- 9Taken (2008)▶ 1:14:45
- 8Superbad (2007)▶ 1:17:23
- 7The Hangover (2009)▶ 1:17:49
- 6Miami Vice (2006)▶ 1:18:56
- 5The Departed (2006)▶ 1:21:46
- 4The Town (2010)▶ 1:22:32
- 3Anchorman (2004)▶ 1:24:20
- 2The Social Network (2010)▶ 1:25:44
- 1The Devil Wears Prada (2006)▶ 1:27:26
Sean's most-rewatched movies of the 21st century
Unranked list · Sean Fennessey · ▶ 1:29:54
- ·There Will Be Blood (2007)▶ 1:29:54
- ·Inglourious Basterds (2009)▶ 1:35:02
- ·The Wolf of Wall Street (2013)▶ 1:35:04
- ·The Departed (2006)▶ 1:35:05
- ·Zodiac (2007)▶ 1:35:11
Chris's most-rewatched movies of the 21st century
Unranked list · Chris Ryan · ▶ 1:30:36
- ·Miami Vice (2006)▶ 1:30:36
- ·Sicario (2015)▶ 1:30:39
- ·Inglourious Basterds (2009)▶ 1:30:43
- ·Scream (1996)▶ 1:31:51
- ·The Nice Guys (2016)▶ 1:35:34
Chapters
Movies Referenced (101)
13 mentions · Bill Simmons, Sean Fennessey, Chris Ryan▶ 1:35:08IMDb ↗Lb ↗
7 mentions · Chris Ryan, Bill Simmons, Sean Fennessey▶ 25:12IMDb ↗Lb ↗
7 mentions · Sean Fennessey, Bill Simmons, Chris Ryan▶ 34:31IMDb ↗Lb ↗
5 mentions · Bill Simmons, Chris Ryan, Sean Fennessey▶ 23:50IMDb ↗Lb ↗
5 mentions · Chris Ryan, Sean Fennessey, Bill Simmons▶ 18:09IMDb ↗Lb ↗
5 mentions · Bill Simmons, Sean Fennessey, Chris Ryan▶ 55:44IMDb ↗Lb ↗
4 mentions · Chris Ryan, Sean Fennessey, Bill Simmons▶ 1:25:02IMDb ↗Lb ↗
Directors Referenced (12)
4 mentions · Sean Fennessey, Chris Ryan · Known for Almost Famous, Jerry Maguire, Vanilla Sky▶ 2:26IMDb ↗Lb ↗
4 mentions · Sean Fennessey, Bill Simmons, Chris Ryan · Known for The Martian, Blade Runner, Thelma & Louise▶ 1:34:21IMDb ↗Lb ↗
4 mentions · Chris Ryan, Sean Fennessey · Known for Ray, Blood In, Blood Out, Dolores Claiborne▶ 35:33IMDb ↗Lb ↗
3 mentions · Sean Fennessey, Bill Simmons · Known for The Insider, Collateral, The Last of the Mohicans▶ 24:10IMDb ↗Lb ↗
3 mentions · Chris Ryan, Bill Simmons · Known for Domino, Unstoppable, True Romance▶ 27:05IMDb ↗Lb ↗
1 mentions · Sean Fennessey · Known for The Saint, Open Your Eyes▶ 1:09:42IMDb ↗Lb ↗
1 mentions · Sean Fennessey · Known for Serial Mom, Thirteen Days▶ 36:21IMDb ↗Lb ↗
1 mentions · Sean Fennessey · Known for Dune: Part One, Dune: Part Two, Blade Runner 2049▶ 21:58IMDb ↗Lb ↗
1 mentions · Sean Fennessey · Known for Up in the Air, Ghostbusters▶ 14:06IMDb ↗Lb ↗
1 mentions · Sean Fennessey · Known for Planes, Trains & Automobiles, Uncle Buck, The Breakfast Club▶ 26:23IMDb ↗Lb ↗
1 mentions · Sean Fennessey · Known for Dances with Wolves, Robin Hood: Prince of Thieves▶ 13:36IMDb ↗Lb ↗
Actors Referenced (95)
8 mentions · Sean Fennessey, Bill Simmons, Chris Ryan · Known for 2012, A Lot Like Love, The Whole Nine Yards▶ 11:52IMDb ↗Lb ↗
7 mentions · Bill Simmons, Chris Ryan, Sean Fennessey · Known for A Lot Like Love▶ 11:52IMDb ↗Lb ↗
6 mentions · Bill Simmons, Sean Fennessey, Chris Ryan · Known for Lost in Translation, Rushmore, Moonrise Kingdom▶ 30:12IMDb ↗Lb ↗
6 mentions · Sean Fennessey, Bill Simmons, Chris Ryan · Known for Just Go with It, Battleship, What to Expect When You're Expecting▶ 11:03IMDb ↗Lb ↗
5 mentions · Bill Simmons, Sean Fennessey, Chris Ryan · Known for A Star Is Born, Silver Linings Playbook, American Sniper▶ 20:18IMDb ↗Lb ↗
4 mentions · Bill Simmons, Sean Fennessey · Known for Schindler's List, The Grey▶ 1:15:26IMDb ↗Lb ↗
4 mentions · Bill Simmons, Chris Ryan · Known for Garden State▶ 32:24IMDb ↗Lb ↗
3 mentions · Bill Simmons, Sean Fennessey · Known for Drive, Broadcast News, Defending Your Life▶ 23:12IMDb ↗Lb ↗
3 mentions · Chris Ryan, Bill Simmons, Sean Fennessey · Known for The Lobster, In Bruges, S.W.A.T.▶ 31:44IMDb ↗Lb ↗
3 mentions · Sean Fennessey, Bill Simmons · Known for Edge of Tomorrow, The Devil Wears Prada, The Adjustment Bureau▶ 22:15IMDb ↗Lb ↗
3 mentions · Bill Simmons · Known for We're the Millers▶ 10:32IMDb ↗Lb ↗
Writers Referenced (4)
5 mentions · Bill Simmons, Sean Fennessey · Known for The King of Staten Island, Knocked Up▶ 15:04IMDb ↗Lb ↗
1 mentions · Bill Simmons · Known for The Road, No Country for Old Men, The Counselor▶ 1:03:18IMDb ↗Lb ↗
1 mentions · Bill Simmons · Known for It's Complicated, Something's Gotta Give, Private Benjamin▶ 4:56IMDb ↗Lb ↗
1 mentions · Chris Ryan · Known for Michael Clayton, Rogue One: A Star Wars Story▶ 35:33IMDb ↗Lb ↗
Cinematographers Referenced (1)
1 mentions · Bill Simmons · Known for War for the Planet of the Apes, Logan, Terminator Genisys▶ 27:21IMDb ↗Lb ↗