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Let’s Talk Cinema: The 2000s – Are You Not Entertained?

Jeremy Jentzen by Jeremy Jentzen
September 18, 2025
in featured, Jeremy Jentzen
33
Let’s Talk Cinema: The 2000s – Are You Not Entertained?

One of my many faults, much to my wife’s displeasure, is that I’m a night owl. For over a decade I worked third shift, which absolutely wrecked my sleep schedule. I’ve never been able to fully fix it. But in many ways, it shaped who I am today—because those long nights gave me plenty of time to watch movies. Now, when I crawl into bed and can’t get my brain to settle down, I slip into listing mode—which is partially how I ended up here, writing about our love of cinema and making goofy lists.

One of the ideas I had years ago was to take each decade and rewrite the Oscar winners—choosing who I would have wanted from the actual nominees. That idea sent me on a long journey to watch all the major Oscar winners. I still have about twenty films to go before I can say I’ve seen every Best Picture, Director, Actor, Actress, Supporting Actor, and Supporting Actress winners. Honestly, at this point, some of these movies need a rewatch or two. Some movies and performances have surprised me and aged beautifully, while others left me asking, “How and why did this win?!” Those questions are exactly what fuel my love for Oscar predictions and my yearly quest to see all the nominated films.

That brings me to this week’s assignment—one that might just turn into a series. I want to start with the year 2000, beginning with the Gladiator year and ending with the dreaded Hurt Locker year (2009). From each year’s nominees, choose who you would have crowned in Picture, Director, Actor, Actress, Supporting Actor, Supporting Actress, Adapted Screenplay, and Original Screenplay. Just for fun, let’s also throw in Animated Feature, since that category was introduced this decade. Of course, if you want to add other categories to your own list, go for it!

Jerm’s Official Rewrite of the Oscar Winners: The 2000s

2000
Picture – Gladiator
Director – Ridley Scott, Gladiator
Actor – Russell Crowe, Gladiator
Actress – Julia Roberts, Erin Brockovich
Supporting Actress – Kate Hudson, Almost Famous
Supporting Actor – Albert Finney, Erin Brockovich
Adapted Screenplay – O Brother, Where Art Thou?
Original Screenplay – Almost Famous

2001
Picture – The Lord of the Rings: The Fellowship of the Ring
Director – Peter Jackson, The Lord of the Rings: The Fellowship of the Ring
Actor – Russell Crowe, A Beautiful Mind
Actress – Halle Berry, Monster’s Ball
Supporting Actress – Helen Mirren, Gosford Park
Supporting Actor – Ethan Hawke, Training Day
Adapted Screenplay – The Lord of the Rings: The Fellowship of the Ring
Original Screenplay – Gosford Park
Animated – Shrek

2002
Picture – Chicago
Director – Roman Polanski, The Pianist
Actor – Adrien Brody, The Pianist
Actress – Renée Zellweger, Chicago
Supporting Actress – Catherine Zeta-Jones, Chicago
Supporting Actor – Chris Cooper, Adaptation
Adapted Screenplay – Adaptation
Original Screenplay – My Big Fat Greek Wedding
Animated – Spirit: Stallion of the Cimarron

2003
Picture – Mystic River
Director – Clint Eastwood, Mystic River
Actor – Sean Penn, Mystic River
Actress – Charlize Theron, Monster
Supporting Actress – Renée Zellweger, Cold Mountain
Supporting Actor – Tim Robbins, Mystic River
Adapted Screenplay – Mystic River
Original Screenplay – Finding Nemo
Animated – Finding Nemo

2004
Picture – Finding Neverland
Director – Martin Scorsese, The Aviator (terrible lineup to choose from)
Actor – Johnny Depp, Finding Neverland
Actress – Kate Winslet, Eternal Sunshine of the Spotless Mind
Supporting Actress – Cate Blanchett, The Aviator
Supporting Actor – Morgan Freeman, Million Dollar Baby
Adapted Screenplay – Finding Neverland
Original Screenplay – Eternal Sunshine of the Spotless Mind
Animated – The Incredibles

2005
Picture – Capote
Director – Bennett Miller, Capote
Actor – Philip Seymour Hoffman, Capote
Actress – Keira Knightley, Pride & Prejudice
Supporting Actress – Michelle Williams, Brokeback Mountain
Supporting Actor – Jake Gyllenhaal, Brokeback Mountain
Adapted Screenplay – Capote
Original Screenplay – The Squid and the Whale
Animated – Wallace & Gromit: The Curse of the Were-Rabbit

2006
Picture – The Departed
Director – Martin Scorsese, The Departed
Actor – Will Smith, The Pursuit of Happyness
Actress – Judi Dench, Notes on a Scandal
Supporting Actress – Cate Blanchett, Notes on a Scandal
Supporting Actor – Alan Arkin, Little Miss Sunshine
Adapted Screenplay – The Departed
Original Screenplay – Little Miss Sunshine
Animated – Cars

2007
Picture – No Country for Old Men
Director – The Coen Brothers, No Country for Old Men
Actor – Daniel Day-Lewis, There Will Be Blood
Actress – Marion Cotillard, La Vie en Rose
Supporting Actress – Cate Blanchett, I’m Not There
Supporting Actor – Javier Bardem, No Country for Old Men
Adapted Screenplay – No Country for Old Men
Original Screenplay – Lars and the Real Girl (I LOVE Juno and Ratatouille—tough choice!)
Animated – Ratatouille

2008
Picture – The Curious Case of Benjamin Button
Director – David Fincher, The Curious Case of Benjamin Button
Actor – Brad Pitt, The Curious Case of Benjamin Button
Actress – Meryl Streep, Doubt
Supporting Actress – Amy Adams, Doubt
Supporting Actor – Heath Ledger, The Dark Knight
Adapted Screenplay – The Curious Case of Benjamin Button
Original Screenplay – WALL-E
Animated – Kung Fu Panda

2009
Picture – Inglourious Basterds
Director – Quentin Tarantino, Inglourious Basterds
Actor – George Clooney, Up in the Air
Actress – Gabourey Sidibe, Precious
Supporting Actress – Mo’Nique, Precious
Supporting Actor – Christoph Waltz, Inglourious Basterds
Adapted Screenplay – Up in the Air
Original Screenplay – Inglourious Basterds
Animated – Up

Now, of course, I prefer my winners far more than what the Academy chose—but that’s the beauty of it. It’s all subjective. You might agree or disagree, and that’s okay. For me, the 2000s gave us some of my all-time favorites: Inglourious Basterds, No Country for Old Men, Little Miss Sunshine, The Departed, Chicago, Cold Mountain, The Curious Case of Benjamin Button, and Ratatouille. And legendary performances, like: Mo’Nique, Christoph Waltz, Heath Ledger, Javier Bardem, Marion Cotillard, and Queen Meryl—just so, so good.

I’d also love to hear your recommendations for hidden gems from the 2000s. What moved you? What inspired you? Drop them below—I’m always looking to discover something new.

The floor is yours now: rewrite your Oscars, stay within the nominees, have fun, and of course—Let’s Talk Cinema!

Tags: CapoteChicagoFinding NeverlandGladiatorInglourious BasterdsMystic RiverNo Country for Old MenThe Curious Case of Benjamin ButtonThe DepartedThe Lord of the Rings: The Fellowship of the Ring
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