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Dispatches from Home: The top films of the last 20 years

A starter's guide to catching up on the best Hollywood has had to offer in the 21st century. Here's one man's list of what to watch.

A stock photo that manages to include three movies I’ve seen in the last 20 years … but none that make my personal Top 20 list.

We’re now in our third month of isolation. 

You’ve run out of ways to entertain yourself and your family. You’ve played Monopoly so many times you don’t even need to move the little Scottish Terrier space-to-space with each roll of the dice because you know the board by heart. You’ve overdosed on Facebook and have watched the entirety of Netflix.

How about hosting your own Very Special Coronavirus Pandemic Film Fest? Movies are fun and time consuming, and at least prior to the great television revolution of the last two decades, my primary form of in-home entertainment. 

If I was tasked with putting together a list of my all-time favorite films, the selections, as with anyone’s, would skew toward movies I grew up with as a child and teen. To make this a bit more challenging, I’m going to present to you, loyal reader, the 20* very best** films of the last 20 years, which coincides with my 20 years of adulthood, having graduated college 20 years ago next month.

*There are no refunds if you happen to count more than 20.

**By “very best,” the author simply means favorites of his; this is a very subjective exercise. 

Two rules: I couldn’t repeat any single director (so, only one David Fincher and one Quentin Tarantino film allowed) and the film had to be released no earlier than 2000. (And a rule that probably doesn’t need to be stated: I had to have seen it. My shame list, sadly, is a little long: Here’s looking at you, “The Wolf of Wall Street.”)

This list is verified fresh by my fiance, who looked at my work via pencil and notepad paper (not one erase mark!) and volunteered, “This is a good list.”

Almost Famous. Probably the reason I made this list and easily one of my all-time favorites. Kate Hudson’s Penny Lane is charming and the supporting cast is incendiary. 

Anchorman: The Legend of Ron Burgundy. When I set out to make this list, I was only going to include one comedy. It wasn’t this one. So of course that rule went out the window. I dare you to find a more quotable movie from the last 20 years.

Best in Show. This mockumentary has both dogs and silly humor, two of my favorite things. Fred Willard (dim-witted sports TV analyst) and Parker Posey (crazed and obsessive dog show mom) are perfect.

The Bourne Identity. “Die Hard” set the standard for action movies more than 30 years ago. (I feel old typing those last three words). “Bourne” ushered the genre into the 21st century with Doug Liman’s frenetic, hang-onto-your-hat tale of a hitman recovering from amnesia.

The Dark Knight. Nearly finished this list without one superhero movie (the genre that’s clearly taken over the world lately) but I look at this as more of a villain movie anyway. The opening scene, when we meet Heath Ledger’s Joker during a bank robbery, is reminiscent of “Heat.” 

The Departed. Sure Martin Scorsese deserved an Oscar long before this (“Goodfellas,” for one) but that shouldn’t take away from how enjoyable this remake of China’s “Internal Affairs” is with a killer ensemble cast. 

Eternal Sunshine of the Spotless Mind. Writer Charlie Kaufman had a heck of a five-year run, with this, “Adaptation” and “Being John Malkovich.” But this is my favorite: Who doesn’t like Jim Carrey in a drama or hasn’t thought about what it would be like to erase your memory after a tough breakup?

Get Out. It felt wrong to have a list without at least one horror entrant. Horror only works for me if it feels realistic and leaves you feeling unsettled throughout and Jordan Peele’s directorial debut goes 2-for-2. 

Gone Baby Gone. Another directorial debut, this one from Ben Affleck, and another movie that made me want to make this list. If you haven’t read any of Dennis Lehane’s crime novels with detectives Patrick Kenzie and Angie Gennaro, start with this movie that twists and turns and leaves you debating with your friends and family about whether they did the right thing afterward. 

Inglourious Basterds. Did I want to initially include “Once Upon a Time in Hollywood?” Yes, but I feel like Quentin Tarantino’s “Basterds” made “Hollywood” possible. It’s arguably his best and the very best film since 2000, period.

A small sampling of my personal, eclectic film library. (RYAN LAWRENCE/The Sun)

JoJo Rabbit. How do you take a serious subject and produce a film that’s charming, witty, silly, and moving? Taiki Waititi, the writer, director and actor who plays Hitler unlike anyone else before, nails it in the best film of 2019.

Love Actually. It’s been added to “It’s a Wonderful Life” and “A Charlie Brown Christmas” on my must-watch holiday season list. That’s high praise.

Mean Girls. So I’m going to answer my own question from earlier and say that this might be the most quoted movie of the last 20 years, among people of a certain age, of course. Also: easily the best high school comedy of the last 30 years.

Miracle. I suggest a new tradition for you and yours: Instead of watching those tired fireworks shows, put this on every July 4 after you’re grilling hamburgers and hot dogs. 

Moneyball. I usually like Brad Pitt in the supporting roles (“Fight Club,” “12 Monkeys” and, of course, “True Romance”), but he’s pretty great here in the lead of a movie with real heart despite being based on the beginning of the analytical revolution in baseball. 

Seabiscuit. This true story isn’t centered around the horse in title but on the three men who overcome their own failures in the best sports movie of the last 20 years.

Silver Linings Playbook. If this list was only five films long, this, the story of a super-Eagles fan adjusting to life with his family after a stint in a medical institution, would be on there. Perfectly cast.

The Social Network. I could have chosen a few different Fincher films — it’s a crime the director and the two leads didn’t get to the other two-thirds of the trilogy after “The Girl with the Dragon Tattoo” — but this one seems to have the most staying power and continues to feel relevant as Facebook continues to influence society. 

Wall-E. “Wall-E” isn’t just here so an animated film is represented, it’s here because it’s moving, original, inventive, thought-provoking and a fun watch, too.

The 40-year-old Virgin. The funniest film in the last 25 years, Steve Carell and Judd Apatow’s troupe are at the height of their comedic powers. 

(500) Days of Summer. How is this for a curveball: a romantic comedy told through the perspective of a man.

You’ve gotten this far so here is your reward: five honorable mentions, by genre. Action/Adventure: “Pirates of the Caribbean.” Animated: “Up.” International: “City of God” (This should have probably made the list up top, but I simply haven’t seen it in about 18 years). Drama: “The Discovery.” Indie: “A Ghost Story.”

So that’s my 20 … 21 … er, 26. 

Since you probably won’t be turned off by even more recommendations for your Very Special Coronavirus Pandemic Film Fest, my cousin Patrick, who just celebrated a milestone birthday last week (happy birthday!) and whose film buff status puts me to shame regularly, followed the same rules and submitted his own top 20 since 2000: 

“No Country for Old Man,” “There Will Be Blood,” “The Wolf of Wall Street,” “Steve Jobs,” Adaptation,” “City of God,” “Zodiac,” “Borat: Cultural Learnings of America for Make Benefit Glorious Nation of Kazakhstan,” 24 Hour Party People,” “You Were Never Really Here,” “The Incredibles,” “Anchorman: The Legend of Ron Burgundy,” “Hedwig and The Angry Inch,” “Donnie Darko,” “Once Upon a Time in Hollywood…,” “Pan’s Labyrinth,” “Into the Wild,” “The Prestige,” “The Place Beyond the Pines,” and “Hereditary.” 

Get your popcorn ready and happy viewing.


Dispatches from Home is a new weekly feature from Sun Newspapers. The smart and safe coronavirus epidemic isolations have surely left us all a little stir crazy. Each week, Ryan Lawrence will offer some ideas to keep you busy, entertained — or both.

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