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It was easy to laugh when you went to the movies last decade. There were several brilliant new comedy minds starting to make movies around the early 2000s, which led to a decade of classic or soon-to-be classic comedies.
Will Ferrell and writer-director Adam McKay emerged from their time at Saturday Night Live to create three of the funniest movies in recent history (Anchorman, Talladega Nights, and Step Brothers). Judd Apatow moved from TV in the late 90s (Freaks and Geeks, Undeclared) to the big screen, where he made comedy stars out of Steve Carell (The 40-Year-Old Virgin) and Seth Rogen (Knocked Up). Vince Vaughn, Owen Wilson, Ben Stiller, Tina Fey, Paul Rudd, Amy Poehler, and more were delivering endless laughs. And I haven’t even alluded to School of Rock, Borat, or one of the most successful R-rated movies of all-time, The Hangover, which capped the decade in riotous fashion.
Fortunately, many of these are streaming right now, so let’s talk about four of our personal favorite laugh-until-you-cry 2000s comedies.
Drew recommends…
Pineapple Express (streaming on Netflix)
I was in high school when Pineapple Express came out, so you can imagine how amped we were once we saw the uproarious trailer, which featured the perfect music cue in M.I.A.’s “Paper Planes.” Ten-plus years later, of all the Judd Apatow-universe 2000s comedies, Pineapple Express remains the one I return to most often.
Written by Seth Rogen and his writing partner Evan Goldberg, this 2008 stoner flick has action shootouts, buddy comedy, and pot jokes for days. It also has some riotous performances from its hilarious cast. Back in 2008, James Franco hadn’t really shown his funny side, but Pineapple Express would pave the way for his comedy work in films like This Is the End and The Disaster Artist. As Saul Silver, the oblivious weed dealer caught up in murder and corruption, Franco surprised by revealing he had real comedy chops, in addition to his dramatic work. This was also an early Danny McBride performance -- I remember being shocked I had never seen this hilarious person in anything before.
I’ve seen this so many times that the best scenes and lines come back to me instantly: Franco driving the police cruiser with his foot through the red slushie-covered front windshield; McBride carrying a shotgun while wearing a neckbrace (“Thug life”); Franco rambling about his “second-favorite civil engineer.” The whole movie feels loose and fun without leaning too heavily on improv. Pineapple Express has to be one of the great lazy afternoon movies of this century.
Talladega Nights: The Ballad of Ricky Bobby (streaming on Amazon Prime)
It’s either this or Dodgeball for best sports comedy of the 2000s. These two incredibly stupid yet undeniably hysterical movies never fail to make me cackle with sheer delight. In Talladega Nights, everyone is so fully committed to their ridiculous characters that just about everything works. Will Ferrell’s loudmouth NASCAR driver Ricky Bobby trails only Ron Burgundy when ranking Ferrell’s ignorant-and-proud idiot characters.
(Let’s just pause for a moment to appreciate Will Ferrell from 2003 to 2008, shall we? Every single year in that stretch he had at least one hit. Old School and Elf in 2003, Anchorman in 2004, Wedding Crashers in 2005, Talladega Nights in 2006, Blades of Glory in 2007, and Step Brothers in 2008. What a legendary comedy run.)
Ricky Bobby’s racing partner (and half of the “Shake ‘n Bake” duo) Cal Naughton Jr. is played with splendid lunacy by the great John C. Reilly. Talladega Nights doesn’t work half as well as it does if Reilly isn’t there. His barely concealed dissatisfaction with always giving up first place for Ricky makes the movie fire on all cylinders when French Formula One driver Jean Girard (Sacha Baron Cohen) causes discord between Cal and Ricky. Ricky’s downfall then becomes perhaps the funniest part of the movie.
Much like Anchorman, Talladega Nights has an all-star supporting cast. Baron Cohen, Amy Adams, and Leslie Bibb (as Carley, Ricky’s shallow trophy wife) are allowed to get weird and wild with their characters. In smaller parts, Jane Lynch, Molly Shannon, and Andy Richter steal their scenes. And who can forget Ricky’s sons Walker and Texas Ranger, who mercilessly terrorize their grandpa Chip. Co-writers Ferrell and Adam McKay give every actor a juicy comedic role.
As with just about every Ferrell and McKay movie, Talladega Nights is wildly quotable: “If you ain’t first, you’re last.” “Help me Tom Cruise!” “Don’t you put that evil on me, Ricky Bobby!” “Chip, I’m all jacked up on Mountain Dew!” I could keep going for awhile, but in the interest of space I limited myself to those four.
Ferrell and McKay tried to hit on this sports satire formula two more times during the decade, with Blades of Glory and Semi-Pro, but those mostly failed to reach the same comedic heights and didn’t have a co-star as skilled as John C. Reilly. Talladega Nights simply has that perfect balance of improvisational silliness and plot-driven insanity. Thank newborn infant baby Jesus that they made this ludicrous movie.
Billy recommends…
Mean Girls (streaming on HBO Now)
Looking back on this movie is such a strange trip. At the time it was an unexpected hit, but upon rewatching it is so obvious why this movie is turning into a classic. First of all we have an unexpected all-star cast with Rachel McAdams playing an all-time villain.
It is not often such an iconic villain comes from a comedy. Regina George is a mixture of a person you completely hate, but also has such a magnetism to her. Coincidentally, it is played by one of our most talented actresses, Rachel McAdams. That is why this movie is so much fun on a rewatch. Almost every actress has turned out to be a leading lady at one point. The obvious is Lindsay Lohan who was on the path to being an all-time star. Plus we had plenty of actresses like Amanda Seyfriend, Rachel McAdams, Tina Fey, Amy Poehler, and Lizzy Caplan, who have all had their time to shine. And what is the one common theme between all of them? They are unbelievably funny.
Tina Fey, the screenwriter of this movie, wrote these characters beautifully. There is no weak link. Consistency is such a hard thing to obtain in any movie and not many movies are as consistent as Mean Girls. The villain is great, the lead is great, and the supporting characters make the leads even stronger. Mean Girls is a near-perfect comedy that is great for any audience. This one might be worth a free trial run of HBO Now.
Superbad (streaming on Hulu)
Mom, I have to break it to you. Your son in high school was a felon. I snuck into Superbad, an R-rated movie, while it was in theaters when I was 16 years old. Then after that, thanks to my buddy Ryan Jenkins, I had a pirated version of Superbad on my video iPod. All of these scandalous moves is probably why I love this movie so much, but time has proven that Superbad is the quintessential coming-of-age comedy of the 2000s.
We follow Seth, Evan, and McLovin who are in their senior year of high school and are about to go to college. Their whole goal is to get laid before they go off to college. And to no one’s surprise they are using that “goal” to mask their insecurities of a friendship that is in danger of drifting apart between Seth and Evan. Plus, there is a blossoming friendship between Seth and McLovin.
Such scenarios lead to melodramatic drama from time to time, but Superbad turns it into utter hilarity. Seth and Evan are trying to impress their crushes by buying them alcohol and that sends them on a series of unexpected escapades. Seth and Evan are led to an adult party with a potential predator and McLovin gets escorted to the high school party by two incompetent and goofy cops after being attacked in a liquor store. Each different storyline brings laugh-out-loud fun that never stops. It’s a perfect rewatch movie and a surprisingly great date movie.
Streaming TV Corner
What we’re watching this week
Billy: I Think You Should Leave with Tim Robinson (streaming on Netflix)
This is a sketch comedy show that is perfect for the YouTube generation. Yes, it is streaming on Netflix, but Tim Robinson makes these sketches extra weird and I think he does this because of his time on SNL. There is no doubt that he is a talented writer if he wrote for SNL, but each sketch goes through an intense vetting process. Here it seems like he is creating the ideas that make him laugh and to that end some of the sketches do not land, but when they do I haven’t laughed this hard in a long time. Give this one a watch. It is such a breeze.
Links to get you hyped
It’s been five years since David Fincher last made a movie (2014’s very good Gone Girl). Finally, he’s coming back with a Netflix biopic of Citizen Kane screenwriter Herman Mankiewicz, starring Gary Oldman. More immediately, I’m doing my best to remain patient for the second season of Mindhunter.
Beyonce has blessed us with a new song for Disney’s live-action version of The Lion King. But, wait, there’s more! She’s also announced a new album called “The Lion King: The Gift,” which is “a variety of Lion King-inspired songs written by African artists” and curated by Beyonce. It’s out next Friday, the same day as the movie.
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