I REWATCHED 12 CLASSIC 2000s COMEDIES – HERE’S WHAT HOLDS UP

We all have fond memories of films from childhood, but I disillusioned myself so you don’t have to!

I recently rewatched a dozen 2000s-era comedies that I once enjoyed, and experienced a surprising range of reactions. My conclusion? Sometimes it is best to let sleeping dogs lie… but also sometimes sleeping dogs are a man’s best friend.

Here are my reviews.

SCARY MOVIE (2000) – Maybe?

This style of humor isn’t really my thing, but it is undeniably done well. 

Scary Movie parodies practically every classic “scary” trope; as well as Scream, The Exorcist, The Blair Witch Project, I Know What You Did Last Summer, and too many more iconic films to list.

Personally, I was more disturbed by the gross body humor in this movie than the actual body horror it was satirizing, but I think that might have been part of the joke?

I would recommend a screening of Scary Movie on Halloween with a group of friends. And a lot of wine. Other than that, I’m not too keen to re-rewatch this one. 6/10.

LEGALLY BLONDE (2001) – Of course! The sheer warmth of spirit!

Reese Witherspoon is so sweet in this role that you can’t help but love Elle Woods. The impact of her kindness on others inspires hope for humanity and makes it even more satisfying to watch her succeed. Add in the film’s bubbly-bright color scheme and Elle’s iconic pink, shiny outfits, and “Legally Blonde” is literally a recipe for serotonin.

This movie has calmed me down from anxiety attacks. 9/10.

WET HOT AMERICAN SUMMER (2001) – Yes. Sweaty and surreal.

Taking place in the 80s on the last day of summer camp, the movie follows a group of counselors as each attempt to wrap up their own unfinished business. 

Coming in on the heels of now-archetypal teen sex comedies like American Pie, Wet Hot American Summer presented a spoof on the genre that was, if anything, ahead of its time. 

The movie’s awkward, deceptively lazy comedic style only highlights the talent of its cast – including a young Amy Poehler and Paul Rudd – and its elements of absurdism blend strangely well with the relatable adolescent camp vibes.

Critics were unenthusiastic about this movie, but I think they just couldn’t take the heat. 8/10.

SCOOBY-DO (2002) – Yes. Refreshingly mindless.

I can’t fathom why this 2000s knee-slapper has a 31% on Rotten Tomatoes! Ok so knee-slapper might be stretching it, but I personally have been a fan from childhood, and this film aged like a fine wine.

A live-action remake of the classic kids’ television series, Scooby-Doo follows the Mystery Inc. gang after they’ve grown up and split up. Chaos ensues when they all end up at the same island resort to investigate some mysterious and spooky business. Elegantly dusted with subtle weed jokes, and featuring what are still the weirdest monsters I’ve ever seen, it’s just adult enough to attract an older audience and just ridiculous enough to turn most of them right back away – the keyword here being most. 

I will admit that I can’t quite figure out the target audience here, but I do know I’m in it. Although Scooby-Doo was panned by critics for being “dumb” and “weird,” these are exactly the qualities I adore in this film. 9/10.

HOLES (2003) – YES. So good.

Shia LaBeouf stars as Stanley Yelnats, a teenager who is wrongfully convicted of a high-profile robbery. In lieu of jail time, Stanley is sent to Camp Greenlake, where juvenile delinquents are forced to mysteriously dig holes all day long in the desert. 

Off-beat and startlingly emotional, this movie was every bit as good as I remembered it to be. And also, that “Diggin’ Up Those Holes” song? An absolute banger. Dare I say…? 10/10.

ANCHORMAN: THE LEGEND OF RON BURGUNDY (2004) – Flawless. 

Great Odin’s Raven! I don’t know what I was expecting, but rewatching Anchorman: The Legend of Ron Burgundy was a decadence beyond imagination. To be fair, I might have been slightly drunk while watching it, but still! You can’t deny that Will Ferrell shines like the evening star in his legendary role of Ron Burgundy in “The Legend of Ron Burgundy.”

Ron Burgundy is San Diego’s top-rated newsman in the male-dominated broadcasting of the 1970s, whose perfect life spirals out of control when his network hires an ambitious new, female anchor. 

Rewatching Will Ferrell movies is always something of a trip and he, of course, plays his part in “Anchorman” to foolish, manic perfection. The film has aged like a fine cheese, its disorienting and deeply ironic style of humor far ahead of its time. If nothing else, rewatch it for the jazz flute scene. You won’t regret it. 10/10.

SUPERBAD (2007) – Yes! Charming and self-aware.

Jonah Hill and Christopher Mintz-Plasse shine in this clever coming-of-age comedy, but Michael Cera is its true star, showing off his talent for acting hilariously, realistically awkward. 

The film follows two best friends attempting to lose their virginity on the last night of high school, but “Superbad” brilliantly utilizes the trope to reveal its main characters. We become familiar with Seth and Evan’s quirks, their insecurities, and the strength of their bond as they face the challenges of growing up and maybe growing apart. 

To top it all off, this film doesn’t even objectify women! Easy 9/10.

BRIDE WARS (2009) – No. Bizarrely sexist.

This tale of battling bridezillas wins points for its talented actors and attractive sets, but boy is it ever offensive to women. 

The main characters are so shallow that they’re barely characters. Two lifelong best friends schedule their wedding on the same day and become instant enemies? What?? How did someone get Anne Hathaway and Kate Hudson to star in a storyline that would hardly hold up as a sitcom conflict, let alone a feature-length film?

Besides the fact that both characters are obsessed with their weight and appearance, there are gender stereotypes being upheld here that I had never even heard of. 3/10.

THE HANGOVER (2009) – Surprisingly not that bad?

Ok, definitely not a perfect movie, and much certainly does not hold up, but I found myself laughing along for a lot of it. 

The Hangover follows a group of friends who travel to vegas for a bachelor party two days before their buddy’s wedding. Mystery and hilarity ensue when they wake up the next morning with no memory of the night before and no trace of the groom-to-be. 

The main characters are perfectly cast– Bradley Cooper stands out for his godlike appearance and titillating performance as a bad-boy high school teacher, but Zack Galifianakis steals the spotlight as the socially awkward brother-in-law. 

Unfortunately, this film loses a lot of points in my book for 1. relying a bit too heavily on the slapstick aspect of 2000s bro-comedy and 2. a moderately upsetting stance on gender, race, and homosexuality. But it low-key gets away with it, as it at least seems to be more self-aware than other movies of its ilk.

Definitely dated, but worth watching in a very specific mood or setting! (read: drunk.) 6/10.

EASY A (2010) – No, unfortunately!

This one really disappointed me because I remember totally loving it. 

Of course, Emma Stone is fabulous as Olive, a wholesome young teen who is overheard lying about losing her virginity and becomes the new “school slut.”

The things I remembered the most about the movie were definitely still the best parts: mainly, a relatable sequence at the beginning where Olive becomes obsessed with a musical birthday card’s rendition of “Pocketful of Sunshine.” I also enjoyed the silly and adorably supportive dynamic of Olive’s family.

Unfortunately, much of the humor in this movie was pretty basic. I also fear that its creators wildly misunderstood the modern high school experience. Even ten years, being gay was hardly something to gossip about, and if rumors got around that you weren’t a virgin, it would be WAY weirder for people to actually care.

I do have to admire a modern adaptation of The Scarlet Letter, so I’ll give it a 6/10.

NO STRINGS ATTACHED (2011) – Nah.

It sucked. Sorry. I really do like watching these dumb, dated rom-coms, and I’m often entertained by movies that are actual trash, but this one wasn’t even fun to make fun of!

Natalie Portman and Ashton Kutcher star as two very sexy, lifelong friends who start hooking up on the condition that there are – surprise! – no strings attached. 

I don’t even want to talk about it, it was that stale. 

Despite the leading couple’s immense sex appeal, I couldn’t have cared less about them. Besides, 2011 also gave us “Friends With Benefits,” which is essentially the same movie but way better. 

Were it not for the hot people, “No Strings Attached” would rate far lower than a 5/10.

21 JUMP STREET (2012) – No. Icky.

I remember cracking up at this movie when I was in middle school, but in hindsight, I just feel like I shouldn’t have been watching it.

21 Jump Street follows best pals and irresponsible rookie cops Schmidt and Jenko, played by Jonah Hill and Channing Tatum, who are sent undercover as high school students to bust a drug ring. Jenko (Tatum) expects to be popular again, while Schmidt cringes to recall the days when his buff, mullet-clad future partner bullied him. 

But times have changed! 

It’s cool to be kind now, and the roles end up being reversed, with Schmidt attracting the attention of the environmentally friendly, drug-addled popular kids. I think it attempts to play on the whole handsome-vs-nice-guy trope, but they both just end up looking like total assholes: Jenko (Tatum) is whining half the time, and Schmidt starts dating a high school girl while pretending not to be an… adult… police officer?

There were a couple of amusing lines, but seriously guys, 21 Jump Street is way worse than you might remember. Questionable humor and weak plotlines aside, this movie is actually so disturbing. I didn’t even manage to finish – we had paused for a bathroom break halfway through when my friend abruptly recalled its final scenes, and neither of us wanted to see that again. 3/10.

Conclusion: Though they were some mega-flops, there were a handful of movies here that really tipped the scale in favor of 2000s flicks! Very suprising! Naturally, today’s social sensitives might dictate a distaste for this style of humor, so if you are easily offended, you might want to sit this one out. But personally, I think that many of our prepubescent faves are worth a rewatch!