10 Iconic 2000s Comedies That Aren’t Funny Anymore
The glorious 2000s gave us certified classics like Anchorman, Superbad, and Mean Girls, but for every gem, the decade also served up a full course of crappy comedies that should never have been made. These films lean on tired premises, confuse “offensive” with “edgy,” worship pop-culture references like golden calves, or just forget what a joke is.
If you’ve ever wondered why your rewatch turned into a guessing game of “Why am I watching this?”, here’s the hall of womp-womp fame.
Dumb and Dumberer: When Harry Met Lloyd (2003)
Who would have guessed that prequels can be unsatisfactory, and that casting two C-class actors couldn’t replicate the chemistry of Jim Carrey and Jeff Daniels? This high-school origin story delivers a tragic lesson: the original Dumb and Dumber wasn’t just silly—it was lightning in a bottle. Without the leads’ top-notch facial expressions and perfect comedic timing, you’re left with a “huh” and a “whuh.” It’s the cinematic equivalent of a deflated fart cushion.
Son of the Mask (2005)
Who in their right mind thought that we needed a sequel that replaces Jim Carrey’s rubber-faced chaos with uncanny 2005-era CGI? Even kids wouldn’t laugh at this atrocity. The plot is just a baby doing weird stuff wearing the magical mask, and the tone flips between “Saturday morning cartoon” and “tech demo gone rogue.” The original was a slapstick goldmine; this one is just… sad.
The Hottie & the Nottie (2008)
This “comedy” tries to preach the “inner beauty” lesson while dunking on a character’s looks because it thinks that’s humor. Even the rom-com beats are boilerplate, and the gags are all raunch, no wit. Let’s not even mention the “transformation” arc because it’s so clumsy, it ruins the entire movie. If there’s a laugh, it’s the nervous kind you have when someone says something wildly inappropriate at a work party and you don’t want to offend them.
Kangaroo Jack (2003)
Marketed as a goofy talking-animal romp, this movie did the cinematic equivalent of catfishing. Remember the rapping kangaroo clip in the trailer? That’s basically a dream sequence. The plot is actually about two knuckleheads running cash for the mob in Australia, only to lose it to a very normal, non-chatty marsupial. It’s like ordering a pizza and getting a boring old celery stick instead.
Pledge This (2006)
A National Lampoon badge used to mean something. Here, it’s pasted onto a sorority comedy whose main innovation is “What if everything was shinier?” Paris Hilton stars as the queen bee on a quest for “Best Sorority” glory, while recruits endure hazing so cartoonish it feels like a parody of a parody. None of the jokes land, there’s no plot, and the whole thing feels like an extended reality-TV B-roll.
Eight Crazy Nights (2002)
Adam Sandler’s animated holiday musical takes the usual Sandler man-child arc and cranks it up with cartoon physics and noisy side characters. Maybe if the whole movie had been shorter, some bits might have landed better. Animation magnifies everything: the sentimentality gets syrupy, the obnoxiousness gets even more unbearable, and the songs, well, they’re actually fine.
The Master of Disguise (2002)
Dana Carvey is pretty good at doing impressions of people, but why would someone think that we needed a movie about that? We got a secret family of disguise experts who will use their talents to save the world, and that “family” exists mostly to put Carvey from one costume to another. Now, if the writing were better, maybe this could work. Instead, sketches ramble, the timing on the jokes feels off, and the 80-minute runtime feels like an eternity.
Disaster Movie (2008)
From the “endless pop-culture spoof” factory comes a film that promises Armageddon and delivers Celebrity Cameo Bingo. Rather than parodying disaster flick tropes, it points at whatever was trending in 2008—”Look! It’s that actor from a popular movie or show!” Even at release, the jokes felt like ancient memes.
Superbabies: Baby Geniuses 2 (2004)
Just look at that title for a second. If you’re fine with what you see and still want to watch it, there’s something wrong with you. Genius infants get superpowers and fight evil adults! Wow, that’s… cute? The script attempts to achieve family-friendly wackiness but ultimately results in confusion. The only truly successful gag is the audience asking, “How did this get made?” That question is doing Olympic-level comedy work.
The Love Guru (2008)
Mike Myers is a legend, but even legends have their moments. As Guru Pitka, Myers delivers a blizzard of pun-based wisdom, bodily-function “jokes,” and spiritual satire that nobody asked for. The movie leans hard on jokes that were already iffy, then repeats them like your uncle at Thanksgiving, thinking you must not have heard him because why aren’t you laughing yet?