10 Worst Comedy Movies of the 2000s, Ranked

Every decade produces its share of comedy gems and duds, and the 2000s were no different. This was the era of parody movies and Paris Hilton star vehicles, Mike Myers flops and the Ben Affleck/Jennifer Lopez disasterpiece Gigli. Rather than genuine laughs, these movies relied on clichés, awkward humor, or outlandish premises. In many cases, they tried to push boundaries or capitalize on popular trends, but missed the mark completely.

With this in mind, this list dives into ten of the worst comedies of the 2000s, each notorious for its failures in humor, storytelling, or production. These films serve as a reminder that comedy requires more than big names or big budgets; it needs timing, creativity, and connection with the audience. All three are in short supply among the following flops.

10 ‘The Love Guru’ (2008)

Directed by Marco Schnabel

“I’m a love guru, not a miracle worker!” After offering diminishing returns with the Austin Powers franchise, Mike Myers sunk to substantially lower depths with The Love Guru, in which he plays a spiritual advisor aiming to help a hockey player (Romany Malco) win back his wife (Meagan Good) and, in the process, restore his reputation. While Myers’s eccentric character is meant to channel the same offbeat humor that made Wayne’s World a success, The Love Guru misses the mark with awkward stereotypes and crude humor.

The film attempts to mine laughs from Pitka’s bizarre advice and mannerisms, as well as skewering various celebrities, but the jokes feel repetitive and dated. They tend to be gross-out and focused on human anatomy, akin to scrawlings on a bathroom wall. A case in point is the gag about “Jack and the elephant”, which sounds like something one would hear on a playground. No amount of celebrity cameos can make up for this fatal flaw.

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9 ‘The Adventures of Pluto Nash’ (2002)

Directed by Ron Underwood

“Let’s blow this place sky-high!” The Adventures of Pluto Nash takes viewers to a futuristic moon colony where the title character (Eddie Murphy), a nightclub owner, faces off against a gangster who wants to take over his business. Despite the mammoth $100m budget and the solid supporting cast (Rosario Dawson, John Cleese, and Pam Grier also appear), the movie’s uninspired script and bland humor made it a massive flop.

The whole thing just comes across as rushed and cheap. The storyline is haphazard, with aimless scenes that rely heavily on unconvincing special effects, and the star is far from his A-game. His performance is sleepy and disengaged, perhaps because he sensed he was making a dumpster fire. As a result, The Adventures of Pluto Nash was a supernova-sized box office bomb, grossing just $7m. Murphy has since joked about its awfulness and poor reception, saying, “I know the two or three people that liked this movie.

8 ‘Epic Movie’ (2007)

Directed by Jason Friedberg and Aaron Seltzer

“This isn’t just any epic… it’s an epic mess.” The 2000s were very much the era of the parody movie, with flicks like Not Another Teen Movie and Scary Movie performing well at the box office. However, this subgenre also produced some spectacular duds like Epic Movie, which are jam-packed with pop culture references but painfully low on jokes. Story-wise, it’s about four orphaned characters as they stumble into a mishmash of cinematic universes, encountering exaggerated versions of iconic characters along the way.

However, the plot serves only as a vehicle to connect various gags and celebrity send-ups, lampooning everything from Harry Potter and Pirates of the Caribbean to Lord of the Rings and Borat. These films provide a lot of material for satire, but Epic Movie‘s humor never rises above the lazy, obvious, and, above all, tedious. Other than decent supporting turns by Jennifer Coolidge and Fred Willard, there’s not much here to justify a viewing.

7 ‘Gigli’ (2003)

Directed by Martin Brest

“Turkey time. Gobble, gobble.” The disastrous Gigli stars Ben Affleck as Larry Gigli, a mob enforcer tasked with kidnapping the brother of a federal prosecutor. When his plan goes awry, he teams up with Ricki (Jennifer Lopez) and the pair get up to all manner of hijinks. On paper, this all seems enjoyable, but shoddy execution and a confused tone kill any potential the movie had. The worst elements here are the lackluster chemistry between Affleck and Lopez, Al Pacino‘s over-the-top performance, and several awkward, cringe-inducing closeup shots.

On the script side, Gigli features heavy-handed plotting and laughable dialogue (several lines have become iconic among bad cinema aficionados). The critical hatred for this film was intense on release, earning it a host of Razzie Awards and seeing the film pulled from theaters after only three weeks. All told, it earned $7.2m against a $75m budget, making Gigli one of the least profitable movies in history.

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6 ‘Son of the Mask’ (2005)

Directed by Lawrence Guterman

“It’s a whole new mask, baby!” Son of the Mask ranks among the likes of Staying Alive and Highlander II: The Quickening as one of the worst sequels ever. It replaces the charismatic Jim Carrey with the subpar Jamie Kennedy as the main character Tim Avery, a cartoonist who comes into possession of Loki’s mask, leading to chaotic results when his son inherits its powers.

Unlike the first installment, which was goofily fun, Son of the Mask is joyless, relying on over-the-top CGI and lame slapstick. The exaggerated visuals and cartoonish sequences simply don’t resonate. Fundamentally, though, the fatal flaw is the absence of Carrey. He was a mix of entertaining and annoying in the first movie, while Kenney is simply annoying in this one. Finally, some of the scenes are actually not appropriate for kids, making one wonder who the target audience was meant to be.

5 ‘Who’s Your Caddy?’ (2007)

Directed by Don Michael Paul

“Time to take this course by storm.” Who’s Your Caddy?, a watered-down riff on Caddyshack, centers on C-Note (Big Boi), a hip-hop mogul who attempts to join a prestigious country club. The film leans heavily on stereotypes and relies on predictable jokes about class and culture clashes, failing to offer any fresh or clever perspectives. Instead of developing its characters, the film focuses on exaggerated antics and gags that have aged poorly.

The central conceit – the mismatch between C-Note and his pals and the snoot club members – gets old fast, and the movie serves up little to supplement it. There’s a third-act attempt at emotion and sincerity involving the protagonist’s late father, but even this comes off as rushed, gimmicky, and unconvincing. Consequently, Who’s Your Caddy? is simply boring and can be safely skipped. Oddly enough, the film has one notable fan in Bill Clinton. According to Todd Philips and Bradley Cooper, he “loves” it.

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4 ‘Pledge This!’ (2006)

Directed by William Heins

“Let’s get this party started!” Paris Hilton leads this one as Victoria English, a sorority president determined to maintain her chapter’s reputation. The crux of the narrative involves Victoria and a group of misfit pledges attempting to navigate the superficial world of Greek life. It’s the flimsiest of premises, brought down further still by weak performances, shaky writing, and unnecessary nudity.

The humor is decidedly mean-spirited in Pledge This!, lobbing insults in all directions and reducing pretty much every character to a stereotype. Simply put, it’s tasteless, from the crude lines to the exploitative, raunchy content, all of which is designed to draw attention rather than serve the story. The cheap gimmicks extend to the film’s marketing, which claimed to feature “Paris Hilton’s film debut”, despite the fact that she had appeared in House of Wax the year before. Not for nothing, Pledge This! holds a 0% rating on Rotten Tomatoes. What a trainwreck.

3 ‘Superbabies: Baby Geniuses 2’ (2004)

Directed by Bob Clark

“Babies are taking over.” The first Superbabies was one of the more unsettling comedies of the 1990s, and the follow-up is arguably worse. Superbabies: Baby Geniuses 2 revolves around a group of babies with extraordinary intelligence and abilities who attempt to thwart an evil media mogul’s plan. The concept is already absurd, but its execution makes it even more challenging to sit through.

For example, the visual effect that makes the babies talk is borderline creepy; very ‘uncanny valley’. In terms of the story, Bob Clark‘s (Black Christmas, Murder by Decree) direction doesn’t add any layers to the already thin plot, resulting in a film that feels more like a prolonged gimmick than a real comedy. Then there’s the humor and action, which doesn’t really seem aimed at younger viewers. For all these reasons, the Superbabies sequel is an actively unpleasant viewing experience. Unsurprisingly, it flopped at the box office.

2 ‘Disaster Movie’ (2008)

Directed by Jason Friedberg and Aaron Seltzer

“It’s the end of the world, and it’s as bad as it sounds.” The lamest of the 2000s parodies Disaster Movie, which tries to poke fun at apocalyptic films like Cloverfield and Twister. The plot, such as it is, focuses on a group of characters facing a series of catastrophes, though this is just a device to string together lazy pop culture references. Most of them would have been dated back in 2008 and are practically like hieroglyphics now.

Even more annoyingly, most of the movies and shows that are mocked don’t actually fall in the disaster genre. There’s also a parade of celebrity cameos, including everyone from Dr. Phil to Kanye West, though the movie doesn’t find much to say about that that’s new or particularly funny. The result is a disjointed series of painfully unfunny sketches, stitched together in an entirely haphazard fashion. The upshot of all this was that critics quickly canonized Disaster Movie as one of the worst films of all time.

1 ‘The Hottie & the Nottie’ (2008)

Directed by Tom Putnam

“It’s beauty on the outside, and something else on the inside.” When it comes to the worst comedies of the 2000s, it’s hard to top this dysfunctional Paris Hilton vehicle, which makes Pledge This! look fine by comparison. The Hottie & the Nottie follows Nate Cooper (Joel David Moore), who moves to Los Angeles to reconnect with his childhood crush, Cristabel (Hilton), only to find he must befriend her “unattractive” best friend, June (Christine Lakin), first.

What follows is a wince-inducing mess of bad jokes, amateurish storytelling, brazen body-shaming, and all-consuming shallowness. There’s also unrealistic, annoying dialogue and less than zero character negative. Despite the $9m budget, everything is cheap and half-baked. The acting is atrocious across the board, particularly from Hilton, who is barely tolerable. The finished product is equal parts dull and mean, to the point that its 91 minutes feel like an interminable slog. The Hottie & the Nottie represents the decade’s comedic nadir.

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