The 2000s gave us some unforgettable comedies, but they also unleashed a wave of R-rated disasters that make you question the very concept of humor. These films didn't just miss the mark—they crashed and burned in spectacular fashion, leaving audiences groaning instead of giggling. From star vehicles that nearly derailed careers to sequels that should never have been greenlit, here are the worst R-rated comedies of the decade, ranked.
1. 'Analyze That' (2002)
Sequels are notoriously tricky, and Analyze That proves why. The original Analyze This charmed audiences with the unlikely chemistry between Robert De Niro's mob boss and Billy Crystal's therapist. But this follow-up, directed by Harold Ramis, strips away all that magic. De Niro's Paul Vitti fakes a mental breakdown to get out of prison, landing back under Dr. Sobel's care. What follows is a tired rehash of gags that worked once but now feel forced and unfunny. Lisa Kudrow is wasted as Sobel's wife, and the convoluted plot—involving Vitti trying to go straight with disastrous results—just drags. It's a prime example of how even a stellar cast can't save a script that's lost its soul.
2. 'Deuce Bigalow: European Gigolo' (2005)
If the original Deuce Bigalow: Male Gigolo was bad, this sequel is an abomination. Rob Schneider returns as the hapless man-whore, now in Amsterdam to visit his friend T.J. Hicks (Eddie Griffin). When European gigolos start turning up dead, Deuce must clear T.J.'s name by re-entering the escort business. The humor relies on shock value: crude bodily fluid jokes, homophobic panic, and a parade of women with physical deformities played for laughs. It's mean-spirited, lazy, and earned five Razzie nominations. Schneider may have embraced the infamy, but audiences suffered through one of the most unnecessary sequels ever made.
3. 'Freddy Got Fingered' (2001)
Tom Green's absurdist train wreck is a cult curiosity that's aged like milk. Gord Brody (Green) is a slacker who moves back in with his parents and spreads a lie that his father is molesting his brother Freddy. The plot is an excuse for a barrage of gross-out stunts and deliberately offensive scenes. While some defend it as avant-garde, most viewers find it plotless and pointless. It's a relic of an era when shock humor could still get a theatrical release, but it remains one of the most painful comedy experiences of the decade.
4. 'The Love Guru' (2008)
Mike Myers attempted to channel his Austin Powers magic into a guru character named Pitka, but the result is a cringe-fest of stereotypes and flat jokes. The story follows Pitka trying to help a hockey player win back his wife and the Stanley Cup. With a cast including Jessica Alba and Justin Timberlake, it should have worked, but the humor is so tone-deaf that it became a punchline itself. It's a rare film that's universally panned, and it effectively ended Myers' run as a comedy superstar.
5. 'Epic Movie' (2007)
The Scary Movie franchise's parody formula hit rock bottom with this spoof of blockbusters like Pirates of the Caribbean and The Chronicles of Narnia. The humor is juvenile, the references are dated, and the jokes land with a thud. It's a cash grab that feels like it was written by a committee of bored teenagers. For fans of the genre, it's a painful reminder that not every parody deserves a green light.
6. 'Date Movie' (2006)
From the same team behind Epic Movie, Date Movie spoofs romantic comedies but forgets to include actual jokes. It's a rapid-fire series of pop culture references and gross-out gags that feel desperate. The film's only legacy is as a cautionary tale of how low the parody genre could sink. It's a slog to sit through, even for die-hard comedy fans.
These films remind us that R-rated comedy can be a double-edged sword. When it works, it's liberating; when it fails, it's a disaster. For more on the worst of the decade, check out our list of the 6 worst R-rated thrillers of the 2000s. And if you're in the mood for something actually funny, try 'Trying' Season 5 on Apple TV+.
