While 2023’s comedy release schedule looks a little light this year, per BBC, there’s still plenty of content due that is sure to put a smile on the faces of fans of the genre, including the new Barbie movie starring Margot Robbie and Ryan Gosling, as well as the remake of Disney’s Haunted Mansion, Legally Blonde 3 and the vampire-based horror comedy Renfield starring Nicolas Cage, which certainly looks interesting.
Looking back 23 years, however, to the turn of the century, comedy was in a different place. Seann William Scott was at the top of his game after the success of American Pie, and beloved actor Robert De Niro, best known for his tough guy dramatic roles, managed to make audiences laugh the world over, proving there’s no genre he can’t master.
Elsewhere, the Coen brothers released another masterpiece to add to their repertoire, and Owen Wilson appeared in two box office hits. Whilst it’s debatable how some of these films would be received today, it was certainly a fun time for comedy, and here are 10 of those movies that turn 23 in 2023.
10 Road Trip
DreamWorks
Very much of its time, Road Trip was the directorial debut of Todd Phillips, who went onto direct Old School, all three The Hangover movies, and the Oscar-winning Joker. Starring Seann William Scott and Tom Green at a time when both were genuine superstars, with Scott riding the waves of his success in American Pie and Tom Green and his Tom Green Show on MTV. This teen sex comedy basically follows the antics of a group of college kids as they embark on a cross-country road trip to retrieve an illicit tape mistakenly mailed to a girlfriend. Rude, crude, and, at times, utterly ridiculous, the movie was a box office hit at the time and spawned the obligatory direct-to-video sequel, which failed to live up to the hype of its predecessor.
9 Shanghai Noon
Touchstone Pictures
Jackie Chan and Owen Wilson star in this action-packed buddy comedy that juxtaposes the choreography and action found in traditional martial arts films, of which Chan is somewhat of a veteran, with the setting of the old wild west. The duo’s chemistry is really what carries Shanghai Noon, and the riffing between the two vastly different heroes never grows tired. The movie is inspired by the classic western drama Red Sun, starring Charles Bronson and Toshiro Mifune, but reimagined as an action comedy.
8 Dude, Where’s My Car?
20th Century Fox
2000 was a good year for Seann William Scott, with Dude, Where’s My Car? being his second entry on this list, this time starring alongside Ashton Kutcher in the role that propelled him from a successful sitcom actor into a certified Hollywood star. The movie itself revolved around the pair of stoners who, after a particularly reckless night of self-indulgence, are unable to remember and locate where they left their car the night before. Their adventure becomes more and more absurd as their search progresses, and they begin to gradually piece together the night before and encounter a number of weird and wonderful characters. A clear inspiration for The Hangover, the pair’s chemistry and the irreverent humor went down a storm with audiences and the movie becoming a box office hit, later going on to achieve cult status.
7 American Psycho
Lionsgate Films
When American Psycho, the novel by Bret Easton Ellis, was published in 1991, the book was a hit with a huge amount of controversy. In particular, the book was criticized by many for its misogyny and portrayal of violence against women, so it may be surprising to hear that the movie was, in fact, directed by Canadian director Mary Harron. To say she undertook the task successfully is an understatement. Herron interpreted it as the pieces of satire it was meant to be and as a result, American Psycho is one of the finest examples of modern horror comedies there is.
Harron was praised for her unique direction style, and it was noted that her off-kilter tendencies were a good complement to Ellis’ unique style. While comedy might not be the first genre that springs to mind when thinking American Psycho for many, it is certainly drenched as much in dark humor and satire as it is in blood and violence.
Set in the yuppie 1980s era New York, American Psycho follows up tight investment banker Patrick Bateman (played flawlessly by Christian Bale) as he begins to lose his grip on reality and descends into a mass murdering pit of madness. Obviously, due to the graphic and controversial nature of the source material, the movie had its detractors, but Harron’s grasp, and handling of the material perfectly brought to life the 80s culture of materialism, narcissism, and greed in a way in which all those in the project should be proud.
6 Little Nicky
New Line Cinema
Following Adam Sandler’s hugely successful run of comedy classics of the 90s, his popularity, along with critical opinion began to wane at the turn of the century. This is exemplified by Little Nicky and its tepid critical response and disappointing box office numbers. However, in the years since, the movie has found a place amongst Sandler devotees and is often thought to have been unfairly judged at the time. The movie sees Sandler playing the son of Satan, who is tasked with returning his two brothers to Hell and preventing a catastrophe of epic proportions.
Regardless of your views on Sandler’s unique brand of humor, one cannot deny that this movie features some of the greatest casting decisions ever made. There’s Harvey Keitel as Satan and Rodney Dangerfield as Satan’s father Lucifer, and an unforgettable cameo from Ozzy Osbourne as himself who saves the day by biting the head off of Satan’s first-born son while he is in bat form.
5 O Brother, Where Art Thou?
Buena Vista Pictures Distribution
The Coen Brothers have a pretty immaculate record when it comes to directing, with many arguing that their comedic output is often their greatest. Following the success of previous comedies Raising Arizona, Fargo and The Big Lebowski, the Coen’s recruited Hollywood A-lister George Clooney to star alongside a fantastic cast that include several previous Coen collaborators including John Goodman and John Turturro.
O Brother, Where Art Thou? delivers everything you’d expect from two of the most highly regarded directors in the industry. Set in rural Mississippi during the 1930s, the basic premise revolves around three escaped convicts on the hunt for hidden treasure while a sheriff relentlessly pursues them. Looking deeper, it becomes apparent that the movie is in fact a clever retelling of Homer’s epic Greek poem The Odyssey. There’s humor, heart, satire, plenty of drama, and a phenomenal folk/country soundtrack, which won the prestigious Grammy Award for Album of the Year (via Rolling Stone).
4 Meet the Parents
Universal Pictures
Comedy’s biggest success story was, without a doubt, Meet the Parents. The film received high praise from critics across the board and was the highest-grossing comedy of the year (as well as one of the highest-grossing across all genres). It chronicles a series of rather unfortunate events that plague Greg, a hapless nurse played in a career defining moment by Ben Stiller, while visiting his girlfriend’s parents. Whilst every cast member delivered a stellar performance, the real revelation came in the form of acting legend Robert De Niro as he appeared as the father, a role that played on his reputation as a no-nonsense tough guy to hilarious effect as Greg constantly tries, and fails, to impress.
3 High Fidelity
Buena Vista Pictures
A smart, engaging, and thoroughly entertaining adaptation of Nick Hornby’s novel of the same name, High Fidelity is arguably the movie that provided Jack Black with his breakthrough role. Yes, he’d been in many films beforehand, and, yes, it’s John Cusack playing the lead role, but this was the first time the world was really treated to the Black we’ve come to know and love. His role was substantial enough to leave a lasting impression in this critically acclaimed cult classic.
Both he and Cusack shine in this romantic, coming-of-(middle?)-age comedy, focused on the life of a record store owner (Cusack) as he looks back at his top five break-ups (including one in progress). Considered to be an extremely realistic portrayal of work life at a record store amongst those who’ve had the job, the movie has since managed to achieve somewhat of a cult status
2 Miss Congeniality
Warner Bros.
Sandra Bullock excels in Miss Congeniality as we witness her awkward and reluctant transformation from an FBI agent who lacks any kind of refinement and femininity to a beauty pageant contestant as she is forced to go undercover to thwart a terrorist plot that involves attacking the national Miss United States pageant. Bolstered by a fantastic supporting cast including several legendary faces such as Michael Caine, Ernie Hudson, and William Shatner, the movie is a lighthearted, feel-good flick that provides viewers with 100 or so minutes of easy go entertainment..
1 Bedazzled
20th Century Studios
2000’s Bedazzled has a lot going for it seeing as it was directed by comedy veteran Harold Ramis, and featuring the infectious charisma of Brendan Fraser and Elizabeth Hurley, not to mention the fact that it was a remake of the highly revered 1967 British film of the same name, written by comedy icons Peter Cook and Dudley Moore. And while on the whole it was a solid feature, many felt it ever so slightly missed the mark, focusing too much on the action and too little on the humor, preventing it from becoming the classic it should have been. It follows the tale of a man (Fraser) who sells his soul to the devil (Hurley) in exchange for seven wishes, which he hopes to use to gain the affection of a co-worker. Living up to her name, the devil gives the man more than he bargained for as his life begins to spiral out of control.
