Filmmaker Judd Apatow largely made a name for himself with the production of the cult teen “dramedy” show Freaks and Geeks. 1995’s Heavyweights and fan-favorite The Cable Guy from ‘96 helped put him on the map in the realm of movies. Yet, it was the breakout hits Anchorman: The Legend of Ron Burgundy and The 40-Year-Old Virgin in the early 2000s that made him a major player in comedy films.
These quirky laughers largely helped pioneer a unique type of comedic films. Drawing influences from sitcoms and adding some improvisational bits, this endearing style took relatable situations and added a wacky spin to them. These are further enhanced by dynamic, funny characters brought to life by comedic greats like Will Ferrell, Steve Carell, Seth Rogen, Jonah Hill, and others.
Let’s take a look at the 10 best and funniest comedy films produced and/or directed by Judd Apatow.
Walk Hard: The Dewey Cox Story (2007): 6.8
Many of Apatow’s films have a knack for poking fun at more typical, real-life adult or teen situations. Yet, 2007’s Walk Hard: The Dewey Cox Story more closely resembles the likes of This is Spinal Tap, satirizing the tropes of a rockstar’s life during the mid-to-late 20th century. Specifically, it uses the biographical drama Walk the Line as a template and springboard for its parodies and gags, drawing from events of music icons like Johny Cash, Bob Dylan, and Ray Charles as its influence.
Memorable performances by Jenna Fischer and the hilarious John C. Reilly really bring this laughter to life, as they convincingly play the roles of musicians and star-cross lovers.
Step Brothers (2008): 6.9
A film can often stand on the strength of its great performances, and this is largely the case with 2008’s Step Brothers. Similar to films like Talladega Nights, Will Ferrell and John C. Reilly both bring their comedic “A” game and play off each other tremendously. They take on the rose of 2 man-children living with their parents and getting into various shenanigans. Other standout performances include Adam Scott as the smug, well-off brother, as well as Richard Jenkins as the stern, agitated father.
In a sense, the film feels like an odd family sitcom - just with a raunchier, zanier Adam McKay and Judd Apatow spin on the concept.
Knocked Up (2007): 6.9
Comedies can provide tons of laughs whilst also providing an endearing and emotional narrative.
Such is the case with Knocked Up, a 2007 rom-com that stars Seth Rogen as a slacker who’s in over his head finding that, after a one-night stand with a woman he meets at a bar (Katherine Heigl), he’ll be a father. As you’d imagine, there’s plenty of that typical Seth Rogen and Johan Hill stoner-style comedy throughout.
Yet, it’s intermixed with a heartfelt tale of personal growth and a whirlwind love story as this unlikely couple must find a way to come together and adjust to this drastic life change.
Pineapple Express (2008): 7.0
Judd Apatow comedies often push boundaries in terms of style and narrative, and the zany action-comedy Pineapple Express, from 2008, is a prime example. Stoner buddies Dale and Saul, played respectively by Seth Rogen and James Franco, find themselves caught up in a crazy fight for their lives as they witness a drug-related murder.
After smoking what’s considered to be some of the most potent and rare pot in the world called “Pineapple Express,” a stray roach makes them targets of the drug lord Ted Jones (Gary Cole). With its fun blend of stoner comedy and thrilling action, there’s plenty to be entertained by in this zany romp.
Forgetting Sarah Marshall (2008): 7.1
This charming laughter manages to take the more typical premise of a romantic comedy and injects unique twists. With its visually pleasing Hawaiian settings and colorful cast - which include a TV actress, a rockstar, and a Dracula puppeteer - it’s more distinct than it lets on.
Forgetting Sarah Marshall revolves around a rather awkward and amusing love triangle (or a love “square”) between Peter, his ex, Sarah, and their new love interests played by Mila Kunis and Russell Brand. Jason Segel and Kristen Bell memorably play the roles of the ex-lovers who find themselves on the same Hawaiian resort while taking a vacation. Naturally, this leads to various shenanigans and funny moments as Peter attempts to get over his crushing breakup with Sarah.
Anchorman: The Legend Of Ron Burgundy (2004): 7.1
This older Jud Apatow production quickly made a name for itself among young adult audiences with its slew of funny personalities and general wackiness.
This is punctuated by Will Ferrell’s role as the quirky and smug anchorman himself, Ron Burgundy, and strengthened by performances by Steve Carell, Paul Rudd, and others. A rising star in TV broadcasting played by Christina Applegate threatens to shake up the male-dominated world of 70s reporting, setting the stage for various humorous gags and zingers.
While the sequels didn’t quite resonate with the large and passionate fanbase, this original hit from ‘04 is still widely regarded as an iconic comedy of the 2000s.
The 40-Year-Old Virgin (2005): 7.1
This 2005 hit wasn’t just a comedic flick, but a game-changer for the genre itself, grossing close to $178 million at the box office and largely making Apatow a household name. It helped establish a new style of comedy with its long runtime rife with hilarious characters, goofy gags, and a memorable plot to boot.
The movie stars a timid, somewhat naive man by the name of Andy whose work buddies seek to rid him of his virginity. What starts as a wacky “dude-bro” comedy with sex jokes and some improvised zingers crescendos into a heartfelt, dynamic love story.
Begin Again (2013): 7.4
Like Walk Hard, this comedy takes a more musical approach; though that’s really where the similarities end, as this 2013 film favors drama and in-depth characters over silly gags.
The film stars Keira Knightley and Mark Ruffalo, who play an upcoming singer-songwriter and struggling label executive. While they’re both a bit down on their luck, the fates conspire in their favor as they meet at a New York bar, deciding to collaborate together on music projects. The bond and co-dependence of these two protagonists really shines through and makes for a memorable musically-tinged drama.
It received namely positive critic reviews and was nominated for an Academy Award for Best Original Song, with “Lost Stars.”
The Big Sick (2017): 7.6
The Big Sick offers a creative and endearing take on a romantic comedy, helping it earn a number of accolades in 2017. The film revolves around 2 lovers of different cultural backgrounds, Emily (Zoe Kazan) and Kumail (Kumail Nanjiani). As such, there’s much potential for a gripping plot, dramatic obstacles, and heartfelt moments, and it delivers on these fronts.
This is really a tale of cultural unity - and our leads getting their families to warm up to their relationship - more so than the relationship itself.
The quirky, charming brand of comedy that Nanjiani brings enhances this rom-com. It certainly helps that it was loosely based on a real-life romance of the actor, with a screenplay written by him and his now-wife Emily. The zany Ray Romano further adds some character and humor, taking on the role of Emily’s father Terry.
Superbad (2007): 7.6
Often described as “American Pie” for the 2000s next generation, this coming-of-age comedy excels in being both hilariously lude and charmingly heartfelt. It stars Jonah Hill and Michael Cera as Seth and Evan, two teenagers who seek to lose their virginity before graduation. Various hijinks ensue as the boys, along with their even geekier friend Fogell, scramble to secure a plethora of booze for a party being thrown by their classmate Jules.
Bill Hader and Seth Rogen make this increasingly wacky film even more memorable in their role as zany cops who strike up a friendship with Fogell, known by his fake ID as “McLovin.”
