There was a time when the name Judd Apatow was seen as a stamp of approval in the comedy world. Having been bumming around the industry for almost 30 years, he came to prominence with The 40-Year-Old Virgin (2005), a film that revolutionized the comedy format for better or worse, turning stories into feature-length improvisational segments that mixed pop culture references and stoner humor with a deeper, sympathetic heart that’s gotten him some comparisons to sentimentalist directors like James L. Brooks. He is the premiere filmmaker responsible for the modern man-child as well as launching such esteemed careers as Seth Rogen, James Franco, Jason Segel, and (to an extent) Steve Carell.
With his latest film The King of Staten Island (2020), it feels like a good chance to remember how far-reaching his influence is. While he’s gone from making personal comedies to passion projects for various up and coming comedians (see also: Amy Schumer’s Trainwreck (2015)), the results have spoken for themselves and proven that he still has some prominence in the industry. Will he finally make sense of Pete Davidson? Early reviews suggest that he kind of gets there, or at least taps into something endearing about his slacker approach to humor.
He is also a figure who is formative to how I see comedy, and for a time he was someone who I saw all of his work. Whether it was because he directed, wrote, produced, or even had a brief cameo in, I was there. Even if the track record is spottier these days, I am still curious to see how he’s helping to give the younger generation a chance to express themselves, mostly on TV with shows like Girls and Crashing.
With that said, he was too prominent of a figure in comedy to ignore and his body of work since 2000 alone could fill up a Top 40. That is why it’s difficult to narrow everything down, so I’ll do my best to look at his work in all of its varied forms and determine what my favorite projects of his are. Everyone’s tastes differ, and considering his impact on the industry there’s a good chance that you’ll have one or five that you’ll disagree with. Whatever yours are, feel free to leave them in the comments, and let’s get ready to take on the master of the heart-filled dirty comedy’s latest project.
1. Funny People (2009)
Prior to more recent films like The Meyerowitz Stories (2017) and Uncut Gems (2019), this was a film that made many wonder if Adam Sandler was capable of more complicated roles. It’s true that this isn’t much of a stretch as far as characters (a popular stand-up comedian who wasted his potential on mediocre movies), but what he does with the role is an endearing self-portrait, reflecting on mortality and the potential that his whole life has been a waste. The film is chock full of memorable cameos, proving that Apatow has some great connections in Hollywood, and is responsible for helping to launch the careers of Aziz Ansari and Aubrey Plaza, or at least allowing them to tell a few jokes.
It’s also the litmus test that determines how much you like Apatow. The film ranks among his longest, with the second half being exceptionally different at times in tone. For a film about stand-up comedians, the choice to add in a dramatic plot reminiscent of F. Scott Fitzgerald’s “The Great Gatsby” may seem confusing to some. However, those who can appreciate its diverse landscape will appreciate this as Apatow’s most dramatic and earnest film, finding autobiographical elements seeping into unexpected corners. Whereas This is 40 (2012) was too personal and distanced himself from audiences, Funny People was a perfect balance, managing to always be charming even when it wasn’t funny.
It was clear that the 2000s belonged to Apatow more than other comedy director, and it’s interesting to see him end the decade on a divisive entry. It was the previous generation coming to terms with the new guards, and it’s easy to see how good his eye for talent was. Most of the people here have only become more popular in the decade since. Pound for pound, it has some of his greatest cameos (James Taylor) and his best jokes. As far as stand-up movies go, there’s few that feel as lived in like this. This is as much a special film in his career as it is with Sandler, who has rarely felt more personable and interesting in his career.
2. Anchorman: The Legend of Ron Burgundy (2004)
Before anyone had any idea who Apatow was, they were familiar with this Will Ferrell vehicle that took the improvisational technique and turned it into an art form. At the time it received the reputation as one of the most quotable films in history, and it’s easy to see why. For a good few years, there were few characters as imitable as Ron Burgundy whether it be his catchphrase (“You stay classy, San Diego”) or the random cut to Starland Vocal Band’s “Afternoon Delight.” So much about early-00’s comedy can be found in this film, and the endearing execution redefines laugh-a-minute to such an extent that they even had enough outtakes that made up a whole additional narrative called Wake Up, Ron Burgundy (2004).
It was a showcase for so many careers at a pivotal time, and it remains the point where director Adam McKay became his own powerhouse, going on to make the influential comedy website Funny or Die while using humor to secretly tackle bigger issues. You wouldn’t believe it, but his take on the man-child is far more profound than any entry that Apatow has personally directed, finding ways to make the undermining of women in the journalism industry into hilarious comedy with an ultimately fulfilling message.
Anchorman more than any other film in the extended Apatow universe has created an unexpected franchise that still goes strong to this day. Not only is there an Anchorman 2 (2013) – with three alternate versions of its own – but Ron Burgundy has his own podcast. There’s a fondness for this character that refuses to go away. It’s the start of an amazing partnership between McKay and Ferrell and showed that part of Apatow’s charm was allowing these voices to speak for themselves, literally, for hours at a time. Sometimes you strike gold, and this is the peak of the whole enterprise.
3. Forgetting Sarah Marshall (2008)
Having been the awkward sidekick in other Apatow films, Jason Segel’s penned romantic comedy took the R-Rated humor in its deepest and most vulnerable possible direction. He’s almost too good at playing a sad sap, finding a trip to Hawaii being derailed at every turn when his ex is there with her new boyfriend, making everything feel all the more uncomfortable. Segel pulls from personal experience to make the film one of the most honest depictions of love. It’s a romantic comedy with realistic stakes, appearing from the man’s perspective as his life falls apart and everything feels so soul-crushing. Rarely have sex scenes been so awkward.
While it had an admirable sequel with Get Him to the Greek (2010), the original will always be better for how it took a genre associated with hollow stakes and found a deeper heart, featuring one of Mila Kunis’ funniest roles to date. It’s a goofy film that not only reflected Segel’s charisma but found his nerdy love of puppets producing the memorable song “Dracula’s Lament” and proving that he was just as funny as the more prominent Apatow stable of actors at the time. The only difference is that he was more insular, willing to look at the emotional complexity of these damaged men, and the work speaks for itself.
4. Bridesmaids (2011)
If there was any overstated achievement of the 2010s, it was the gargantuan shift in how studio comedies were made. Prior to Bridesmaids, the argument as to whether women were funny was considered a serious debate that got too much traction out of the fact that there were few R-Rated comedies lead by women. Leave it to Kristen Wiig's vehicle to prove everyone wrong, featuring an exceptional supporting cast that subverted the rom-com tropes and found the feminine perspective on gross-out humor revolutionizing the entire framework. It questioned female friendship in refreshing ways, finding the heart to be just as rich as any other Apatow vehicle, but with its own inspired twist.
This isn’t just a film that proudly declared that women were funny, it was an endearing story of feeling insecure when your friends are more successful than you are. It’s the struggle to feel like your personal ties matter. It’s tender, reflective of a struggle not often seen in a film. It was the start of a more diverse and personalized take on romantic comedies, and one that’s been duplicated dozens and even hundreds of times since. Even then, there are few that achieve as effective of a joke rate as this film, which deservingly lead to Oscar nominations (the first for any Apatow-related project). For a genre that’s been largely dying, Apatow has done plenty to make it feel more vital and relevant than ever before.
5. Superbad (2007)
Back in 2007, you couldn’t go more than a month without hitting an Apatow film. Following the runaway success of Knocked Up (2007) that turned Seth Rogen into a leading man, this August release did the same for Jonah Hill and Michael Cera as they took a story of underage drinking to profound heights. It may be the grossest, most profane coming of age story in existence (the closing credits alone feature dozens of phallic drawings), but it’s also one of the most endearing looks at young male friendship, finding two friends coming to terms with their final days together. Soon they will be at different colleges, leaving them alone with their own awkward personalities.
While the film received attention at the time for launching Christopher Mintz-Plasse’s career, its real achievement was being Emma Stone’s cinematic debut. Even then she had a great deadpan delivery that managed to crash the boy’s club and make this a battleground of comedy. Every performer in this gets a handful of memorable moments, and it also helped to launch the writing careers of Rogen and Evan Goldberg, who wrote this screenplay as teenagers (though again, it was largely improvised). If any film confirmed that the Apatow era was only getting started, it was this film that proved that everyone young and old could play the game and have a good time doing it.
BONUS
Walk Hard: The Dewey Cox Story (2007)
Despite being the biggest comedy producer in the world at the time, it’s interesting to note that Apatow was capable of creating a cult hit. Many have credited Walk Hard as being a film so scathing of music biopics that it killed the genre (or should’ve, anyway), and for good reason. The film serves as John C. Reilly’s funniest movie as he takes on a genre that has been soured with bad tropes, all lovingly mocked here with a soundtrack that is filled to the brim with humor while also working as believable standalone songs. Not since This is Spinal Tap (1984) has a joke song felt this inventively layered. It may be one of the wackiest films in his entire career, but that only adds to the wonderful absurdity on display.
What are your favorite films from Judd Apatow? Given that he’s continually produced projects of varying subjects, it’s likely that your list will greatly differ from mine. As I mentioned that the top, he’s made so many odd ducks that I could easily branch this out into a list that’s five times as long. Who knows, maybe The King of Staten Island will rank fairly high on that list. It’s not unlikely. I still believe that his name is a positive stamp for comedy, even if the quality of his projects are all over the place. At the end of the day, he knows a good joke when he sees it, and I’m willing to listen to the ones he thinks are worth telling.
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