Perhaps no single person has had a bigger impact on the comedy landscape this century than Judd Apatow. Through the absurdly high number of television shows and films that he has written, directed, and produced—Apatow has created a genre unto himself, all while helping launch some of the biggest comedic stars working today.
Despite his current big and small screen success, Apatow’s relationship to comedy started long before he ever made a splash in film and television. Like many comedians and filmmakers, Apatow’s passion for his preferred art form started from a place of fandom. As a teenager in the mid-’80s, he became obsessed with stand-up comedy. He even managed to interview several comedians he idolized at the time, like Garry Shandling and Jerry Seinfeld, for his high school radio station. At the age of 17, Apatow began his own stand-up career, which he decided to quit at the age of 24 before eventually returning to the stage in the 2010s. One of the main reasons Apatow decided to quit stand-up comedy was because his career in writing was taking off. Around this time, he was a writer, executive producer, and co-creator of the short lived Ben Stiller Show, and went on to write and produce on The Larry Sanders Show as well. Apatow’s departure from the stand-up world coincided with his arrival in the world of film and television. In fact, Apatow’s first writing credit on a theatrically released film came just a few years after he left stand-up when Heavyweights—which Apatow co-wrote—came out in 1995. Although it was his first foray into Hollywood filmmaking, the Disney produced, family comedy is not necessarily a great indicator for what Apatow’s career would go on to look like. Even at the time, it seems Apatow knew he wanted to make different kinds of films. He has been quoted saying he had a vision for “fun, big, broad comedy and set pieces, the types that I had seen Jim Carrey do in movies…combined with a sensibility that’s grounded and human like you would see in a movie like Say Anything…, Fast Times at Ridgemont High, or Diner.” Early on, Apatow struggled to convince anyone to make the films he wanted to make. As we all know though, he would eventually be able to make his vision a reality and give us some of the most heartfelt, hilarious, and deeply personal films of recent memory.
Interestingly, the most notable aspect of Apatow’s filmography may not be the films themselves, but instead the time in which most of them were released. Despite the fact that he is still releasing major films today, (the reason I’m writing this blog is because his newest film, The King of Staten Island, is premiering on PVOD this Friday) Apatow has become the de facto poster boy for an era of comedy that no longer exists in Hollywood. In many ways, the name Judd Apatow is synonymous with a type of film that does not get made anymore. In the mid-’00s, Apatow became the king of the blockbuster, r-rated studio comedy. During an unparalleled run from 2005-2015, Apatow wrote, produced, or directed 12 movies that made at least $100 million at the box office. Nowadays, things like that just do not take place. The film industry has changed a lot throughout this century, but one of the biggest changes has come with the death of the traditional studio comedy.
Since the rise of internet content and streaming has led to less and less people interested in going to movie theaters, studios are not as willing to spend $20-$40 million on classic, simple-concept comedy films as they have been in the past. For instance, the teen comedies released nowadays look a lot less like the raunchy, not-overly-complex, $20 million Superbad and a lot more like the raw, quiet, $9 million The Edge of Seventeen. While both of those movies are immensely enjoyable, they are clearly very different when it comes to look and feel. Another change that has taken place to the comedy genre, that has less to do with financials, is the fact that audiences now receive their “comedies” hidden amongst more popular genres. It’s possible that the two biggest comedy films of the previous decade were the Deadpool movies. Obviously though, movies like Deadpool and Deadpool 2 do not resemble Apatow’s films at all. The increase in IP-driven content and the demise of the DVD industry has led to it becoming very difficult to make relatively cheap, funny films nowadays. In fact, an argument can certainly be made that Apatow’s rise is one of, if not the final chapter in the story of Hollywood blockbuster comedies. This is made evident by the fact that there has not been a wave of new, fresh-faced comedic movie stars since the group that Apatow helped make famous, which includes Seth Rogen, Jonah Hill, and others.
Names like Rogen and Hill are important to mention when discussing Apatow’s career. It’s nearly impossibly to overstate the impact he has had on so many young, gifted comedians and actors. Going as far back as the early days of Freaks & Geeks—when he had a hand in hiring James Franco, Seth Rogen, Jason Segel, Martin Starr, Linda Cardellini, and John Francis Daley—it has always been clear that Apatow has a great eye for talent. Throughout the first half of his career, Apatow seemed to have a strong interest in utilizing off-center and scarcely-seen actors in his films. As previously stated, he is at least partly responsible for launching and elevating many of the biggest comedic stars of the past twenty years including the aforementioned Rogen, Hill, and Segel as well as names like Paul Rudd, Will Ferrell, Steve Carrell, Kristen Wiig, Kevin Hart, and of course his wife Leslie Mann. Apatow has also always seemed interested in acting as a sort-of guru for young comedians by helping them create, find, or develop the project that is right for them. This has especially been true during the second half of his career. Apatow knows the best results come from tailoring the project to the star that is attached. Moreover, as his career moves forward, Apatow seems to genuinely enjoy assisting stars who are attempting to tell stories that are either passion projects of theirs or deeply personal to them. Whether it’s Pete Holmes with Crashing, Kumail Nanjiani with The Big Sick, Lena Dunham with Girls, Seth Rogen with Superbad, Jason Segel with Forgetting Sarah Marshall, Amy Schumer with Trainwreck, Paul Rust with Love, Kristen Wiig with Bridesmaids, or most recently Pete Davidson with The King of Staten Island, Apatow deserves a lot of credit for giving comedians a chance to tell their stories.
One particular impressive thing about the group of actors Apatow helped launch is that they seem to all enjoy working together over and over again. Seemingly, much of this is due to the way Apatow approaches his projects. He somewhat famously encourages improvisation on his sets, and is known for giving his actors the freedom to explore and try different things. Apatow’s looseness on set led to him and his collaborators not only building successful working relationships, but genuine friendships as well. This is not something that is commonly seen in the frequently harsh and competitive world of Hollywood filmmaking. Something to admire about Apatow and his team though, is the fact that they have always seemed to avoid drama, backstabbing, and jealousy. It’s clear that from the beginning of his career Apatow knew the importance of surrounding himself with the funniest and most talented people he possibly could, which has led to a lot of his success.
When looking specifically at the films Apatow has written and directed himself, it’s clear that the comedy he enjoys the most is mined from real life. Before he started helping other filmmakers, comedians, writers, and actors tell their own deeply personal stories, Apatow built his brand off of creating films that mirrored his own life in many ways. He used the art form of film to not only capture the essence of male friendships potentially better than any director before him, but to also explore his own anxieties about the world he lives in. The four films Apatow has both written and directed—The 40-Year-Old Virgin, Knocked Up, Funny People, and This is 40—are all examinations of things that are very prevalent in his life. Even though he made it after he was already married, The 40-Year-Old-Virgin allowed Apatow to inspect some of the anxieties he had related to sex and dating as a single man. Knocked Up is clearly a reflection on the fears about becoming a parent and the pregnancy process as a whole. Funny People is Apatow’s ode to his first love; stand-up comedy. And This is 40 is an exploration of the difficulties that come with parenting, marriage, and entering middle age. The genius in Apatow’s work is that he is always deeply connected to the stories he tells. The reason the “apatovian” style has become so easy to recognize is because there are few filmmakers that can create authentically hilarious films with as much heart as Apatow injects into his movies. That particular heartfelt quality all his films share wouldn’t be as successful, or even possible, if he was not so close to the stories he was telling.
Perhaps it’s important to note that Apatow’s films are by no means perfect. Each one of the movies he has directed certainly has its flaws. The success of his comedy varies across his films, some of his plots are weaker than others, he is not an overly-talented technical director, and there is a lot of truth to the most prominent critique of Apatow’s work: his runtimes are often too long. A case can even be made that the films he solely produces are superior to the films he writes and directs himself. With all that being said however, there is an undeniable warmth and comfort that comes with each one of Apatow’s movies. They may not be the most perfectly crafted films ever put on screen, but they are movies that resonate with the audience in such specific and truthful ways. They are also movies that viewers genuinely want to rewatch over and over again. As stated earlier, Apatow created his own genre and there is a reason why that genre has thrived for nearly 20 years. He knows how to entertain, but more than that, he knows how to create stories that connect with the people who watch them.
Before I get to my ranking of Apatow’s five narrative feature films, I want to briefly discuss his documentary work. I decided not to include the three documentaries he has worked on in my rankings because I felt the best way to look at Apatow’s career was by looking at his fiction films. That being said, Apatow has done some truly remarkable non-fiction work throughout his career as well. He co-directed a film for ESPN’s 30 for 30 series entitled Doc & Darryl, which chronicled the turmoil former baseball stars Dwight Gooden and Darryl Strawberry have faced throughout their careers and their lives. As a Mets fan, this film was especially interesting to me, but it is still a compelling rise-and-fall story even if you don’t care about the Mets, baseball, or sports in general. Apatow and co-director Michael Bonfiglio did an excellent job of capturing what life was like for these two athletes during their highest highs and their lowest lows. Apatow and Bonfiglio followed up Doc & Darryl with an intimate documentary focused on North Carolina band The Avett Brothers, entitled May It Last. Similar to Doc & Darryl, this is a film that manages to captivate viewers who may not be familiar with its subject. May It Last gives the audience a detailed look into the ways The Avett Brothers create their music, which I found fascinating. As somebody who loves music documentaries, I consider May It Last to be one of the best films made in that genre over the past five years or so. Personally, my favorite Apatow documentary is his most recent. It is 2018’s two-part, four hour HBO doc, The Zen Diaries of Garry Shandling. This film, made shortly after Shandling passed away, is a touching and fitting tribute to one of Apatow’s main comedy mentors. Not only is Apatow able to give us a deep insight into the life of the legendary comedian, but The Zen Diaries makes it clear just how big of an impact Shandling had on other comedians and the world of comedy in general. It’s fascinating to watch this film knowing it was put together by Apatow, because in many ways, he has taken over the guru role that Shandling played for so many young comedians. It’s inspiring to think about how Apatow has spent so much of his career doing for young comedians what Shandling used to do for him and so many others. If you’re a fan of comedy, The Zen Diaries of Garry Shandling is a must-watch.
Now, without Apatow’s documentary work out of the way, let’s unnecessarily take a bunch of meaningful works of art from a talented filmmaker and pit them against each other for no apparent reason.
5. Funny People (2009)
“You’re my best friend, and I don’t even like you.”
The film coming in at the bottom of my list is often seen as Apatow’s first major misstep as a director. 2009’s Funny People starring Adam Sandler, Seth Rogen, Leslie Mann, Jonah Hill, Eric Bana, Jason Schwartzman, and Aubrey Plaza was the highly anticipated follow-up to 2007’s smash-hit Knocked Up. Unfortunately, this film did not garner the same praise that Apatow’s two previous films had received. Personally, I have an interesting relationship to this film because while I think it is Apatow’s worst, I also consider it to be underrated. I’ll explain that more in a moment but let me first touch on why this movie ended up in last place on my list. Funny People, more than any other film in Apatow’s oeuvre, suffers from his tendency to make movies that are too long. This film’s runtime is nearly 150 minutes and it seriously hurts the overall enjoyment of the final product. One of the main issues that led to that runtime is that this film does not totally know what it wants to be about. As I mentioned earlier, this film is Apatow’s love letter to stand-up; It is also about how going through a life-threatening disease can affect someone; It is also a romantic film about the complicated and sometimes destructive process of returning to “the one that got away”; It is also in some ways a meta-commentary on the real life of its star, Adam Sandler. Clearly, this film has a lot on its mind. Some have described as two movies in one, but I think it would actually be more accurate to refer to it as three or four movies in one. Here’s the thing, I actually think those three or four stories would work well on their own, but when crammed together, they’re just not very successful. The entire third act feels like a different movie than what came before it, and the film comes to a screeching halt once it reaches Leslie Mann’s character’s house. Despite all of these flaws, I enjoy a lot of things about Funny People. As I mentioned earlier, I genuinely think this film has become underrated. Although many of the criticisms are just, I feel they have overshadowed all the good qualities that can be found in this film. For instance, there is a lot of successful comedy found in the first two acts of this movie and the chemistry between Rogen and Sandler is legitimately great. It’s important to highlight the work Sandler does in this movie because this is truly some of the best acting he has done in his career. Interestingly, I find that this film doesn’t get mentioned when people talk about Sandler’s “serious” roles as much as Uncut Gems, Punch-Drunk Love, The Meyerowitz Stories or even Spanglish does. It absolutely deserves to be grouped in with the best work of Sandler’s career though. It’s fascinating to see him navigate his way through a role that feels so self-reflective. All in all, Funny People is far from the best movie Apatow has ever made, but there is still a lot of good stuff in it. If it were 40 minutes shorter and little more focused, it could have easily found its way near the top of this list.
4. Trainwreck (2015)
“Don’t get all threatened just because you don’t understand the concept of marriage!”
Apatow’s 2015 film starring Amy Schumer is notable for a variety of reasons. First, it is the only film Apatow has directed that he did not write, and that includes The King of Staten Island. Trainwreck was truly Schumer’s project from the beginning. It is based on her life, her stories, and her on-stage persona. Another reason this film is notable is because, while all of Apatow’s movies have elements of romantic comedy, Trainwreck is his film that fits that genre the most. In fact, perhaps the reason this film works as well as it does is because of how focused it is. Unlike the meandering Funny People, Trainwreck follows one single story from beginning to end. That story is an exploration of what happens when a commitment-phobic woman named Amy (Schumer) meets and falls in love with a “good guy” named Aaron (Bill Hader). As opposed to Schumer’s character, the story is not overly complex. It is quite simple actually, but it is also endearing, heartfelt, intimate and filled with laughs. Most romantic comedies hinge on the chemistry between their two leads and Trainwreck is no exception. There’s no doubt in my mind that this film would not work as well with different actors in the lead roles, but both Schumer and Hader knock it out of the park in this movie. Trainwreck allowed Schumer to prove that she can be a legitimate movie star—even if her following film work has not worked as well—and it allowed Hader to prove what we learned from the entirety of his work from this past decade: Bill Hader can pretty much do anything when it comes to the world of comedy. Trainwreck‘s supporting cast—which includes Colin Quinn, Brie Larson, Randall Park, Vanessa Bayer, LeBron James, and Mike Birbiglia—are all excellent as well. The reason why this film ranks lower on my list is because I find there are less laugh-out-loud moments than some of Apatow’s other works. Truthfully, this ranking has less to do with how I feel about Trainwreck and more to do with how I feel about the other films in Apatow’s filmography.
3. This is 40 (2012)
“All of a sudden we’re a magnet of negativity. What did we do?”
I’m aware that this is a slightly controversial take, but I really enjoy This is 40. This film is without a doubt the most personal film of Apatow’s career. Not only does it star his real-life wife and kids in prominent roles, it is very much centered on his relationship to parenting, marriage, and getting older. While I understand the complaints about this films length, irritating characters, navel-gazing quality, and its depiction of “rich, white people problems,” I can’t deny the admiration I have for how truthful and honest this film feels throughout. Most of Apatow’s films simultaneously have one foot in the worlds of absurd and sincere but This is 40 is much more raw, and in some ways dark, than anything else he’s ever made, with the possible exception of Funny People. It seems that Apatow used the lessons he learned on Funny People to make This is 40 a much more successful film though. Admittedly, this film is not nearly as enjoyable to watch as something like Trainwreck or The 40-Year-Old Virgin. I think it is unfair for people to hold that against this film though. It is about a marriage at its breaking point, it’s not supposed to be a happy, fun time from start to finish. Much like in all Apatow films that Paul Rudd and Leslie Mann appear in, I find them both to be incredibly captivating in this film. The trio of Apatow, Rudd, and Mann have obviously worked together a great deal throughout their careers, which must have come in handy when telling a story as personal and intimate as This is 40. Although the comedy in this film may not be as great or wide-spread as Apatow’s other works, it is used very effectively. Due to the nature of this film’s plot, the comedy in This is 40 feels like a welcomed distraction and breath of fresh air for the audience, much like it would for the characters who are living in this story. This is 40 is not a perfect movie and I understand if people disagree with my ranking. However, I have a lot of respect for how vulnerable Apatow was able to get with the making of this film.
2. Knocked Up (2007)
“Life doesn’t care about your vision. You just gotta roll with it.”
Usually when I write these “Ranked” pieces, I know going in what my top two or three films have to be. The other entries on the list may be interchangeable but the best of the best are often solidified from the start. This was true for filmmakers like Paul Thomas Anderson, Cameron Crowe, Wes Anderson, Sofia Coppola, and The Safdies—and it is true for Apatow as well. When I decided to write this blog, I knew Knocked Up and The 40-Year-Old Virgin would be taking the top two spots on my list. Both of these films are just a notch above everything else Apatow has directed over the years. While I think everyone is in agreement on that when it comes The 40-Year-Old-Virgin, Knocked Up seems to be slightly more controversial. There are some film fans out there who do not hold this movie in high regard. One of those people, Katherine Heigl, is actually one of the film’s leads but I’m not here to talk about that. I do believe that if you are unsure how you feel about Knocked Up but have not seen it in a long time, then it is worth a rewatch. I’ve seen this film many times in my life but I have found my appreciation for it increasing on more recent viewings. In some ways, this film is a template for the types of movies Apatow would go on to make throughout the rest of his career. The screenplay is smart yet ridiculous, and silly yet heartfelt. Knocked Up obviously has a lot of great observations related to pregnancy, and becoming a parent but it also has a lot to say about what it is like to grow up in general. That is something I think some people who have not seen this film in a while will be struck by when they rewatch it. It is something I was unaware of when I first watched this movie as a young teen. Now, as a 23-year-old, even though I am still fairly young and hopefully a long ways away from my first child—this film greatly resonates with me. Despite Heigl’s complicated relationship to this movie, she is genuinely terrific in it and her chemistry with Seth Rogen is one of the best things about this film. The chemistry amongst Rogen’s character and his group of friends is another thing that makes this film truly special. Even though it’s a hysterical comedy, not a lot of films are able to capture the feelings that come with grand life transitions as well as Knocked Up.
1. The 40-Year-Old Virgin (2005)
“You know what? I respect women! I love women! I respect them so much that I completely stay away from them!”
That’s right, Apatow’s directorial debut still remains the best work of his career. The 40-Year-Old Virgin is the film that launched both Apatow’s career and an entirely new decade of Hollywood comedy. One of the most impressive qualities of this film is just how well it holds up today, despite it having a bevy of dated elements to it. These elements not only include some problematic jokes that you would not find in a 2020 comedy, but also the use of landlines, VCRs, and “We Sell Your Stuff on eBay” stores. The reason none of those things affect the enjoyment of this film in 2020 though, is because the themes found in this movie are timeless. Even though Apatow would get more personal and more dramatic with some of his later films, The 40 Year-Old-Virgin contains some of the best heart of any of his movie. Even as far back as 15 years ago, it was difficult to make a romantic comedy that felt like a fresh take on the genre, but that is exactly what Apatow and Steve Carrell gave audiences with this film. I mentioned Carrell’s name there because some forget that he actually co-wrote this film with Apatow. This undoubtedly helped the overall product, because it’s clear that the main character of Andy was a byproduct of Carrell’s brain as much as it was Apatow’s brain. They constructed this character and this story together, which helped make this movie a success, and make this world feel lived-in for the audience. I’m hopeful that Davidson and Apatow’s collaboration on The King of Staten Island script leads to the same kind of success. It’s also important to highlight the supporting cast in this film. The 40-Year-Old Virgin introduced many moviegoers to people like Seth Rogen, Paul Rudd, Jonah Hill, Kevin Hart, Mindy Kaling, and Kat Dennings. In many ways, Apatow established his cinematic universe with this film. I also want to give a shoutout to Romany Malco who gives one of the funniest performances found in any Apatow film in this movie. There’s not a lot to be said about The 40-Old-Virgin that hasn’t already been said before. It started Apatow’s career and launched an era of comedy that would change the genre forever. More importantly for this list, it remains Judd Apatow’s greatest achievement as a director.