If there was a comedy movie released in the past decade or so that you enjoyed, it was more than likely produced by Judd Apatow. He began his career as a standup comic before finding his calling as a filmmaker and producer. He discovered Seth Rogen and Jonah Hill and Paul Rudd and Jason Segel and James Franco and Danny McBride and, well, the list could go on indefinitely. Apatow knows comedy talent, and he has used this skill to get movies by talented people made and fill them with even more talented people. Here is every Judd Apatow production, ranked from worst to best.
23. Drillbit Taylor
Any character that Owen Wilson plays is going to be likable. That’s just a fact. There’s no way, really, that Owen Wilson can’t be likable. He has the smile and the charm and breezy comic talents to make you fall in love with him in any role. That makes this comedy movie about a bodyguard who is hired by some geeks to protect them from the bullies at their high school at least watchable. But even with a screenplay written partially by John Hughes, this movie is unfunny, uninspired, and too much of a retread to stand rewatches.
22. Year One
Boy, what a disappointment this was. A comedy about cavemen directed and written by Harold Ramis starring a cast of comedy legends like Jack Black and David Cross and Michael Cera and Paul Rudd and Hank Azaria and Bill Hader sounds like it should be the funniest thing ever. But sadly, it was not. Sure, it has its moments, but in the end, it just feels like a lazy, sloppily put together, mediocre, middling affair. Such a wasted opportunity. This could’ve been a modern day attempt at Mel Brooks’ style of film comedy. Well, in a way, it was – it was just a failed attempt.
21. Pee-wee’s Big Holiday
This movie was sort of fan service for Pee-wee Herman. If they were big fans of the character and had been yearning to see him again, then they could enjoy this movie. It was made for them. So, your enjoyment of the film – needless to say – all depends on where you stand on Pee-wee Herman. If you find him annoying, you’ll hate the movie. If you find him endearing, you’ll love it. It’s pretty simple. As a movie, it’s quite light on laughs and its plot is quite simplistic.
20. Begin Again
Before working with Judd Apatow on this musical dramedy starring Keira Knightley and Mark Ruffalo, director John Carney had made a name for himself in small, raw, real, personal, intimate, unique indie pieces. Here, sadly, that personality goes completely out the window and all we get is the kind of trite, overproduced Hollywood fare that Carney tends to avoid. It’s a shame, because both Carney and Apatow (and Knightley and Ruffalo, for that matter) are capable of better than this. Still, the movie’s heart is in the right place.
This story of two city dwellers who reconnect with one another and with themselves when they move into a hippie commune in the middle of the woods has an interesting premise, sets it up well, and has some very funny moments. Sadly, it’s just not as strong as David Wain and Paul Rudd’s previous collaboration, Role Models. Paul Rudd and Jennifer Aniston make for a good screen pairing, which keeps the movie enjoyable for its whole runtime, but this isn’t destined to be a timeless comedy classic.
18. The Five-Year Engagement
In this movie, the chemistry of Jason Segel and Emily Blunt is fantastic and a lot of the jokes and gags land. The troubled romance feels sadly realistic and it gets off to a very strong start. The only problem with the movie is that it goes on for too long. It drags on and on. This is suggested in the title, since the engagement lasts for five years, so the movie has to cover five years. But maybe two or three years would’ve been more manageable. But then the comedy would suffer, because a lot of engagements last that long. Segel growing a mountain man beard and losing a toe to frostbite is funny, but the movie should’ve resolved the couple’s issues at around this point. It went on for about another half an hour after that, which should’ve been cut down. Otherwise, it’s great.
17. This is 40
The problem with This is 40, the sort of spin-off/sequel to Knocked Up, is that it all feels too real. Judd Apatow captured the frustrations of marriage and the struggles of parenthood and all the arguments and the resentment and the conflicts that come with it a little too well. So, at a certain point, you can’t laugh at it, because it is simply reflecting too much truth. If you’re a parent or a spouse or simply pushing forty, then this movie isn’t a comedy – it’s a horror movie. But still, you can hardly say that a movie capturing its subjects too well is a bad thing. And the scene with Melissa McCarthy improvising and riffing in the principal’s office is absolutely hysterical.
16. Funny People
Few movies have depicted the life of a struggling, up and coming standup comic this accurately. The anguish of bombing on stage and the feeling that no one besides you cares if you succeed or not is so painfully accurate. Seth Rogen, having once been a struggling comic himself, plays it perfectly. It elevates the movie with a sense of reality. And it was Adam Sandler’s best performance in years, as he parodies himself and plays dramatic scenes with serious gravitas and grace. The problem is that it is way too long. This is a comedy movie and it’s two and a half hours long. It’s a movie about the standup comedy scene and it’s also a movie about a guy with cancer who reassesses his life on death’s door. Maybe Apatow should’ve picked just one and kept it to a manageable length.
15. Get Him to the Greek
Forgetting Sarah Marshall was Jason Segel’s movie, but one of the best supporting players was Russell Brand as the lackadaisical, seemingly down to Earth rock star Aldous Snow, and his funniest moments came from his hilarious chemistry with the wannabe musician played by Jonah Hill. This spin-off wisely cast Hill in a different role, as a record label executive who is tasked with getting Aldous through the promotional tour for his comeback gig and coming out alive on the other side. A lot of modern comedies fail in their attempts to portray debauched antics, but this movie is hilarious from start to finish.
14. Anchorman 2: The Legend Continues
Sequels are tricky to do in comedy, especially when the original felt so fresh and original when it first came out. How do you emulate that and keep the same feel and still be just as fresh and funny and still give the fans what they loved about the first one and still give them something new? It’s full of paradoxes! It’s basically impossible to pull off. But to be fair to Will Ferrell and Adam McKay, they didn’t betray any of their characters, they wrote a story that felt very fresh and original, they didn’t put in too many callbacks (but they did put in some), and it is filled with memorable jokes and gags (for example, “I’M BLIND!!!”). It’s as good as a comedy sequel can be, but sadly, that’s not as good as original comedy can be.
13. Walk Hard: The Dewey Cox Story
This fake music biopic starring John C. Reilly as a composite of Johnny Cash, Bob Dylan, Roy Orbison, Ray Charles, and Jim Morrison is spot on as a parody of how such movies sensationalize their subjects and dramatize even the slightest changes in their lives. Every biopic cliché is lampooned here – it’s brilliant. It’s a shame that this movie didn’t make a big splash at the box office, because it’s hilarious. The scene where Tim Meadows tries to convince Dewey not to smoke weed (“You don’t want no part of this shit!”) is a highlight.
Standup comics don’t always make for great screenwriters, but if they respect story structure and put the care into their characters and where their plot is going and consider how the jokes are going to fit in instead of just cramming them in, then they can write some hilarious and successful scripts. Amy Schumer is a prime example of this, as she took the traditional setup of a romantic comedy and swapped out the stereotype of the dainty, ditzy girl for her particularly raucous personality. Instead of telling the story of a guy who sleeps around and screws up his relationships and then meets the one, she told the story of a girl who sleeps around and screws up her relationships and then meets the one. It sounds obvious, but no one had ever done this before – and it was pretty awesome.
11. Popstar: Never Stop Never Stopping
Ever since This is Spinal Tap blazed the trail, it’s been pretty much impossible for comedy filmmakers to make their own music mockumentary. But with a rapid fire gag rate and seemingly endless inspiration, the Lonely Island guys managed to give Spinal Tap a run for their money as they satirized the artistic limitations, psychotic fan followings, lavish lifestyles, and absurd wardrobe choices of such pop stars as Justin Bieber, Lady Gaga, and Taylor Swift. If you like the Lonely Island sense of humor, then you’ll love this movie. A lot.
10. The Big Sick
Real life married couple Kumail Nanjiani and Emily V. Gordon based this movie on the story of how they fell in love. The problem with a lot of romantic comedies is that they feel totally manufactured. They follow the same old Hollywood formula: boy meets girl, yada yada yada. None of them feel real or personal or inspired. So, it was a refreshing change of pace for a screenwriting duo to use their own love story as the basis for a romcom script. And it’s not just a story of two privileged white people falling in love either – Kumail’s Pakistani culture gets in the way. Plus, the structure is interesting, because Emily is in a coma for the whole second act where the guy and the girl are supposed to fall in love, so the guy is the only one awake for that part, and then when she wakes up, they’re back to square one. It’s very interesting. That Oscar nomination was highly deserved.
9. Talladega Nights: The Ballad of Ricky Bobby
Will Ferrell and Adam McKay’s follow up to Anchorman could have suffered from second album syndrome, but to their credit, their send-up of NASCAR culture, replete with product placement and idiocy and American nationalism, was even bigger and bolder than their big screen debut. Scenes like when Ricky thinks he’s disabled and stabs himself in the leg or when Ricky tells Girard to break his arm so he doesn’t have to admit to liking crepes are among the funniest ever filmed. It’s a satirical movie that doesn’t let the satire take over from plot and character development. Beautiful stuff.
8. Knocked Up
Judd Apatow knows that if you want your movie to resonate with audiences on a deeper level than typical Hollywood tripe, then you have to access painful personal experiences and put them on the screen. You know that scene where Alison kicks Ben out of the car on the way to a scan when she gets upset with him? That really happened! The beauty of the movie is that Ben and Alison represent Apatow and his wife Leslie Mann when they were pregnant with their first child, while Debbie and Pete represent them as they are now – married with two kids. Is there any more personal a movie than one where the director has his younger self meet his older self in order to get advice? It’s fantastic.
7. Forgetting Sarah Marshall
You wouldn’t think there would be a market for romantic comedies aimed at men, but that’s just because no one had ever tried it before. Jason Segel wrote a romantic comedy for a male audience as his first ever feature length screenplay and it turned out to be a huge success. His script captures the struggles of toxic relationships and the heartbreaks of ending a long term relationship perfectly. As a study of relationships, it hits the nail right on the head. And it’s also damn hilarious, especially with brilliant supporting turns from Paul Rudd, Jonah Hill, and Russell Brand, all of whom relish every scene in which they get to play their absurd characters.
6. Pineapple Express
A lot of stoner comedies, purely due to the fact that they’re made by stoners, are not particularly great movies. If you watch a movie by Cheech and Chong when you’re not baked, it’s not really funny and it’s certainly not a well made motion picture. But Pineapple Express is. Seth Rogen and James Franco are paired perfectly (with the interesting casting decision of having the comedic actor play the straight man and the dramatic actor play the wacky doofus paying off in spades), David Gordon Green directs the film deftly, and Tim Orr’s cinematography is gorgeous. Plus, the gags and the jokes and even the slapstick moments work wonderfully. It’s a hilarious movie.
5. Step Brothers
With this movie, Will Ferrell, Adam McKay, and John C. Reilly set out to make the silliest, weirdest, and most absurd little comedy that they could. They didn’t even expect it to turn a profit. The fact that it ended up being one of their highest grossing works is a testament to how successful comedy can be when you take off the commercialist constraints and just let loose. It is seriously one of the funniest movies of all time – a few structuring issues aside, you can hardly fault it. It’s one of those comedies that stands endless rewatching and never ceases to get a laugh. Every line is written and then delivered to perfection.
This was not just a funny movie – it was a movie that portrayed love and friendship and relationships in a raw and frank way. It felt so realistic. The characters were not the kind of women who are written by men to be the misogynistic fantasies that they want them to be – these were real women. The secret? The script was written by women. Who saw that coming? Women know how to write women! Well, Judd Apatow and Paul Feig saw that coming and they made a romantic comedy that not only won over critics, audiences, and the Academy, but also changed the comedy landscape for women. It paved the way for a bunch of female led comedies.
3. The 40 Year Old Virgin
This movie was the trailblazer for the R rated comedy boom of the mid to late 2000s. Its mixture of scripted and improvised humor and its telling of an ultimately sweet story through the use of adult humor were revolutionary for its time – and still remain one of the finest examples of that kind of comedy filmmaking. The ensemble cast of actors – Steve Carell, Seth Rogen, Paul Rudd, and Romany Malco – are all matched hilariously with one another and have the improvisational skills required to pull off the kind of experimental shooting style that Judd Apatow used with his directorial debut.
Seth Rogen and Evan Goldberg worked on their first feature length screenplay – based on their own high school experience in Canada – for over a decade before they got it into the hands of Judd Apatow, who gave it the greenlight and got it into production. So, over the course of all those years, they revised and refined every joke and story beat and character until they were completely perfect and rounded out. It is virtually unparalleled as a piece of comedy writing. Of course, none of this would matter if it wasn’t cast right, but thanks to the easy chemistry of Jonah Hill and Michael Cera, Rogen and Goldberg’s words translated beautifully to the screen.
1. Anchorman: The Legend of Ron Burgundy
It is no exaggeration to say that Anchorman ranks alongside the likes of Airplane! and Blazing Saddles as one of the finest and funniest comedy movies ever made. From Ron’s conversations with his dog Baxter to his TV broadcast warm-up phrases to the news team showdown, the whole script is constructed to give Will Ferrell and Adam McKay ample opportunities to cram in jokes (or hilarious, random, absurdist non-sequiturs) wherever they think of them. The actors were allowed room for improvisation and you can never guess where the plot is going. What results is a comedy masterpiece that has inspired a generation of comedy writers and performers.