The Films of Judd Apatow – Ranked!

 (A version of this article originally appeared on kernelnow.com / mynewslike.com)

In the fifteen years since his big-screen debut, director Judd Apatow’s name has become synonymous with modern comedy, arguably crossing over to become one of the most familiar names in all of cinema. Now,on the cusp of the release of his latest film The King of Staten Island, it seems like a good time to rank the famed film-maker’s back catalogue.

Of course, his name is well-known for so many reasons more than the five films we’re about to look at below, having turned his hand as a producer, screenwriter and even documentarian. However, for the purposes of this article, we’ll be looking at the feature films that, like his upcoming video-on-demand outing, are listed as having been directed by Apatow – both to keep things at a manageable length, and to give all films not named Superbad a fighting chance at the top spot.

 5. This is 40 (2013)

Maude and Iris (left), Judd Apatow’s children, have appeared in three of the director’s films
(source: CBR)

Unless they’re married to another genre, like Beverly Hills Cop or Austin Powers, comedy films rarely venture into sequel territory. This is 40, the “sort-of sequel” to the Judd Apatow’s highest-grossing film Knocked Up, may be a case study into why.

The real problem is in the world-building – or perhaps more accurately, the world-borrowing. There’s a loose handful of returning characters, but Jason Segel’s self-titled portrayal suffers from his more direct involvement, and you’d be forgiven for forgetting that Jodi (Charlyne Yi) is a returnee at all; this, along with the existence of the original’s odd couple Ben and Alison as mere passing mentions, reinforces the idea that the real charm of this world has already been fully explored. Melissa McCarthy is inevitably hilarious in her extended cameo as an enraged mom, but otherwise there’s much less charisma present as the film struggles to escape from the ghosts of Knocked Up past.

The performance of the two main actors is the film’s biggest strength. Whilst her range has been on display throughout her appearances in Apatow’s previous films, Leslie Mann – the director’s real-life spouse – truly exerts herself in the lead role here, and Paul Rudd is as effortlessly appealing as ever. The problem is that the bickering duo existed as a warning in the previous film, a “worst case scenario” warning for the central plot, and only stole scenes in the moments where they were separated. There were arguably more engrossing dynamics in Knocked Up than the married couple airing their dirty laundry, and spending the best part of another two hours in their bad-tempered company leaves this film in desperate need of one of Apatow’s signature, truly likeable double acts.

Of course, this isn’t a completely unwatchable film; you just can’t help but wonder if this storyline is burdened by the baggage and expectations of its predecessor. Perhaps the film would have been better served with a completely original cast of characters but, whatever the case, This is 40 represented a rare misstep from the now well-established film-maker.

4. Funny People (2009)

Adam Sandler (left) and Apatow have been firm friends since their earliest days in comedy
(source: IndieWire)

It may seem a little ironic that Funny People is the Judd Apatow film with the least amount of laughs. However, that’s not due to any failings in writing, but more because this is the most serious of all of Apatow’s films.

The title does not refer to  the usual Apatowian “people being funny”, but instead the actual people whose job it is to be funny – specifically, a floundering and depressed comedian George Simmons (Adam Sandler) who’s diagnosed with a terminal illness and given just an 8% chance of survival. Cynical over not just his career but his entire existence, George is like the record label owners and career journalists in Apatow’s other films who show that having a dream job does not guarantee a dream life.

Viewers may be more familiar with Punch-Drunk Love or Uncut Gems as examples of Sandler’s dramatic abilities but this particular portrayal may be the best of them all, as Apatow uses both Sandler’s well-known celebrity and their real-life friendship to create a character that blurs the line with reality. This is a complicated story which first shows the “serious illness” narrative can be more than just melodrama, and then asks whether or not life-changing circumstances automatically lead to redemption. It’s a very personal and endlessly probing film, as even “good guy” Ira (Seth Rogen) shows deep flaws with the impossible standards he holds for both his hero George and a prospective girlfriend.

Unfortunately, the demands of a “comedy director” like Apatow work against him; this film does offer laughs but they’re submerged in questions arguably too lofty for a comedy, and a 146 minute runtime which even by Apatow’s lengthy standards is a huge ask. Whilst he should not be criticized for an honest and original approach to a serious subject matter, the fact remains that, for all its nuance, Funny People sits as the least accessible of all its director’s works.

3. The 40-Year-Old Virgin (2005)

2005 was a big year for Steve Carell, making his debut as both a feature film lead here and in NBC’s The Office
(source: Bustle)

By 2005 and as a result of shows like Freaks and Geeks, Judd Apatow and his “Frat Pack” friends already had close to a decade and a half’s experience in comedy. Yet in his big-screen debut, The 40-Year- Old Virgin, the newly-crowned film director was still clearly exploring his own unique style, resulting in a movie which is both one of his best and his most unrecognizable.

Whilst many of the stars of this film – such as Paul Rudd and Seth Rogen – would appear in future Apatow productions, their performances here are very different to their later, more charming roles. Taking advantage of the largely-improvised script to mimic the raunchy comedy icons they grew up watching, the supporting characters here deliver off-hand jokes about sex and sexuality that, in retrospect, range from regrettable to unforgivable. The result is a movie which often feels as dated now as National Lampoon or Animal House would have to mid-2000s audiences then.

The film is rescued at its heart by Andy, played by Apatow’s co-writer on the film, Steve Carell. The film’s title makes it obvious where Andy’s journey will take him, and whilst there are inevitable jokes about his inexperience and loneliness he’s never presented as anything less than sincere. Andy has the unique ability to turn others into better people just by being in their company as he goes on a journey of genuine self-help, showing that being a virgin is just as honorable as the quest to find (and make) love with “hot grandma” Trish (Catherine Keener, in an entirely underrated performance).

With his name established in the wake of this middle-aged American Pie, Apatow would be able to tone down the R-rated guise (and guys) in his future projects. However, he would take the earnesty of his protagonist here and develop it into a much wider cast of relatable characters. At the time, Entertainment Weekly said that Andy represents “a credible human being” – surely the same can be said for most of Apatow’s future creations, showing just how essential this often-crude film was in establishing the director’s career.

2. Trainwreck (2015)

Written by Amy Schumer, Trainwreck was Apatow’s most sexually-charged film in ten years
(source: New York Times)

It’s been five years since Judd Apatow last directed a feature film, and his last outing was an outlier in that he neither wrote it himself, nor cast any of his usual suspects. 2015’s Trainwreck, starring Amy Schumer, has the hallmarks of a classic Apatow script, featuring a character at an emotional and personal crossroads in their life – it was just written by someone else.

That someone else is the provocative comedian Amy Schumer, star of her own edgy Comedy Central sketch show. That controversial side is largely absent from this film, however; Schumer does use her platform to make pointed statements, but they’re not quite as boisterous as usual, this project offering a greater emphasis on storytelling than previously seen of her brand. This is helped in no small part by the presence of her director and his skill at creating grounded human characters, with Apatow surely having a much heavier influence on the story than his lack of writing credit suggests.

Trainwreck subverts the romcom genre, particularly in the gender roles of Amy and her boyfriend Dr. Aaron Conners (Bill Hader). The film isn’t afraid to frankly discuss sex, nor to parody either gender’s traditionally agreed-upon corner of society. It’s in these send-ups that the classic Apatow scene-stealing guest stars are to be found: Tilda Swinton is delightfully unrecognizable as a depraved mask of herself in magazine executive Dianna, and then there are the cameoing athletes. John Cena’s turn as Amy’s bilingual “ice sculpture” of a lover set him on the road to movie stardom proper, and LeBron James’s send-up of the “best friend” romcom stereotype is nothing short of a revelation. These knowing spoofs come off much better than the film’s conventional comedic skits, which regularly feel as more than a little far-fetched.

Trainwreck maintains the conscience of a Judd Apatow film, whilst also feeling like an extended Saturday Night Live piece, which isn’t to say the funnies are throwaway but instead that all involved are in on the joke. There may not be much to convert the critics of any involved, but this is a committed and fresh spin on not just the romcom, but the idea of a “Film by Judd Apatow”.

1. Knocked Up (2007)

Knocked Up announced the arrival of many new comedy stars, not least its leadSeth Rogen (left)
(source: tvandmovienews.com)

There have been a number of recurring themes in the films we’ve looked at so far: bona fide comedy superstars, superb supporting casts, odd couples, and characters in over their head. The successful fusion of these elements can all be traced back to one film. Released to the tune of $219 million worldwide, Knocked Up serves as the prototype for what makes an Apatow film – but unlike most big-screen blueprints, it never bores on repeat viewings.

Blending life-changing circumstances similar to Funny People with the bawdy slapstick of The 40-Year-Old Virgin is no mean feat, but here Apatow manages it. Where Trainwreck later took a heavy dash of sports to increase the gender appeal of a romcom, this film takes the crisis of an unplanned pregnancy to more broadly relate its “late night comedy” schtick; the film is tender enough to explore the worries of starting a family, but risqué enough that Anne Hathaway stepped away from the lead role. Not a single sequence or laugh is wasted, each pushing Ben (Seth Rogen) and Alison (Katherine Heigl) further down their anxious path. Their worries and relationship/s are authentic, and every single spin-off scene with a sister or housemate gives the couple food for thought for their awkward meetings in restaurants and baby clinics.

The sense of identity extends backwards too, as Ben and his housemates feel like evolutions of the Freaks and Geeks cast, Apatow’s two-season sitcom from the early 2000s. This is the moment where this “Frat Pack” was established as more than just “The Next Big Thing” – just look at Rogen’s blockbuster role in The Lion King or Jonah Hill’s Academy Award nominations for evidence of this film’s lasting impact. When you think of these names or their cohorts like Paul Rudd and Jason Segel, then scenes from this movie immediately spring to mind.

The film does establish the lengthy runtime common in all Apatow features, but it’s never a chore to spend time in the company of these sincere, “credible human beings”. All too often, comedies wow upon their release but fail to hold up in the years after their release; however, thirteen years later, Knocked Up has earned its reputation as a comedy classic.