Judd Apatow’s Outrageous Comedies Ranked

by : Cameron Frew on : 06 Dec 2020 17:43
Universal Pictures

It’s Judd Apatow’s 53rd birthday. To celebrate, we’ve ranked his funniest comedies. 

In the public eye, his films are likely known more for his trademark roster of stars: Seth Rogen, Paul Rudd, Adam Sandler, Jason Segel, Leslie Mann, Jonah Hill, Bill Hader, etc.


However, the writer-director has rubberstamped some really terrific films over the past 20 years, like Anchorman, Superbad, Forgetting Sarah Marshall, Step Brothers and Popstar: Never Stop Never Stopping. He’s arguably the most influential figure in modern comedy, particularly post-2005.

Leslie Mann Judd ApatowPA Images

For this list, we’re avoiding his bountiful producer credits for movies solely directed by Apatow. We’ve also left off his two documentaries – May It Last: A Portrait Of The Avett Brothers and The Zen Diaries of Garry Shandling – as we’re only ranking the comedies.

6. This is 40

This is 40Universal Pictures

It’s the easy target of Apatow’s filmography. A quasi-sequel to Knocked Up, it focuses directly on Leslie Mann and Paul Rudd’s (un)happily married couple in domestic bliss/limbo/hell. The problems: its plot is indiscernible, more like an episode of a sitcom that’s way, way too overblown. That ties into its second issue: the 134-minute runtime, a stretch even for those who find its comedy relatable.

That said, there’s smiles to be had. Laughs do pop up, often hearty over giggles thanks to the lead couple’s chemistry, and there’s a real warmth beneath its gluttony of, well, nothingness.

5. The King of Staten Island

The King of Staten IslandUniversal Pictures

The scales of Apatow’s fondness of drama tip towards the former in The King of Staten Island, this year’s quietly released Pete Davidson vehicle. It’s said be a semi-biographical account of his life, co-written by the SNL star, having lost his father in the 9/11 attacks and later struggling with mental health issues.

While equipped with another indulgent runtime, there’s elevated, mature storytelling here. In an earlier interview, the filmmaker said it ‘speaks to grief and trauma, even though it’s a comedy, and that relates to what we are all experiencing. Unlike how I usually work, I wasn’t obsessed with making every line funny’.

4. Funny People

Adam Sandler Judd ApatowUniversal Pictures

Uncut Gems was a blistering showcase of Adam Sandler’s acting prowess. Years before, he attuned his loudmouth comic sensibilities and nuance for Funny People, Apatow’s meta-text about the throes of selfish fame. It’s stand-up dramedy at its finest.

Co-starring alongside Seth Rogen and Leslie Mann, it pits Sandler against a life-ticking illness and his indulgent lifestyle coming home to roost. Again, the runtime is far too long, but the bromance is leisurely and sweet – richer due to the director and Sandman being former roommates – with raunchy humour spicing up otherwise serious reflections on life itself.

3. Trainwreck

TrainwreckUniversal Pictures

First, a rule of thumb: casting Bill Hader automatically makes any movie better by a considerable margin. In Trainwreck, he’s the supporting foil to Amy Schumer’s titular waster, coasting through a man-to-man life of work, drink, crash and repeat on the back of her dad’s… problematic childhood advice about monogamy.

It’s the star’s script that punches it into spikier, fresher territory, still surrendering to the rom-com clichés under a fading guise. Hell, I’m willing to admit it even makes me a bit weepy when that Uptown Girl cue comes in. But if you need one reason to watch, it’s John Cena’s hulking, homoerotic, disaster artist of dirty talk. He’ll give you the protein.

2. Knocked Up

Knocked UpUniversal Pictures

In 2007, Seth Rogen became a Hollywood leading man, if an unconventional one. Knocked Up answers the question: what if a layabout stoner living off injury compensation and dabbling in a ripoff celebrity porn website gets an accomplished L.A reporter pregnant from a one-night stand?

Apatow’s pairing of Rogen and Katherine Heigl was a masterstroke, as is his writing; it’s a frank farce, unafraid to laugh at the touchier aspects of relationships, growing up and welcoming a new life into the world. It was a certifiable turning point not just for romantic comedies, but comedy at the movies – the new generation of jokers were here.

1. The 40-Year-Old Virgin

40-YEAR-OLD VirginUniversal Pictures

Heavyweights was his official start, but The 40-Year-Old Virgin was the dawn of Apatow’s reign. Even 15 years later, it’s his most hilarious, perceptive work that’s far wiser and kinder than one likely presumes.

Everything and everyone in this movie is funny. The waxing scene alone is enough to achieve legendary status, but the quotes are also timeless; from Paul Rudd’s ‘If I hear Yah Mo B There one more time, I’m going to Yah Mo burn this place to the ground’ to Steve Carrell’s ‘bag of sand’ anecdote.

Seth Rogen, Rudd and Romany Malco’s improv is infectious, even when it’s horrible (the Tijuana horse). Yet, beneath its R-rated raunchiness and jabs, the titular virgin never feels like the true butt of the joke – it’s those around him who place so much stock in what he’s afraid of. The best comic heroes are those we can laugh at, but root for all the same.

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Cameron Frew

After graduating from Glasgow Caledonian University with an NCTJ and BJTC-accredited Multimedia Journalism degree, Cameron ventured into the world of print journalism at The National, while also working as a freelance film journalist on the side, becoming an accredited Rotten Tomatoes critic in the process. He's now left his Scottish homelands and taken up residence at UNILAD as a journalist.

Topics: Featured, comedy, Film and TV