Funny person: 10 of Judd Apatow’s best films

The acclaimed filmmaker's latest movie, 'The King Of Staten Island', is available to rent at home on June 12

In partnership with Universal Pictures

Pick a great American comedy from the last 20 years and there’s a pretty good chance that Judd Apatow had something to do with it. As director, writer and producer he helped a whole new wave of stand-ups hit the mainstream in the mid-’00s – mixing wholesome family feels with ballsy stoner humour. Leaving his TV work aside, it’s time to round up the king of comedy’s 10 best movies – just in time for his latest, The King Of Staten Island, available to rent at home on June 12.

‘The Cable Guy’ (1996) – producer

One of the first films Apatow ever produced was also his darkest – helping Ben Stiller make a nasty little comedy horror about a socially awkward TV technician who starts stalking the first guy who’s nice to him. Slightly overpowered by Jim Carrey’s lisping, leering, terminally creepy performance, it still stands as a sharp and subversive take on the bromance – a genre that hadn’t even been invented back in 1996.

Funniest line: “You know what the trouble about real life is? There’s no danger music.”

‘Pineapple Express’ (2008) – producer

Back in 2008, director David Gordon Green was only known for melancholy indie dramas like George Washington and Snow Angels. And then Judd Apatow came along and convinced him to make the mother of all stoner comedies instead. Everything spirals out of control for Seth Rogen, James Franco and Danny McBride as the film jumps from sleepy hotbox haze to full on action – complete with high-speed chases, gun fights and extreme violence. It’s basically the arcade game version of Superbad.

Funniest line: “Couscous: the food so nice they named it twice.”

‘The Big Sick’ (2017) – producer

Classic story: boy meets girl, girl breaks up with boy, girl goes into a coma, boy sticks around anyway – hanging out with her parents, sitting with her in hospital, acting like they’re still in a relationship. It doesn’t sound like a bundle of chuckles, but The Big Sick manages to stay hilarious as well as heart-breaking. What’s more, it gave a much-needed platform to Kumail Nanjiani – bringing Pakistani-American comedy into the mainstream.

Funniest line: “Your driver will be ready as soon as he puts on pants.”

‘Forgetting Sarah Marshall’ (2008) – producer

Get Him To The Greek is great, but it plays much broader than the far better film it spun-off from – a textbook example of how not to deal with a bad break-up, and one of the funniest movies of the ’00s. Jason Segel is perfect as the sad-sack pining for his ex (Kristen Bell), and he’s almost upstaged by Russell Brand until he gets his muppets out for a one-man Dracula rock opera. Another example of an Apatow movie flipping the romcom on its head, this guy-driven weepie deserved a sequel because it did things other comedies didn’t think of doing (also because Brand was too good a side character not to give a whole movie to).

Funniest line: “Just one week with Sarah was like going on holiday with… I don’t want to say Hitler… but Goebbels, maybe”.

‘Superbad’ (2007) – producer

The one that started it all – written by Evan Goldberg and Seth Rogen whilst they were still at school, Superbad launched a dozen careers, reinvented the teen high school movie and kickstarted a new Hollywood comedy club led by Judd Apatow. It also gave us “McLovin”, which is still the best name to put on any fake ID. Box fresh back in 2007, it’s way better than any film written by two kids has any right to be – rude, nerdy, smart and surprisingly sensitive.

Funniest line: “You know how many foods are shaped like dicks? The best kinds.”

‘The 40-Year-Old Virgin’ (2005) – director

No one balances comedy and sadness better than Steve Carell (just watch The Office), and no one directs it better than Judd Apatow. Everyone remembers the chest-waxing scene but the physical comedy isn’t half as good, or even as funny, as the fine-lined character study going on beneath all that curly hair. Hiding its hard-felt emotions behind crudeness, Apatow’s first film is much more mature than it sometimes sounds – and Carell’s honest, heartfelt performance helps him make the sweetest sex comedy of his career.

Funniest line: “Do you have protection?” “I don’t like guns”

‘Knocked Up’ (2007) – director

Seth Rogen wrote Superbad when he was teenager, but by the time the film eventually got made he was already old enough to have kids of his own – making him the perfect choice for collaborating with Apatow again on the definitive pregnancy comedy in the same year. Knocked Up took a lot of flack at the time for being sexist, but the crudeness of Rogen’s hilariously under-prepared new dad is kind of the whole point: what happens when a man-child suddenly has to grow up? Judd Apatow seems to have been asking the same question ever since.

Funniest line: “Your face looks like Robin Williams’ knuckles”

Funny People (2009) – director

Deemed over-long by some, Funny People underperformed at the box office and isn’t seen as one of Apatow’s most-popular titles – but of all the films Apatow has directed none feel quite as personal or half as unique. A lifelong comedy geek (read his fantastic collection of stand-up interviews, Sick In The Head, to see just how much), Apatow spoke from his heart with Funny People – giving us a sprawling ode to comedy, comedians, his family, all his friends and his one true hero, James L. Brooks. It might be two and a half hours long, but it’s well worth spending the time with if you really want to get inside Apatow’s head.

Funniest line: “When my grandfather died, there was one candle next to his bed and it started flickering. We all thought it was him going to Heaven.”

“You don’t pass through fire to get to Heaven. I think he went to Hell.”

‘Anchorman: The Legend Of Ron Burgundy’ (2004) – producer

The sequel might have been less-appreciated and all the old Brick quotes, Brian memes and Ron Halloween outfits might have stopped being funny years ago, but then and now there simply hasn’t been a weirder, sillier, funnier comedy made in a generation. Putting a dozen great comedians in the same studio and letting them run wild, Apatow’s great genius as a producer is in picking the right talent and trusting them enough to do their own thing. If Apatow ever has a tombstone, it will read “he was kind of a big deal”.

Funniest line: “I’m in a glass case of emotion!”

‘The King Of Staten Island’ (2020) – director

Judd has a knack for finding huge talents just before they hit the big time. In 2005, he kickstarted the career of Steve Carell with The 40-Year-Old-Virgin, and three years later, the director helped give Seth Rogen his biggest leading role yet in Knocked Up. Apatow’s latest youngster, Pete Davidson, is all kinds of funny in The King Of Staten Island. Well-known for his work on Saturday Night Live, Davidson plays Scott, who has been struggling to cope with the death of his firefighter dad. He spends his days smoking weed and dreams of becoming a tattoo artist, but eventually, events conspire to get him off the couch and into the big wide world of New York City.

Funniest line: “‘Knock knock.’ ‘Who’s there?’ ‘Not your dad!’”

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