Over the last 20 years, the writer-director duo of Phil Lord & Christopher Miller have created some of the most beloved comedies of a generation. From humble beginnings, they've climbed the ranks from television animation, to PG adventures, to R-rated comedies, to franchise-expanding tentpole projects, and have even won an Academy Award. Though they've shown no signs of slowing down, their filmography offers as many laughs upon ranking their four features as each of their directorial efforts did the first time around.

Lord and Miller met at Dartmouth, where they discovered that they'd each grown up making short films and shared an interest in filmmaking. A profile on Miller in the college newspaper caught then-Disney-CEO Michael Eisner's eye, and upon being offered a meeting, he insisted Lord be brought along. The pair took a development deal with Walt Disney Television Animation and their careers began.

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Since then, they've worked on all manner of projects, from the short-lived Clone High series bought by MTV, to their first feature, an adaptation of the children's book Cloudy with a Chance of Meatballs. They parlayed their success into helming the Jump Street reboots, while also working in TV for shows like How I Met Your Mother, Brooklyn Nine-Nine, and The Last Man on Earth. They earned themselves a big-budget franchise project, working extensively on the Star Wars standalone prequel Solo: A Star Wars Story before leaving due to "creative differences." For their role in producing Spider-Man: Into the Spider-Verse, the duo received the Academy Award for Best Animated Feature, beating out industry stalwart Pixar's Incredibles 2. Each of the four feature films they've directed offers different flavors of their signature witty and reflexive approach to comedy, and they've only honed their craft over time. Let's split some hairs and rank some of the most clever comedies of the last decade.

#4: Cloudy with a Chance of Meatballs

Flint smiling with a hamburger in his hand in Cloudy with a Chance of Meatballs

Their first time in the directors' chairs may be last on this list, but Cloudy with a Chance of Meatballs is by no means a bad movie. Based on concepts from the children's book of the same name, the film's story explores a small island nation whose humdrum sardine economy has poisoned the quality of life, when one day the town's outcast inventor builds a machine to create weather that rains food from the sky. The movie boasts familiar-yet-delightful character designs, zany performances from Bill Hader, and the offbeat, genre-reflexive jokes that fans would come to expect from future Lord & Miller properties. The satirically cynical side-character prototypes, visual tropes and gags, and witty dialogue references find their origin here.

Lord and Miller first wrote the film in 2003, but were fired, then rehired, then nearly fired again during a tumultuous development process. In building the story, which required significant bulking-up from the original IP, they learned the value of creative collaboration and a film's emotional core. The movie made back over double its budget at the box office, is certified fresh on Rotten Tomatoes, and gave the duo the chops and credibility to jump into future projects.

#3: 21 Jump Street

Schmidt and Jenko wearing tuxedos and pointing their guns at someone

Riding the success of Cloudy with a Chance of Meatballs, the duo snagged the directing job on Jonah Hill and Michael Bacall's 21 Jump Street script. In it, Jonah Hill and Channing Tatum are undercover cops sent back to high school to, according to Ice Cube, "infiltrate the dealer, find the supplier." The film makes ample use of the reflexivity that permeated Meatballs, but with the freedom to take things into R-rated territory. From criticizing Hughesian high school tropes, to examining action flick tropes (see: "I really thought that was gonna explode..."), to cleverly referencing story structure at the conclusion of the film's second act, Lord and Miller here begin codifying their brand of comedy.

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Critics and audiences embraced 21 Jump Street, praising the chemistry between the two leads, the clever writing, and the takedown of genre elements, all leveraged to great comedic effect. The film earned nearly four times its budget and spawned a sequel.

#2: 22 Jump Street

Jonah Hill & Channing Tatum in 22 Jump Street

Speaking of that sequel, 22 Jump Street edges out its predecessor for a simple reason: everything that makes 21 great, 22 does better. Hill and Tatum are back, the writing continues to flex its wit, and the genre elements are as starkly undressed as ever. It relishes in its status as a sequel. Instead of shying away from typical sequel criticisms—it retreads the plot of the first movie, it lacks what made the first special, etc.—it steers into these head-on. In fact, the sequel element plays squarely into Lord and Miller's comedic hand, allowing them to wring even more reflexive jokes out of the premise. It's a laugh-a-minute college/buddy-cop comedy that earns its reputation as one of the better sequels in recent memory.

The film made over $300M at the box office against a $50M budget and endeared itself to critics in a similar manner to the first film. The protracted end credits sequence almost begs for the countless Jump Street sequels it promises, but none have thus far materialized. At any rate, Lord and Miller's attention was drawn elsewhere after wrapping 22 Jump Street, as they briefly forayed into the Star Wars universe before entering a more producer-only phase of their careers. But months before the release of 22 Jump Street, the best film they've directed thus far came out.

#1: The Lego Movie

At first glance, The Lego Movie represents a major wrong with Hollywood. After enduring pointless sequels and franchises nobody asked for, it seemed the market was saturated with soulless, uninventive, purely commercial movies that felt more like products aimed to punch up a bottom line rather than enjoyable moviegoing experiences. Audiences taking this attitude into The Lego Movie found themselves floored with just how wrong they were. The film satirizes the hero's journey with all the playful wit of Lord and Miller's other films, but they took their emotional core lesson from Meatballs and turned it up to 11 with arguably Will Ferrell's most tearjerking scene in a lengthy career. Writing and talent aside (a star-studded voice cast give pitch-perfect performances), the animation quality is remarkably adept, keying in on macro artifacts that lend the film an authenticity, as if everything shown really were comprised of the very LEGO bricks that live in the home of most every kid in America.

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Despite audience and critical consensus that this film was a hit, it was infamously snubbed at the Academy Awards, where it was not nominated for Best Animated Feature (but did receive a nomination for Best Original Song). The film tapped into viewers' desire to feel special, a prominent struggle of a generation growing up and grappling with the realities of life. It simultaneously mined all the creativity and boundless potential for which its "Toy of the Century" inspiration is so often celebrated. It spawned a sequel and spinoff; neither was directed by Lord and Miller but both drew heavily on their influence. While it's daunting to be sure, there's every reason Phil Lord and Christopher Miller have more home runs like The Lego Movie ahead of them in what's been, and will hopefully continue to be, a fruitful career. Here's to hoping they keep making great movies.

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