With the 2022 awards season underway, there's a lot of talk about when it comes to acclaimed director Paul Thomas Anderson's latest film, Licorice Pizza. The film is chock full of many key characteristics of Anderson's work: the Los Angeles setting, a wildly charming ensemble cast, and a heartwarming, albeit slightly unsettling, story. It has also, like much of his other work, proved divisive among critics and audiences alike.

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Like any respected auteur in filmmaking, the ranking of Anderson's filmography is constantly debated every time the director puts out a new film. With all the buzz surrounding Licorice Pizza lately, it would be worthwhile to take a look at Anderson's feature-length work so far and see how his new project stacks up compared to his older masterpieces.

9 Hard Eight

John C. Reilly and Samuel L. Jackson sitting in a bar in Hard Eight

Hard Eight was Paul Thomas Anderson's directorial debut in 1996, inspired by the director's own short film three years earlier called Cigarettes & Coffee. Like the short film, it stars Philip Baker Hall. Here, Hall plays a professional gambler who takes a homeless man, played by John C. Reilly, under his wing. Hall and Reilly would later go on to star in Anderson's later films Boogie Nights and Magnolia, alongside Philip Seymour Hoffman, who also appears in this film.

Like his future work, Hard Eight is a thrilling crime movie that thrusts its difficult-to-like characters into intense scenarios. It clearly showed that Anderson was already a master at work, though it lacks some of the ambition and complexity of what would come next.

8 Phantom Thread

Daniel Day-Lewis making a dress for Vicky Krieps in Phantom Thread

Released in 2017, Phantom Thread was an awards darling the year it came out, mostly due to a committed performance by Daniel Day-Lewis in his second outing with Paul Thomas Anderson. The film follows Day-Lewis as a dressmaker in London and the complex, romantic dynamic he develops with a waitress played by Vicky Krieps.

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Phantom Thread is the most different from any film Anderson's ever done, and was noted by critics for its surprising level of humor and romance. It's certainly not Anderson's best work with the notorious method actor, but it remains an entertaining watch nonetheless.

7 Inherent Vice

Joaquin Phoenix and Katherine Waterston leaning over to listen to a phone together in Inherent Vice

This was Paul Thomas Anderson's second film with Joaquin Phoenix, who plays a drug-addicted private investigator in Los Angeles in 1970. The film, which was released in 2014, is quintessential Anderson: riddled with comedy, a provocative story, and at times frustrating to watch. Of course, it's hard to expect anything less when the supporting cast includes Martin Short, Owen Wilson, and Maya Rudolph.

Based on a novel by Thomas Pynchon, the film later went on to get Anderson an Oscar nomination for Best Adapted Screenplay. However, like many book-to-film adaptations, its messiness can hinder it from standing up to some of Anderson's more iconic work.

6 Magnolia

A close-up of Tom Cruise on stage in Magnolia

As the follow-up to his breakthrough film Boogie Nights, Paul Thomas Anderson took the word "ambition" to a whole new level. Coming in at over three hours long (it's seven minutes longer than Avengers: Endgame), the film follows separate yet connected characters who all live in the San Fernando Valley. The ensemble cast includes Tom Cruise, Philip Seymour Hoffman, and Melinda Dillon.

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Magnolia may be Anderson's most sprawling, complex work, which also makes it disjointed and messy at times. Even Anderson himself later admitted the film was too long, though no one can deny that it's the product of a master filmmaker pushing himself to his limits.

5 Punch-Drunk Love

Adam Sandler and Emily Watson kissing in a doorway in Hawaii in Punch-Drunk Love

After Magnolia, it's easy to see why Paul Thomas Anderson decided to go for a more simplistic route with Punch-Drunk Love. The film features Adam Sandler in one of his best roles as a neurotic bathroom appliance salesman who falls for a woman played by Emily Watson. This film is a perfect example of the surrealness and absurdity that Anderson embodies so well in both his writing and directing.

In true Anderson fashion, Punch-Drunk Love can't just be a typical, heartwarming rom-com. As the film progresses, Anderson really dials up the intensity and the awkwardness that comes when a character as physically violent as Sandler's Barry Egan is forced to open up to a woman as determined as Watson's Lena Leonard. This may be the part of the film that loses some viewers, but they'll be guaranteed entertainment in the process.

4 There Will Be Blood

Daniel Day-Lewis kneeling at church in There Will Be Blood

In this epic starring Daniel Day-Lewis as a ruthless oil tycoon, Anderson proved that his expertise wasn't just in LA-based romantic crime movies. Here, Anderson coaxes possibly one of Day-Lewis's best performances of his career, all the while portraying a gritty picture of early 20th-century capitalism. And, yes, there is in fact blood.

Critics were quick to call it great when it was released in 2007, though others held their reservations when comparing it to other films released that year, like No Country for Old Men. For those who want to know why Paul Thomas Anderson is considered a brilliant director, this would be the movie to show them.

3 Licorice Pizza

Alana Haim and Cooper Hoffman running alongside each other in Licorice Pizza

His most recent flick, Licorice Pizza is Anderson's most personal film to date. It stars Cooper Hoffman (son of the late Philip Seymour Hoffman) and Alana Haim (one of three sisters in the rock group HAIM) as unlikely friends who question their attraction to each other, all against the backdrop of Los Angeles during the 1970's oil embargo. The movie is dominated by its two leads, though it also boasts a strong supporting cast with Bradley Cooper, Benny Safdie, and Sean Penn.

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Licorice Pizza is easily Anderson's loosest and lightest film, focusing more on the breeziness of innocent young love than on crime, drugs, and pornography. Thus, it's fairly easy to poke holes in. But what makes Licorice Pizza such a fun movie is in how effortlessly fun it is to watch these characters hang out, no matter how mundane it is.

2 The Master

Philip Seymour Hoffman and Amy Adams with the rest of the Dodd family in The Master

This was Paul Thomas Anderson's last film with Philip Seymour Hoffman before the latter's untimely passing in 2014. That being said, Hoffman is not wasted for a second of this film. He delivers one of the greatest performances of the 21st century as an L. Ron Hubbard-esque religious figure, who befriends Joaquin Phoenix's struggling World War II veteran.

It's easy to see why Anderson considers The Master his favorite film he's ever directed. Its greatness all comes down to the equal parts charm and powerhouse delivered by the three leads: Hoffman, Phoenix, and Amy Adams, who also gives an amazing performance that rivals her two co-stars. The movie is intense, disturbing, yet all the while engaging and immersive. Simply put, it's the best Paul Thomas Anderson can seem to do on a screen.

1 Boogie Nights

Marh Wahlberg, Burt Reynolds, Philip Seymour Hoffman, John C. Reilly, Julianne Moore, and Nicole Ari Parker posing for a photo together in Boogie Night

So, if The Master is the best Anderson can do, how does his iconic 1998 film Boogie Nights top it? When watching Boogie Nights, it feels like watching something unique and exciting. Anderson really establishes himself as something brand new in the film industry with this tragic parable of the pornography industry in the late 1970's and early 80's.

Mark Wahlberg stars as a young man who is roped into adult films by a suave director (played by Burt Reynolds). The film features an ensemble cast of characters who are all, one way or another, cursed by their involvement in this shadowy industry. Plus, it features another outstanding and wildly entertaining performance by Philip Seymour Hoffman. Any way you look at it, no film better encompasses what makes Anderson a unique and fascinating director like this iconic masterpiece.

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