One Battle After Another is gathering huge amounts of traction in the run-up to its release later this month, with the strong critical response suggesting that it may be on its way to the 2026 Oscars ceremony. This would be nothing new for auteur filmmaker Paul Thomas Anderson, who’s been nominated at the Academy Awards a total of eleven times.

However, despite this huge recognition by the Academy throughout his career, Anderson has somehow never won an Oscar. Even projects like There Will Be Blood and Magnolia, which are considered by many to be among the best movies ever made, lost the award to films that may not have aged quite as well. Many of them especially deserved to win in certain categories.

While I’m still hopeful that One Battle After Another‘s strong reviews will be enough to push PTA to his first Oscars victory, the filmmaker’s track record suggests otherwise. Thankfully, this creates a very compelling “overdue” narrative for Anderson, which could lead the Academy to vote in his favor to make up for their past mistakes.

Boogie Nights: Best Original Screenplay

While some directors spend their entire careers trying to get recognized at the Oscars, Anderson managed it with just his second feature. After making a name for himself with 1996’s Hard Eight, Anderson came back with an even bolder, more ambitious project in Boogie Nights, and the Academy couldn’t resist it.

1997 was a particularly strong year for cinema, with movies like тιтanic and LA Confidential taking up some room in Best Picture, but Anderson’s original screenplay for Boogie Nights was still considered among the five best of the year. While Ben Affleck and Matt Damon ultimately won for Good Will Hunting, the nomination alone was huge for Anderson.

As much as I love Boogie Nights, it’s hard to disagree with the Academy’s decision that year. Good Will Hunting‘s screenplay is an incredibly layered, profound story that marked the beginning of two of Hollywood’s most prolific careers in Affleck and Damon. Plus, Anderson would write even better movies than Boogie Nights in the years to come.

Verdict: Good Will Hunting deserved to win.

Magnolia: Best Original Screenplay

Two years after Boogie Nights, Anderson found himself nominated in the exact same category for his critically acclaimed follow-up, Magnolia​​​​​. The film is a true ensemble piece, following a group of eccentric characters whose lives intersect in powerful and unexpected ways. It remains one of Anderson’s most proficient screenplays, but it faced tough compeтιтion.

Magnolia went up against films such as American Beauty, The Sixth Sense, and Being John Malkovich at the Academy Awards — all of which had received immense critical acclaim upon their release. American Beauty would also go on to win Best Picture, so its victory in Best Original Screenplay wasn’t that surprising.

However, I’m confident that this is one of the several times Anderson truly deserved to win. Magnolia is arguably his most technical screenplay; the way he balances all of these characters and subplots is nothing short of masterful, and the film has certainly aged much better than American Beauty. Magnolia‘s ending may be divisive, but it’s a perfect display of Anderson’s screenwriting mastery.

Verdict: Magnolia deserved to win.

There Will Be Blood: Best Picture, Best Director, and Best Adapted Screenplay

After taking an eight-year break from the Oscars (Punch-Drunk Love didn’t receive a single nomination), Anderson came back stronger than ever with There Will Be Blood. The film received a total of eight nominations and even took home two awards: Best Actor for Daniel Day-Lewis and Best Cinematography for Robert Elswit.

But unfortunately, Anderson himself wasn’t victorious in any of his categories; in fact, he lost them all to the same film. No Country for Old Men took home Best Picture, Best Director, and Best Adapted Screenplay, leaving Anderson empty-handed for the third time.

Unfortunately, I have to admit that the Oscars sweep for No Country for Old Men was deserved. The film remains the Coen brothers’ best movie to date, and a complete technical masterclass. It was a commendable winner, even if it meant that Anderson had to be shut out once again.

That being said, it would have been nice to see the glory shared between PTA and the Coens rather than a complete sweep in one direction. There Will Be Blood would have been a worthy winner for Best Adapted Screenplay, as Anderson’s writing is what really stands out about this modern masterpiece.

Verdict: No Country For Old Men deserved to win Best Picture and Best Director. There Will Be Blood should have won Best Adapted Screenplay.

Inherent Vice: Best Adapted Screenplay

After failing to receive any recognition for The Master in 2013 (beyond three acting nominations), Anderson finally returned to the Oscars in 2015 with Inherent Vice. The film received two nominations in total: Best Adapted Screenplay and Best Costume Design. This was Anderson’s fourth time receiving a screenplay nomination — and his fourth time losing.

Inherent Vice faced tough compeтιтion that year, going up against Jason Hall’s American Sniper and Anthony McCarten’s The Theory of Everything​​​​​​. The award ultimately went to Graham Moore for The Imitation Game, which had collected a total of eight nominations across the ceremony.

While I stand by the fact that Anderson would have been a more deserving winner than Moore, the real masterpiece within the category was Damien Chazelle’s Whiplash. PTA’s overdue narrative was already beginning to form, but it’s impossible to bet against this standout debut screenplay, with its razor-sharp dialogue and fierce storytelling depth.

Verdict: Whiplash deserved to win, but Inherent Vice would have been a better winner than The Imitation Game.

Phantom Thread: Best Picture, Best Director

Thankfully, since Inherent Vice, the Oscars have learned never to overlook PTA again. For his next feature, the director received his second-ever Best Picture and Best Director nominations, with the film also collecting nominations for Best Actor, Best Original Score, and more. But still, Anderson didn’t win anything.

Admittedly, 2018 had a very impressive Best Picture lineup. With films like Lady Bird, Dunkirk, and Call Me by Your Name all competing for the top spot, it was never going to be easy for Anderson to finally break through. And yet, Phantom Thread would have been a more than deserving Best Picture winner.

Phantom Thread feels like such a powerful departure for Anderson, drifting away from the chaotic storytelling of his youth and towards a more profound, spiritual narrative that I would consider his most refined work to date. It’s certainly hard to compete with technical masterworks like Dunkirk and The Shape of Water, but I believe this is a much more important film.

Verdict: Phantom Thread deserved to win Best Picture and Best Director.

Licorice Pizza: Best Picture, Best Director, Best Original Screenplay

Anderson’s most recent film, Licorice Pizza, is perhaps the director’s most unfortunate performance at the Oscars to date. The film opened to rave reviews from critics, immediately cementing itself as a Best Picture contender and seemingly breaking PTA’s ongoing Oscars curse — until even more great films came along to steal its thunder.

This was a remarkably strong year at the Oscars, and one with even more brilliant films in compeтιтion than usual. In the Best Picture category alone, Licorice Pizza was facing hugely acclaimed films like Dune, Drive My Car, and The Power of the Dog. In any other year, Licorice Pizza could have easily carried PTA to his first win, but luck wasn’t in his favor.

Interestingly, my feelings towards which movie should have won these awards are different for each category. For Best Picture, I’m drawn to the visual and technical mastery of Jane Campion’s The Power of the Dog, which was a clear frontrunner for a long time. For Best Director, however, it’s hard to argue against the dazzling visual creativity of Steven Spielberg’s West Side Story.

If there’s one category where PTA could have finally been awarded his overdue Academy Award that year, it’s Best Original Screenplay. The filmmaker has more nominations in screenplay categories than any other, and Licorice Pizza really thrives in its lighthearted, naturalistic writing and lovable characters.

Verdict: The Power of the Dog deserved to win Best Picture, West Side Story deserved to win Best Director, and Licorice Pizza deserved to win Best Original Screenplay.