Few actors have been in as many classic movies as Jack Nicholson, whose humble beginnings in the 1960s (mostly supporting roles in B-movies) gradually raised his profile, with an Oscar nomination by that decade’s end. During the 1970s, he reached a level of stardom that made him one of the most celebrated actors of his generation, and his reputation is still strong to this date, even with the actor retiring in 2010.

He's one of the most-nominated actors in Oscar history, and with three wins to his name, he joins a prestigious club of actors with only six members (while only one person, Katherine Hepburn, has won four Oscars for acting). Those 12 movies that earned Jack Nicholson an Oscar nomination for action are ranked below, not necessarily by how good Nicholson is in them (though that plays a role), but by how good they are as movies overall, starting with the decent and ending with the great.

12 'Ironweed' (1983)

Director: Héctor Babenco

Ironweed is probably the most obscure movie for which Jack Nicholson received an acting nomination at the Oscars, and there’s an argument to be made it’s also the worst film in this category. It sounds like it could be something on paper, especially because Nicholson stars alongside fellow three-time Oscar winner Meryl Streep, and indeed, both were nominated for the performances they gave.

But the film itself is a little boring, sadly, revolving around two people having a tumultuous relationship following the Great Depression; Nicholson’s character being defined by his alcoholism, and Streep’s being terminally ill. Given the story and when the movie’s set, Ironweed isn’t supposed to be a fun time, but it would’ve been nice if the drama had just been more compelling. The two leads do their best with what they’re given, but it’s probably only worth seeking out for the most dedicated fans of either.

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11 'As Good as It Gets' (1997)

Director: James L. Brooks

Proving successful critically, commercially, and awards-wise upon release, As Good as It Gets not only got Jack Nicholson his penultimate Oscar nomination, but also his third and final win. In the film, he plays an intensely unlikable individual who strikes up a relationship with a younger woman and slowly – very slowly, considering the nearly 2.5-hour runtime – learns to be a bit less of a jerk to those around him.

Just like how the depression of Ironweed was intentional, the meanness of As Good as It Gets is a part of the film, but nowadays, it feels like it pushes things a little too far while also giving the main character too simple and unearned a redemption arc. It might’ve worked for the 1990s, and people clearly liked Nicholson’s performance and the film as a whole, but it’s aged kind of lousily, to be perfectly honest.

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10 'Prizzi's Honor' (1985)

Director: John Huston

Things start to turn around a little here, because even though Prizzi’s Honor isn’t amazing, it is surprisingly good, and it’s possible to even call it one of Jack Nicholson’s more underrated movies. He plays a hitman who works for a very wealthy crime family, though beyond being about crime, it’s also a romantic comedy, given much of it revolves around Nicholson’s character falling for a woman who’s also an assassin.

Beyond Nicholson, two other people got Oscar nominations for their roles in Prizzi’s Honor: William Hickey and Anjelica Huston, with the latter also winning. As far as darkly comedic crime movies from the 1980s go, it generally works fairly well. It can’t be called a criminally overlooked film, but it’s definitely a little overlooked, seeming to have an impact upon release (it got eight Oscar nominations) without necessarily being remembered as a classic. It's not, but it's also far from bad.

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9 'A Few Good Men' (1992)

Director: Rob Reiner

A highly-regarded courtroom drama, A Few Good Men stands out within the genre for not being about a typical criminal or civil case, but instead centering on military law. Namely, the case at the center of A Few Good Men involves a pair of U.S. marines being on trial for allegedly killing another, with the case unfolding certain complex secrets that some individuals would rather be kept suppressed.

Those well-versed with movies that are largely set in courtrooms might not find a ton here to be surprised by, even with the plot of the film involving a court-martial, but it’s still generally well-acted, presented, and written. Jack Nicholson has something of a villainous role here and makes the most of his somewhat infrequent screen time, succeeding – as he often does – at stealing the scenes he does show up in.

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8 'Reds' (1981)

Director: Warren Beatty

Reds is an absolutely huge movie with a remarkable cast, and stands as one of the longest-ever movies to get a Best Picture nomination at the Academy Awards. Directed by and starring Warren Beatty in what’s clearly a passion project, it tells a story based on true events about U.S. journalist John Reed being inspired by what he witnessed of the October Revolution in Russia during the 1910s, and set about trying to introduce socialist ideas in his home country.

It spans many years, and on top of being a historical drama, also works in an element of romance, which involves Nicholson’s character, playwright Eugene O'Neill, being involved with activist Louise Bryant (Diane Keaton), whom Reed is also in love with. Reds bites off a good deal and manages to chew the majority of it, and it ended up being nominated for a staggering 12 Oscars (ultimately winning three).

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7 'Terms of Endearment' (1983)

Director: James L. Brooks

Terms of Endearment isn’t the only Best Picture winner Jack Nicholson appeared in, given he also starred in the winner for 2006, the Martin Scorsese crime/thriller, The Departed. However, he wasn’t Oscar-nominated for his (very entertaining) performance there, so that’s the only time that movie will get mentioned here. Also, another notable omission: Nicholson wasn’t nominated for an Oscar for his role in The Shining, even though that’s typically regarded as one of his best films.

Anyway, back to Terms of Endearment. It was a well-awarded dramedy that mostly revolved around the relationship between a mother and her daughter, and the way their dynamic was further challenged by the latter getting diagnosed with cancer. Nicholson won an Oscar here, his second overall and his only one for a supporting performance, playing a retired astronaut/neighbor of the mother character, who was played by Shirley MacLaine (who also won an Oscar for her role). It’s a good movie. Not great, nor the best of the Best Picture winners, but it works well as a quintessential cinematic tearjerker.

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6 'Easy Rider' (1969)

Director: Dennis Hopper

While it’s certainly a product of its time, there is something inherently compelling about Easy Rider that endures some 50+ years later. And, at worst, most will be able to appreciate what it was for its time, and how radical it would’ve seemed at the time of its release: a moment in history that itself was – at least in hindsight – rather tumultuous and tied with a certain rebellious spirit.

That all might sound a little lofty and vague, but that’s because it’s hard to talk about Easy Rider in the traditional sense, given there’s little by way of narrative, by design. It’s a road trip sort of movie about two bikers going on a long – and potentially doomed – journey, with everything getting progressively darker and more psychedelic as it goes along. It’s a film that’s earned its reputation as a decade-defining cult classic, and is also a pivotal one within Jack Nicholson’s body of work, seeing as it earned him his very first Oscar nomination.

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5 'Five Easy Pieces' (1970)

Director: Bob Rafelson