Counting down Brad Pitt’s 20 best performances

To mark the Oscar-winning star's 60th birthday, we're taking a closer look at the finest roles from Brad Pitt's expansive career

Film Features Brad Pitt
Counting down Brad Pitt’s 20 best performances
A River Runs Through It (screenshot), Fight Club (20th Century Fox), The Curious Case Of Benjamin Button (Paramount Pictures) Graphic: The A.V. Club

The remarkable thing about Brad Pitt, who turns 60 on December 18, isn’t the 85 and counting IMDb acting credits under his belt, although that’s a pretty impressive number. Rather, it’s that Pitt remains the kind of A-list actor who’s continually searching for new ways to ply his craft and deliver fresh performances for audiences.

From intense dramas to breezy comedies to heist thrillers, Pitt brings his unparalleled charisma and classic movie star looks to an impressive array of projects. And as this list of his 20 best roles indicates, the guy’s pretty much never given a dull performance. In fact, The A.V. Club team had a tough time deciding which of his beloved and iconic characters couldn’t make the cut. Here, then, to mark the iconic star’s milestone birthday, is our look at Pitt’s best work.

previous arrow20. True Romance (1993) next arrow
True Romance (1993) Official Trailer # 1 - Christian Slater HD

In a movie dominated by outstanding and unforgettable supporting roles (almost cameos, really) few have endured like Brad Pitt’s Floyd, the slacker stoner roommate to Michael Rapaport’s Dick Ritchie, . The role in and of itself is hilarious: Floyd is the type of guy everyone knows, and not in a good way. But there’s a lovability that comes with the know-it-all grungy stoner who does nothing but wander about and lay in a haze of weed smoke, and Pitt turns this role into a special one. When the film premiered in 1993, Pitt was dipping his toes into odder roles to prove he was more than just a sex symbol (after Johnny Suede and Kalifornia and before Seven and 12 Monkeys). While the decidedly dressed-down role allowed Pitt some forever quotable lines and props, the killer line delivery comes when Floyd, tiring of a smug gangster’s (James Gandolfini) line of questioning, sneaks in the line, “condescend me, man, I’ll fucking kill ya.” It’s just a great, teeny role from one of the best character actors ever. [Don Lewis]

134 Comments

  • breadnmaters-av says:

    I’m not a Pitt fan – not even close but I liked Fight Club and Meet Joe Black. There are a dozen other of his movies that I would like to enjoy but – I hate to write this – the guy talks like he has a dick in his mouth. And not in the “plummy” way that some British toffs speak.

    • dudull-av says:

      Things that bother me is why there’s no sexual allegation on Brad Pitt. Is he actually a gentleman or women think he’s very attractive that any claims will not blow up like what happened to less attractive actor?

      • nilus-av says:

        Plenty of very attractive men have been #MeToo’d so if Pitt was a real asshole, it would have come out.

      • nogelego-av says:

        Maybe it’s for the same reason his best and most memorable roles are ones where his romantic co-stars are men (George Clooney, Leonardo DiCaprio) rather than women? I mean, the guy made TWO movies where he was pretending to be in a heterosexual marriage – once to win World War II and the other where he played a guy hiding a big secret from his wife (Mr. and Mrs. Smith) – who also had a secret from him. How big of a neon sign do you need?

      • theotherglorbgorb-av says:

        Sorry, that bothers you? Sheesh.

      • recognitions-av says:

        Well there was that whole thing about him maybe beating Angelina and his kids and how his kids don’t want anything to do with him now

        • CashmereRebel-av says:

          Allegedly. And it was between him and the oldest son. And it was on a private plane, so Angelina “may have” leaked it to the press herself in order gain an advantage in any future custody battles. I don’t have a dog in this race, but the courts, and CPS investigation, both ruled in his favour. 

      • earlydiscloser-av says:

        Consider this: perhaps he has never sexually assaulted anyone. Also: that is an odd thing to be bothered by.

      • peon21-av says:

        There are numerous shitty-father allegations coming out of the Pitt/Jolie divorce, but they’re of the non-sexual variety.

  • bustertaco-av says:

    How did Snatch not make the list? It’s a pretty unique role in a movie that’s better than at least half the movies on this list. And it’s definitely memorable.

    • mysteriousracerx-av says:

      Yeah, that seems like a pretty obvious omission, and a super fun role, and like you, I’d probably put that in the top 10 somewhere.I read about people (esp. US audiences) complaining that they had a hard time with accents in other Ritchie films, and then he brings in Brad Pitt for Snatch, hahaha, but still gives him nearly incomprehensible dialog 😀

      • nilus-av says:

        I think Ritchie did in on purpose as a giant F-You.  “So you can’t understand our heavy accents?  Okay I am gonna hire an American and have an accent so intense, unique and hard to understand that other characters in the movie can’t understand him”

        • mysteriousracerx-av says:

          Oh yeah, that was in the article I read, I did a pretty shitty job of relaying the whole idea behind the Pitt casting/dialog, and that I was referencing an article about it, duh, hahaha … I blame it on just getting back from a trip … and the booze.

      • coatituesday-av says:

        gives him nearly incomprehensible dialog
        And, oddly, authentic dialog. (Seriously, an Irish friend of mine used to encounter tinkers all the time and SHE said Pitt’s accent was perfect.)And yeah, why the hell wasn’t Snatch on here?

      • rauth1334-av says:

        lol us audiences. bullshit. 

    • drkschtz-av says:

      Snatch is a classic

    • bcfred2-av says:

      Beats the ever-loving shit out of Legends of the Fall, which is the movie where he came perilously close to disappearing up his own ass by Acting. So. Hard. The Mickey supercuts on YouTube are fucking priceless, and I can’t imagine too many other actors being able to pull off that ridiculous accent, flash that much charisma and have the physicality to believably play a pikey bare-knuckles boxing champion.Either he has enough self-awareness or someone got through to him that he needed to be more than a pretty boy (though Floyd appeared in the middle of his early run). Clooney as well. Hey Brad, you’re a talented actor and the best-looking leading man in Hollywood. Choose your roles with confidence (and he has, ever since). After this he had Seven, 12 Monkeys, Sleepers (unfairly forgotten), Devil’s Own (fairly forgotten), and then after Seven Years in Tibet and Meet Joe Black went on a run of almost entirely offbeat or goofball roles.

    • crews200-av says:

      Definitely better than Ad Astra. How can a movie with literal moon pirates be so damn boring?

      • frankwalkerbarr-av says:

        I liked the moon camouflage uniforms. Which they wore under their spacesuits. So, I guess they could hide if they were suitless on the moon’s surface?

      • maulkeating-av says:

        Is that what that fucking thing was about? There were moon pirates? Literally had no idea.

    • rauth1334-av says:

      I came here to see that on the list (no the slide show i know ways)PLUS he takes his shirt off. I mean cmon!!

    • tobydrake-av says:

      D’ya like dags?

    • typingbob-av says:

      Because Pitt was in REAL Tarantino films?

    • fistfullofbees-av says:

      The best thing about Snatch: when you went to a bar and found a Snatch fan, and, drunk, started speaking in Pikey to each other, yet still understood everything you were saying to each other!
      Met one or two of my best friends that way!

  • kirivinokurjr-av says:

    I’d put Moneyball at the top, both for the movie being so incredibly rewatchable and for Pitt’s lovely work.

    • elvis316-av says:

      I penalize it for making Pitt Billy Beane when Art Howe got C. Philip Hoffman? If Snatch is not on this list, it is incomplete.  And it is a slide show so I cannot participate. 

    • bcfred2-av says:

      It runs pretty consistently on basic cable. Just caught it again on Sunday afternoon. He’s perfect in the role, still cocky (as pro athletes tend to be) but with just enough real world beaten into him.Moneyball and Social Network are exhibits A and B of movies about subjects that should be boring as all fuck but are instead compelling entertainment. I think it’s because neither takes a moment to slow down too much and let you remember it’s a movie about assembling a baseball roster or building a social media company.

    • captain-splendid-av says:

      I like Moneyball, but no way is it better than Jesse James.

    • Rev2-av says:

      I never finished the movie. Felt like it was made by a machine. Sapped all of the humanity out of the story.

  • noyousetyourusername-av says:

    The lack of Snatch and True Romance is a horrific crime

    • zirconblue-av says:

      True Romance is on the list (#20).

    • bcfred2-av says:

      TR’s the very first slide, but agree fully on Snatch. Alongside Burn After Reading and maybe Thelma & Louise, probably his most fun role.

      • nilus-av says:

        Burn After Reading is a movie ahead of its time. When it came out, thinking the government could be that incompetent and that a conspiracy could be run by that many buffoons’ seemed out of this world.  Then 2016 happened and we kinda learned that its not

        • bcfred2-av says:

          I don’t know, I know some people who worked in DC for a long time and success there seems to be mostly about blame-shifting, attaching yourself to the right people/candidates, and tenure. There are rarely metrics for tracking success or failure, and to the extent there are people aren’t rewarded or penalized for it. I know this sounds like the corporate world as well, but at some point people there do get fired for incompetence.

          • fever-dog-av says:

            “There are rarely metrics for tracking success or failure”Almost to my 20. I hear DOD does it well but not so much other agencies. There are performance measurements but they’re easily gamed. In reality, “hallway rep” is how it’s decided and the “Type As” tend to win out. Many of those are all hat no cattle or abusive towards subordinates while making their bosses look good. Some are fine.

          • bcfred2-av says:

            I’m not necessarily talking about the military/law enforcement/intelligence side of government, which in fairness is more relevant to a discussion about BAR. Although you’d think whoever orchestrated the Afghanistan withdrawal last year would have been sacked. I was thinking more about all the grand proclamations that are made whenever some expensive new program is introduced, then never spoken of again except in generalities.

        • CashmereRebel-av says:

          Frances McDormand’s reaction to Clooney’s invention is one of the funniest things I’ve ever seen. I have no idea why it isn’t an oft-used gif. 

    • noyousetyourusername-av says:

      Honestly I hate the slideshows so much that I just shot it through it as quickly as possible, my bad.

  • magpie187-av says:

    Cutting Class should have made it in. It’s a lot of fun & his performance makes the movie. 

  • maulkeating-av says:

    How much glue does Spanfeller make you sniff before you put these things together?

  • hootiehoo2-av says:

    Glad 12 Monkeys was ahead of Fight club, I love Fight Club but 12 Monkeys was fucking great.And as others have said, how the fuck is Snatch not on this list. Snatch is probably his movie that I’ve rewatched the most. 

    • nilus-av says:

      I am gonna rewatch it tonight.  

    • rogue-like-av says:

      I honestly never realized how many films Pitt has been in, let alone how many he’s in that are in semi-constant rotation for me. Between Se7en, 12 Monkeys, ARRTI, Fight Club, and any random Ocean’s films, I probably watch one film with Pitt in it a month. Slide shows are still the worst. 

  • redwolfmo-av says:

    I LOVED Ad Astra and would kill for a directors cut removing the voice over narration just to see how it goes

    • noisetanknick-av says:

      I liked Bad Dad Space Dad in spite of itself and would definitely be interested in seeing how it plays without the heavy-handed narration cropping up repeatedly to break the trance.

    • coatituesday-av says:

      I liked Ad Astra so much… the narration part I kinda forgave because… I don’t know, they pad movies with that because they think we’re all too dim to figure out an even slightly complicated plot or setting. Eventually, like 20 years from now, we’ll get a narration-free dvd set, like with Blade Runner.

    • andysynn-av says:

      It really is a fantastic film – I remember the early reviews for it were all clearly a case of “let’s copy each other so we can say there’s a critical consensus” but after watching it it was very clear that, in their rush to agree with each other and pat themselves on the back, most of them had missed the point entirely.This is why you shouldn’t copy someone else’s homework, kids.

  • aap666-av says:

    Im a Pitt and QT fan and I hate OUATIH

  • soosheeroll-av says:

    Maybe I’m weird, but I loved Mr. and Mrs. Smith. I thought it was really fun and had decent action. 

    • seinnhai-av says:

      Nope, not weird.  It was fun.  However it was in that “Pitt being Pitt” era along with all the Ocean’s movies.  Not high on the acting chops list.

    • ReasonablySober-av says:

      It’s my favorite example of Fun Pitt. I will 100% stop and watch whenever it’s on cable.

  • klyph14-av says:

    Meet Joe Black was unfairly maligned at the time of its release, but is now widely admired.

    I have never heard of this “Meet Joe Black is actually good” redemption tour.  I feel like this is borderline astroturfing.

    • nilus-av says:

      Benjamin Button as well was not well loved by audiences and its still not good

    • benjamin6gates-av says:

      That unfortunate Rastafarian accent in meet how black tho. Not good. #NeverForget

    • ReasonablySober-av says:

      Even as someone who loved Meet Joe Black back when it came out, I’m extremely confused at it getting praise as an underrated classic.

    • electricsheep198-av says:

      I hadn’t either but I’m here for it. I’ve always loved that movie and I thought I was the only one.I’m still not sure I’m not the only one. lol

    • pinkkittie27-av says:

      I don’t know how this could be considered good acting when literally it’s like Elf but a total bummer — child-like grown man shows up in Serious Business and Family situations and does awkward shit, acting really confused and amazed all the time.This movie never ceases to irritate the ever-loving shit out of me if I see a clip.Peanut butter good. Gorgeous, nice woman doctor easy to love. Admirable man is admirable but pretty oblivious to the women around him. Derp. Derp. Derp.

  • azubc-av says:

    Not surprised Seven Years in Tibet didn’t make the cut; however, I do have a soft spot for the film and it’s quite loyal to the source material (H. Harrer’s book), and Pitt plays Harrer quite well (he was a bit of an arrogant asshole in real life).

  • pmdmke-av says:

    1. The Counselor2. Killing Them Softly3. The Assassination of Jesse James by the Coward Robert FordEverything else

  • erakfishfishfish-av says:

    I am not a fan of Benjamin Button by any measure. It was basically David Fincher’s take on Forrest Gump: a big swing that fouled back into the broadcasters’ booth.

  • TeoFabulous-av says:

    Not a single mention of Pitt as Metro Man in Megamind??

    • nilus-av says:

      I know its a hot take but I think Megamind is the one of the better Dreamworks Animation movies. Its kind of funny, I like a lot of their least successful films because they get to stand alone. The successful ones get turned into franchises and just ran straight into the ground. I will gladly watch Megamind, Turbo or Peabody and Sherman again before I turn on any of the Shrek or Madagascar movies

      • TeoFabulous-av says:

        Megamind is one of my favorite animated movies. Somehow, it just hit the sweet spot for me. Kung Fu Panda (the original, not the sequels) was also a great Dreamworks animated movie. How those movies came out of the Shrek assembly line with any soul is beyond me, but I’m glad they exist.

    • seinnhai-av says:

      You’re gonna complain about that and not about his role as Vanisher in Deadpool 2?  You have no shame, do you?

  • cura-te-ipsum-av says:

    I’m pretty sure Fight Club’s actually one of Edward Norton’s best roles.

  • tigernightmare-av says:

    I haven’t seen Moneyballs or Hollywood, but 12 Monkeys is my favorite performance of his, as well as Bruce Willis’, who played James Cole with such a vulnerable innocence.I did not like 12 Years A Slave, a movie that makes the viewer think, “Oh, maybe this white guy will save him,” at least three times. The best, most apt description I ever heard for it is, “Passion of the Christ with a happy ending.”

    • frankwalkerbarr-av says:

      You do know 12 Years a Slave was a true story based on the memoirs of Solomon Northup, right? It wasn’t a made up story like the Bible.

      • tigernightmare-av says:

        It was still a terrible movie. Solomon himself had no agency. He was at the whims of multiple helpful white friends and completely dependent on them for his freedom. Even if that really happened, it doesn’t give the screen version of him any depth.The film gave me narrative blue balls. Like South Park said, you can’t just torture a guy for two hours. You can tell a true story without making it so shallow. I was left wondering more about the people who had been carrying out these abductions and if they were ever brought to justice. And life after being a slave is part of the story, too.It’s also not a faithful adaptation, nor is it historically accurate, as this film/book comparison from CliffsNotes shows:For example, the slave trader Goodin is
        eliminated from the story, along with Northup’s experience in his
        possession. The slaves Arthur and Clemens Ray are combined into one
        character, with the latter being rescued in New Orleans instead of the
        former. Northup’s time with William Ford is abridged, while the role of
        John M. Tibeats is inflated for the screen—the role is combined with
        other minor characters and played more as a crazy man than the bitter,
        angry man of Northup’s narrative. Only one of Tibeats’ murder attempts
        is shown, though it is embellished for dramatic effect. Both Platt’s
        harrowing nighttime escape in the swamp and his time at Peter Tanner’s
        plantation are eliminated completely, and some of Tanner’s role is added
        to Epps instead.The movie lays the blame for Northup’s sale to
        Epps directly on William Ford, when in fact it was Tibeats who sold
        “Platt” to the notorious “n***** breaker.” Even worse, the film suggests
        that after Tibeats’ murder attempt, Northup told the righteous Ford
        about his status as a free man and begged Ford to help him. According to
        the movie, those pleas fell on William Ford’s deaf ears. The facts,
        however, are much different.Like Northup’s real-life experience, the bulk of the film version of 12 Years a Slave
        is seen on Epps’ plantation. Here, the film concerns itself chiefly
        with the sorrows of Patsey and, in that regard, stays fairly true to the
        memoir. However, that means the film downplays or eliminates events in
        Northup’s personal story and generally ignores other significant events
        that happened to slaves Abram, Wiley, and others. Also, Northup/Platt’s
        eight-year role as the slave-whipping driver on Epps’ farm is completely
        omitted, except for the one brutal whipping of Patsey. Henry B.
        Northup—the man who actually rescued Solomon from slavery—is not
        included in the film. The entire trial and acquittal of James H. Burch
        is also omitted, reduced to a text-only postscript as a prelude to the
        final credits.

  • seven-deuce-av says:

    I submit that The Curious Case of Benjamin Button is fucking terrible. Would have made a fun episode of The Twilight Zone, but at 166 mins it’s an egregiously long stretch on the short story it’s loosely based on.

  • zwing-av says:

    Kalifornia isn’t a great movie but it’s one of his best performances. I think at least that deserves a mention over Benjamin Button or Legends of the Fall. 

    • Gorodisch-av says:

      I strangely agree with you about Kalifornia and I haven’t seen it in a long time. It jumped into my mind for a top 20. Does it hold up? I’ll track it down again.

      • zwing-av says:

        Watched it a few years ago – I’d say it’s very dated but enough of it holds up that it’s worth watching.

    • dummytextdummytext-av says:

      I really like Kalifornia, personally. Underrated. 

  • iwontlosethisone-av says:
    • seinnhai-av says:

      If I had a dollar for every time I’ve said this line, I’d have enough money to buy Paltrow’s head in a box.

      • maulkeating-av says:

        Man, Goop sells some weird, pricey shit.

      • fever-dog-av says:

        I say it in front of my kids every time we get Amazon.  They’re getting into their late teens now so I’m so close to them watching the movie and, I dunno, maybe laughing out loud at the scene?

        • seinnhai-av says:

          I’m sure they’ll be fine, unless of course you’re holding a gun on them when you ask. Unless you’re in Idaho or Montana, in which they’ll be “fine” by local standards.

        • mysteriousracerx-av says:

          Hahaha, holy shit, a kindred spirit! I do this too, and really lean into it, “What’s in the box? WHAAAAATS IIIIINNNN THE BOOOOOOX???”My daughter mostly just stares at me, slightly confused. 😀

          • fever-dog-av says:

            Now my kids say it without even knowing the origin. I also used to say things like “it puts the dishes into the dishwasher” or “it turns the light off after it leaves a room” but that Silence of the Lambs South Park episode spoiled that one.

      • pearlnyx-av says:

        You’ll have to settle for her pussy candles.

    • hendenburg3-av says:

      Possible Hot Take, but what got me about that line was just… how WHINY Pitt sounded. Granted this could be because I only saw Seven a few years ago and so I had been hearing references to that line long before I saw the actual movie 

    • svendalyn-av says:

      I love this scene just for the William Shatner parody.

  • jackstark211-av says:

    What about Kalifornia?

  • scobro828-av says:

    I think his work in Deadpool 2 at least deserved a nod of recognition. 

  • gallagwar1215-av says:

    It’s almost like you watched the first 5 films on the list and then just went through his IMDB and filled out the other 15 at random.1. Once Upon a Time
    2. Moneyball
    3. Fight Club
    4. Se7en
    5. 12 Monkeys
    6. Inglorious Basterds
    7. Snatch
    8. Benjamin Button
    9. Ocean’s Eleven
    10. The Assassination of Jesse James
    11. The Big Short
    12. Ad Astra
    13. True Romance
    14. 12 Years a Slave
    15. Burn After Reading
    16. Thelma & Louise
    17. A River Runs Through It
    18. World War Z
    19. Kalifornia
    20. Fury

  • electricsheep198-av says:

    I’m glad to see Meet Joe Black so highly listed.  I love that damn movie.  Brad Pitt is so great.  

  • rigbyriordan-av says:

    You did NOT seriously put Meet Joe Black 2 fucking spaces ahead of Inglorious Basterds. … You absolutely DID NOT DO THIS. 

  • tkincher-av says:

    I agree that Snatch is a glaring omission. And while I know it’s not greatly popular, I really liked The Counselor— and I’d certainly take it over Benji Buttons, Legends of the Fall, or Meet Joe Black.

  • bikebrh-av says:

    I’ve seen most of these movies, but I won’t watch that Jesse James movie because fuck that racist cousin-fucking(look it up) confederate terrorist piece of shit. Anybody who put a bullet in him was a hero. I see enough crap lionizing him here in Missouri, I don’t need to watch a movie about that piece of shit.

    • fever-dog-av says:

      Are you saying he didn’t steal from the rich and give to the poor?  

      • bikebrh-av says:

        There is certainly no evidence of that. He was mostly just a lifelong domestic terrorist and criminal. I’m sure the MAGA’s love him.

        • fever-dog-av says:

          Yeah I was referring to the song which, if you aren’t familiar with it, will make your head explode.  Even as a teen knowing next to nothing about James it seemed stupid the first time I heard it.  

          • bikebrh-av says:

            I may have heard it decades ago, before I learned what a shitbird he was….Coming back from looking it up. I probably heard either the Kingston Trio version, or the Pete Seeger version(wouldn’t be the first time that Pete didn’t do his research, as much as I did like him). There were albums by both in the house when I grew up in the 1970’s.

    • oldaswater-av says:

      Apparently he only killed the unarmed and helpless. 

  • jpfilmmaker-av says:

    Can we talk about not doing these things as fucking slideshows?

  • szpowell-av says:

    Fury seems to be forgotten now, but I just watched it. It was DAMN good, including Pitt’s role.

  • amoralpanic-av says:

    one can debate whether or not the use of the 2008 presidential election to bookend the film worksIt absolutely works. Now fucking pay me.

  • earlydiscloser-av says:

    Sure but… as if Brad Pitt (or someone called ‘Cliff’) could lay a finger on Bruce Lee. 

  • rottencore-av says:

    god i love killing them softly.

  • volunteerproofreader-av says:

    This … is not how ellipses work

  • theghostofoldtowngail-av says:

    Get rid of Legends of the Fall, Meet Joe Black, and Benjamin Button.I’d put Snatch, Kalifornia, and The Mexican (a movie I unironically enjoy far more than I probably should) on the list instead. The other two have more to do with my own personal likes than objective quality, but I cannot believe Snatch wasn’t included over some of the choices that made the list.

    • bcfred2-av says:

      Responding to this more than a year later since they just reposted the list for Pitt’s 60th birthday, but…Yeah The Mexican is fun in the same way a lot of sort of caper-y movies were at that time. Reminds me a bit of Get Shorty, just colorful characters everywhere with a likeable protagonist at the center.

    • dummytextdummytext-av says:

      Kalifornia is comically underrated

  • devinoch-av says:

    Why the hell is Spy Game not on this list?

  • electricsheep198-av says:

    I’m glad to see Meet Joe Black ranked so highly. I’ve always loved that movie. Is it a bit of a slog? It kind of is, especially because I don’t think we were or are used to movies that really take their time like that. But the story is engaging and affecting, and Pitt’s Joe is impossible to look away from. That one always brings tears.

  • svendalyn-av says:

    Needs more Johnny Suede…

  • morcheeba616-av says:

    OUATIH is so overrated

  • retroxcellence671-av says:

    I can’t stand watching or hearing people eat. I could barely make it through Oceans 11 because of Rusty

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