Leonardo DiCaprio hasn't endured as a fixture of American pop culture isn't just because he's a great actor, which he is. It's also his willingness to play any part, regardless of how bad it might make him look. It just so happens that many of his most memorable roles are the ones where he comes off the absolute worst. Take his stock broker in The Wolf of Wall Street, for example, or the heinously racist plantation owner in Django Unchained. These performances tend to stick in my memory far more than most of the ones where Leo plays a person we're supposed to like.

Warning: The following contains spoilers for several of DiCaprio's older films, along with his latest, Killers of the Flower Moon.

Killers of the Flower Moon is another one of these films. Here, Leo plays Ernest Burkhart, a man who helps his uncle try to steal oil money from the Osage people by marrying into an Osage family and then assisting in murdering all of them. For those not familiar with the true story on which Martin Scorsese's film was based, you might get the impression from the ads that Ernest Burkhart could be a White Savior character--but it ain't true, I assure you.

But, of course, Ernest is just one of many Leonardo DiCaprio characters who could use a little bit of facial rearranging. His filmography, as mentioned, is pretty stocked with guys who, for one reason or another, would very likely benefit from some tough love. Not every role he's taken in his three-plus decades of his career has been one of these, but Leo's skill as an actor, his broad choice of roles, and his boyish good looks have combined to produce a number of character's we've had strong reactions to. Let's go through them, in order of release.

1. Romeo + Juliet

While the play is generally considered a very serious and dramatic tragedy, I've always been of the school that thinks of Romeo & Juliet as a dry, satirical comedy. Baz Luhrman's very entertaining hybrid adaptation, which keeps the old dialogue but tells the story in a present-day setting, is so self-serious about this case of puppy love that Romeo comes off as extra cringey.

2. Catch Me If You Can

Leo plays the teenaged check-forger Frank Abagnale in Steven Spielberg's delightful crime flick--he's a spoiled, out-of-control kid who lost it after his parents got divorced. Maybe he just needed a good slapping from Tom Hanks.

3. Revolutionary Road

Sam Mendes' interminable drama about marital and suburban ennui--it's basically American Beauty again but in the 1950s--is pretty mundane, and Leo's Frank Wheeler is just a crappy man and husband who doesn't have much of anything going on. The movie ends in tragedy because of that extreme nothingness that exists at the core of his being.

4. Inception

Leo's character, Cobb, is a master of dream heists who is constantly at risk of being trapped inside one of those dreams. He's got a spinning top that he uses to keep himself grounded. If the top spins forever, he's in a dream; if it eventually falls over, he's in the real world. At the end of the film, we see him spin the top, and the movie cuts to the credits before it stops. It's intended as an ambiguous ending, but it seems like Cobb might need to be slapped awake.

5. J Edgar

Clint Eastwood is pretty hit or miss as a filmmaker, and J Edgar is not one of the hits--this is a movie that will be remembered more for the subpar old-age makeup that Leo and Armie Hammer had to sport for the movie. Leo, as the titular founder of the FBI, does his typical good work, but we're talking about the real-life J Edgar Hoover here. This is a man who is most famous now not for originating the FBI, but for his copious abuses of power. That's a person who definitely deserved a good smack upside the head.

6. Django Unchained

There's not much that needs to be said about Calvin Candie, the plantation owner who likes to make his Black slaves fight each other, among many other cruelties, in Quentin Tarantino's revenge thriller. This is a character with no redeeming qualities--but he certainly got what was coming to him.

7. The Wolf of Wall Street

This Scorsese flick might be his most entertaining movie ever, and that's thanks in large part to DiCaprio hamming it all the way up as the titular wolf, Jordan Belfort. While Leo didn't win an Oscar for this one, he seemed to be having a pretty great time dialing it up to 11 as often as possible. The Belfort character is such a fun trainwreck.

8. Once Upon a Time in Hollywood

Rick Dalton is a washed-up Hollywood star who is struggling to deal with all the insecurities that come with that sort of life situation--but in contrast with Brad Pitt's stuntman Cliff Booth, Rick is handling this change in status poorly because he's obsessed with appearances and what people think of him. Leo is a perfect fit for the character, who we watch with pity for the most part.

9. Don't Look Up

Dr. Mindy starts out as hero, helping discover the comet that's about to slam into the Earth and destroy human civilization. But then he enjoys the trappings of fame a little bit too much and becomes a celebrity and a part of the Big Media establishment, undercutting his own attempts to sound the alarm after being seduced by a sexy news anchor played by Cate Blanchett.

10. Killers of the Flower Moon

Ernest Burkhart falls in love with and marries an Osage woman named Molly--but his marriage is really part of a plot by Ernest's uncle William to murder Osage folks and steal their oil money. Ernest is shown as both implicit in William's plan and reticent about it, but ultimately he never manages to make any of the right moral choices.