22. Roger Ferris, Body of Lies (2008)
What it’s about: CIA officer Roger Ferris (DiCaprio) attempts to catch a jihadist terrorist named Al-Saleem (Alon Abutbul).
Biggest asshole moves: Really, it’s just his crude, bro-y language. (See: “I need to take a shit, I need a shower and an internet connection”…and the above.)
Most redeeming moment: Everything Ferris does is for good reason. He gives himself up to Al-Saleem in an effort to save the woman he loves, which eventually leads to him being badly beaten and losing two fingers.
21. Jack Dawson, Titanic (1997)
What it’s about: A 17-year-old first-class passenger named Rose DeWitt Bukater (Kate Winslet) finds an unexpected companion in the penniless young artist Jack Dawson (DiCaprio) on the ill-fated Titanic in 1912.
Biggest asshole moves: He blatantly flirts with Rose in front of her douche of a fiancé, Cal Hockley (Billy Zane), and then draws her naked (aka like “one of [his] French girls”). Oh, and kisses her. And has steamy sex with her in a car. Also, he was pretty smug about that poker win.
Most redeeming moment: He saved Rose’s life at least three times. He also covered up her suicide attempt and made sure she was able to float on that door. Not to mention, he never lets go.
20. Danny Archer, Blood Diamond (2006)
What it’s about: Danny (DiCaprio), a former mercenary from Zimbabwe turned diamond smuggler, and Solomon (Djimon Hounsou), a fisherman from Sierra Leone, form an unlikely team in search of one particular pink diamond.
Biggest asshole move: Smuggling diamonds. And saying pretty dickish things to American journalist Maddy Bowen (Jennifer Connelly), who ends up being pivotal to his whole plan.
Most redeeming moment: He gives the diamond to Solomon and his son Dia (Kagiso Kuypers) and makes sure they get to safety, even though it means the end of his life.
19. Dominick Cobb, Inception (2010)
What it’s about: Cobb (DiCaprio) is a professional thief who gets into the subconscious minds of his targets as a corporate spy. He goes after the impossible task of inception, i.e., implanting someone’s idea into another person’s subconscious.
Biggest asshole moves: Stealing people’s dreams. And theoretically hurting some of them, including his wife Mal (Marion Cotillard), in the process.
Most redeeming moment: All he wants to do is get back to his children, and finally, at the end of the film, he does. (I think?)
What it’s about: Single mom Caroline Wolff (Ellen Barkin) thinks she finds a good man in Dwight Hansen (Robert De Niro), but her son Toby Wolff (DiCaprio) sees the true — and ugly — side to his stepfather-to-be.
Biggest asshole move: He fakes his grades to get away from his mom (Ellen Barkin)’s abusive boyfriend (Robert DeNiro). But really, who could blame him?
Most redeeming quality: He befriends a neighborhood boy who’s mocked for being effeminate. Not that he’s always nice to him (see above), but still.
17. Billy Costigan, The Departed (2006)
What it’s about: A young trooper (DiCaprio) who goes undercover with the Boston Irish mob, but soon realizes the situation is a bit more complicated.
Biggest asshole move: Sleeping with his boss’s girlfriend (Vera Farmiga). Of course, his boss, Sullivan (Matt Damon), turns out to be a mole within the Massachusetts State Police, but it’s not like Costigan knew that when the whole affair started.
Most redeeming moment: When he catches Sullivan and almost brings him in. If only he wasn’t killed shortly thereafter.
16. Frank Abagnale, Catch Me If You Can (2002)
What it’s about: An incredibly cocky New Yorker named Frank (DiCaprio) who cons his way into every single professional situation imaginable…and a helluva lot of money.
Biggest asshole move: Posing as a substitute teacher was just the start. He impersonates a doctor, a lawyer, and an airline pilot (stealing over $2.8 million from Pan Am), even convincing an FBI agent (Tom Hanks) that he is a member of the Secret Service. But probably the saddest lies are those he tells his poor fiancée Brenda (Amy Adams), getting her caught up in his mess.
Most redeeming moment: When he finds out his father (Christopher Walken) has died and, consumed with grief, returns home to find out he has a half-sister (Nathalie Baye). Realizing what he’s missed out on, he turns himself in. So, all’s well that ends well?
15. Richard, The Beach (2000)
What it’s about: A college student (DiCaprio) who looks for an adventure in Bangkok and finds himself on a dangerous island search.
Biggest asshole moment: He lures a French couple — Françoise (Virginie Ledoyen) and Étienne (Guillaume Canet) — with him onto the island and then has a passionate affair with Françoise. Also, he smothers a man to death whose leg becomes gangrenous. It’s a mercy kill, but murder is murder.
Most redeeming moment: When he completely loses it and starts hallucinating that he’s in a video game.
14. This Unnamed Kid Fighting Scout, The Outsiders (1990)
What it’s about: The orphaned Curtis brothers, who stick by each other’s — and their gang’s — sides, try to maintain their family unit when a welfare worker warns them that Ponyboy (Jay R. Ferguson) and Sodapop (Rodney Harvey) could be sent to foster homes.
Biggest dick move: He calls Scout (Heather McComb) a girl and then physically fights her. Low blow.
Most redeeming moment: None, but that’s only because we never see him again.
13. Jay Gatsby, The Great Gatsby (2013)
What it’s about: Nick Carraway (Tobey Maguire) rents a small home in Long Island’s West Egg, next door to mysterious businessman Jay Gatsby (DiCaprio), who holds legendary lavish parties at his humungous mansion. It turns out, the entire purpose of his parties was to reconnect with Nick’s cousin Daisy (Carey Mulligan), whom he dated five years earlier, though she’s now, unfortunately for Gatsby, married to Tom Buchanan (Joel Edgerton).
Biggest asshole moves: Trying to lure the married Daisy back into his arms, having an affair with her, telling her husband about said affair and letting Tom know that she never loved him, and then, being by Daisy’s side when she ran over Tom’s mistress Myrtle (Isla Fisher) and drove away. Oh, and, of course, lying about who he really was (a man born into poverty named James Gatz).
Most redeeming moment: He takes the fall for Daisy, which eventually costs him his life.
12. J. Edgar Hoover, J. Edgar (2011)
What it’s about: Hoover’s (DiCaprio) rise to power and his private life, including a romance with eventual FBI associate director Clyde Tolson (Armie Hammer).
Biggest asshole moves: Arranges to discredit Emma Goldman’s (Jessica Hecht) marriage to make her eligible for deportation; he also treats his lover Clyde like crap, emotionally, mentally, and physically; and he attempts to blackmail Martin Luther King Jr. into rejecting his Nobel Peace Prize with a letter threatening to expose his sexual life for no apparent reason.
Most redeeming moment: He was at the helm of the FBI’s investigation into the Lindberg kidnapping (and later, murder), which led to the arrest and eventual conviction of Bruno Hauptmann.
11. Andrew Laeddis, Shutter Island (2010)
What it’s about: U.S. Marshal Edward “Teddy” Daniels (DiCaprio) heads to Ashecliffe Hospital for the criminally insane on Shutter Island to investigate the disappearance of a patient named Rachel Solando, who’d been incarcerated for drowning her three children. Only later is so-called Teddy able to realize that he is actually Andrew Laeddis (for which Daniels is an anagram), having developed an alternative identity to suppress the reality of having murdered his wife (Michelle Williams), who drowned their three children.
Biggest asshole move: Murdering his wife.
Most redeeming moment: Doing it in the name of his children.
10. Amsterdam Vallon, Gangs of New York (2002)
What it’s about: A 19th-century New Yorker named Amsterdam Vallon (DiCaprio), who witnessed his father’s death at a young age at the hands of Bill “The Butcher” Cutting (Daniel Day-Lewis) and makes it his life’s goal to exact revenge upon him.
Biggest asshole moves: Stabbing Cutting to death and strangling Happy Jack Mulraney (John C. Reilly) to death. Though both were for arguably good reason (revenge and self-defense), as previously noted, murder is murder.
Most redeeming moment: He stands up for his black friend Jimmy Spoils (Lawrence Gilliard Jr.) against racism. Oh, and the fact that he does everything in the name of his father.
9. Romeo Montague, Romeo + Juliet (1996)
What it’s about: Shakespeare’s star-crossed lovers, told through the eyes of Baz Luhrmann.
Biggest asshole move: Killing Tybalt (John Leguizamo), Juliet’s cousin, who may have been an asshole himself, but again, it’s murder.
Most redeeming quality: He did it only after Tybalt murdered Mercutio (Harold Perrineau) and in the name of his love of Juliet (Claire Danes).
8. Hank, Marvin’s Room (1996)
What it’s about: When Bessie (Diane Keaton) finds out she has leukemia, she reconnects with her estranged sister Lee (Meryl Streep) and her family, including son Hank (DiCaprio), looking for a bone marrow donor.
Biggest asshole moment: He burned his mom’s house down (getting himself committed as a result) and later, runs away. He also pushes all men out of his mom’s life, but that’s secondary.
Most redeeming moment: He’s dealt with a lot a father-figure issues in his life, but still. At least he helps his Aunt Bessie learn to live a little.
7. Jim Carroll, The Basketball Diaries (1995)
What it’s about: Jim Caroll (DiCaprio) is on an incredibly successful high school basketball team, but off the court, his best friend Bobby (Michael Imperioli) is dying of leukemia. When Bobby dies, Jim’s life begins to unravel as his dependence on cocaine and heroin increases. And in order to pay for the drugs, he finds himself stealing, mugging, and prostituting himself.
Biggest asshole moves: He gets high on heroin and yells at his mom (Lorraine Bracco) about being a maid, he mugs an old lady on the street, and he sells out his friend when they hear the cops coming as they rob a diner.
Most redeeming moment: Visits Bobby as he is dying of leukemia and sneaks him out for a night at a peep show. Not classy, but well-intentioned.
6. Brandon Darrow, Celebrity (1998)
What it’s about: An unsuccessful writer (Kenneth Branagh) immerses himself in celebrity journalism following a midlife crisis and subsequent divorce from his wife (Judy Davis), finding himself in a world amongst models and actors, including Hollywood’s hot young thing Brandon Darrow (DiCaprio).
Biggest asshole moves: Beating up his woman of the moment and destroying a hotel room. Later, he invites Branagh’s Lee up to his hotel room for an orgy.
Most redeeming moment: He tells Lee that he’ll look at his script. Even though he’s full of shit, A for effort?
5. Derek, Don’s Plum (2001)
What it’s about: A group of guys meet up with a group of girls at a restaurant-bar called Don’s Plum.
Biggest asshole moves: Threatening a woman (Buffy’s Amber Benson) he just met and calling her a “cunt” and a “whore.” Considering DiCaprio, Kevin Connelly, Toby Maguire, Ethan Suplee, and Scott Blum, who all appear in Don’s Plum, were part of his ’90s circle of friends who allegedly dubbed themselves the “p***y posse,” it’s hard to separate this one from reality.
Most redeeming moment: He apologizes at dinner later to his bros for his behavior and also has a vulnerable moment in which he explains that his dad committed suicide. But five minutes later, he later calls Jenny Lewis from Rilo Kiley a “whore” and a “stupid bitch” when she rejects his attempt to have sex with her at the bar. Less redeeming.
What it’s about: A young couple, Frank (DiCaprio) and April Wheeler (Kate Winslet) move to a suburban home on a picturesque street in Connecticut, but soon, they begin falling apart.
Biggest asshole moves: He cheats on his wife, crushes her dream of moving to Paris, and chastises her for wanting an abortion, eventually leading her to perform one upon herself, which winds up being fatal.
Most redeeming moment: At least Frank devotes himself to his and April’s children after her death; as a neighbor notes, “Every spare moment he has, he spends with them.”
3. King Louis XIV, The Man in the Iron Mask (1998)
What it’s about: King Louis XIV (DiCaprio) has a secret twin brother who he’s kept imprisoned. Also, there’s some drama with the three musketeers.
Biggest asshole move: His public was starving and rioting so he told his chief of staff (Hugh Laurie from House!) to feed them rotten food. Then, he had him hanged for feeding the public rotten food. He also treated women horribly, and sent one of his musketeers’ sons, Raoul (Peter Sarsgaard), to war, where he died, so that he could move in on Raoul’s almost-fiancé.
Most redeeming moment: Nothing, unless you count his far nicer twin brother named Philippe.
2. Jordan Belfort, The Wolf of Wall Street (2013)
What it’s about: Queens-born Jordan Belfort is New York City stockbroker who quickly forms his own firm in the mid-’90s, Stratton Oakmont, thanks to securities fraud and corruption from selling penny stocks on Wall Street.
Biggest asshole move: Cheating on his first wife, Teresa (Cristin Milioti), with Naomi (Margot Robbie); cheating on Naomi with many a prostitute; dwarf-tossing (above) and thinking that little people would enjoy said activity; standing idly by while his friends and co-workers beat up his butler; becoming so incredibly dependent on cocaine and quaaludes; driving on “Lemon” quaaludes; basically raping Naomi and then punching her in the stomach; driving his young daughter while on cocaine and crashing; risking everyone’s life to save his own ass on his yacht, telling the captain to take them through a storm; being a generally misogynistic piece of shit; oh, and taking money from thousands of people who didn’t have it so that he could have more money than he knew what to do with.
Most redeeming moment: Maybe when he saves his best friend/co-worker Donny’s (Jonah Hill) life literally by giving him CPR. And maybe when he tries to save Donny’s life metaphorically by telling him he’s wearing a wire. Maybe.
1. Calvin J. Candie, Django Unchained (2012)
What it’s about: A freed slave named Django (Jamie Foxx) and the bounty hunter (Christoph Waltz) he hired go on a mission to rescue his wife (Kerry Washington) from cruel plantation owner Calvin J. Candie (DiCaprio).
Biggest asshole move: There is no bigger asshole than a n-word-dropping (check) slave owner (check) who makes his slaves fight to the death (check), but when Candie shows off his slave Broomhilda’s (Washington) whip-induced lashes on her back at a formal dinner, making her disrobe in front of his guests, he hit a low. And then, he hit an even lower low shortly thereafter when he nearly crushed her skull with a gavel after finding out her connection to Django.
Most redeeming moment: Though he doesn’t and couldn’t redeem himself, at least he gets shot shortly thereafter.