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July 13, 2018 at 10:00 AM EDT

Once pigeonholed as a comedy star, Jonah Hill has proven himself to be a serious and gifted actor who can tackle meaty roles in talent-filled films — two of which, so far, have earned him Oscar nominations.

His latest dramatic role, Gus Van Sant’s Don’t Worry, He Won’t Get Far on Foot, stars Hill as Donnie, AA sponsor to quadriplegic alcoholic cartoonist John Callahan (Joaquin Phoenix), on whose memoir the film is based. Donnie will break your heart — but that’s what we’ve all signed up for, isn’t it?

In recognition of Hill’s ongoing career shift (and this latest step in it), we’ve ranked six of his best dramatic roles from mildly affecting to downright tearjerkers. Read on to see which of his sentimental turns takes the top spot.

(Vague spoilers below.)

HAIL, CAESAR (2016)

Hail, Caesar might not be an actual drama, but it still qualifies as part of this trend in Hill’s filmography if only because it’s a Coen Brothers movie. Even though it’s a hilarious comedy populated by a star-studded ensemble that satirizes and celebrates classic Hollywood, it’s still got a strong undercurrent of existential dread. Hill plays a dorky financier who connects with Scarlett Johansson’s synchronized-swimming starlet. Nothing heartbreaking about that!

HEARTBREAK RANKING: Zero!

MONEYBALL (2011)

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Bennett Miller’s Moneyball tells the improbably thrilling true story of how math saved baseball, and Jonah Hill plays the nerdy accountant who figured it all out. It does not rank as happiest on the sad-o-meter only because it is technically a sports movie, and all sports movies are at least a little bit heartbreaking, because they are about games of physical endurance and teamwork as a metaphor for Life — even when they are also about math.

HEARTBREAK RANKING:

WOLF OF WALL STREET (2013)

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Hill plays partner-in-crime (literally) to Leonardo DiCaprio’s real-life corrupt stockbroker Jordan Belfort in Martin Scorsese’s profane dark comedy. Friendships can be heartbreaking, but these two sociopaths’ fraught relationship isn’t what moves us most about this. No, our hearts break for America! America, in all of its excess, avarice, and depravity!

HEARTBREAK RANKING: 💔 💔

WAR DOGS (2016)

Hill starred alongside soon-to-be-mini-Goose Miles Teller as a pair of friends who become arms dealers in Todd Phillips’ dark comedy-drama. Our hearts break for Teller’s character, who tries to do the right thing and support his family, but falls victim to the manipulations of a manic, greedy Hill. Our hearts also break for America again. Obviously.

HEARTBREAK RANKING: 💔 💔 💔

TRUE STORY (2015)

Rupert Goold’s True Story chronicles the strange (but true) story of an accused murderer (James Franco) who stole the identity of a journalist (Hill) and then forged a bizarrely powerful friendship with him. It’s heartbreaking to begin with that Franco’s character viciously murdered his wife and children. Our hearts break too, however, to see his manipulations slowly tear Hill’s character’s life apart.

HEARTBREAK RANKING: 💔 💔 💔 

DON’T WORRY, HE WON’T GET FAR ON FOOT (2018)

Scott Patrick Green/Amazon Studios

Don’t worry, you probably won’t get far into this movie before bursting into tears. Hill’s Donnie is a gentle and loving soul who has suffered profoundly, but come out on the other side filled with love and hope for other people. Major heartbreak alert!

HEARTBREAK RANKING: 💔 💔 💔 💔 💔

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