In the new movie Listen Up Philip, Jason Schwartzman stars as a young author named Philip Lewis Friedman. He’s unsympathetic to others, doggedly selfish, and emotionally cruel. Basically, he’s the type of total nightmare you hope to never get seated next to at a wedding, or God forbid, find married into your own family.

Friedman may be the most aggressively unappealing character that Schwartzman has ever played, but looking back at his film history, it’s remarkable and admirable how often he has portrayed loathsome characters. Typically this isn’t a route for an actor to become a star, but Schwartzman has been letting himself be shown in this light since he was 17 years old.

So, as Schwartzman reaches peak asshole with Listen Up Philip, let’s look back at some of the flawed figures and despicable zeroes he’s played over the years:

Rushmore (1998)

Who He Plays: Max Fischer. Though the character that made Schwartzman famous may be ambitious and endearing, for most of the movie you wouldn’t describe him as a nice kid. And that’s even before he’s expelled and things go to crap. Fischer may have saved Latin, but he also starts a rumor that his best friend’s mom gave him a handjob in the back of her Jaguar.

Facial Hair Situation: Adorably smooth-skinned.

Is He a Writer? Yes, he’s a playwriting prodigy, plus the president of the Calligraphy Club.

Are His Parents Dead? His mom is, but his dad is a barber, though Fischer tells everyone he’s a neurosurgeon.

Troubling Relationship With Women: “Although, I will say that Edward has more spark and character and imagination in one fingernail than Herman Blume has in his entire body.” —Rosemary Cross

“One dead fingernail.” —Max Fischer 

Slackers (2002)

Who He Plays: “Cool Ethan” Dulles. Schwartzman is the unicycle-riding creep who propels this terrible movie. It was his first major film role after Rushmore, and leading up to it, Schwartzman embraced the high-minded but reluctant young actor archetype during a Spin profile, which doesn’t quite jibe with the fact that Slackers is a movie that makes time for a peeing-in-the-shower gag right before its climactic confrontation. To his credit, Schwartzman really goes for it as Cool Ethan and gets some genuine laughs alongside a stacked list of supporting actors that includes: Jason Segel, showing why his high school nickname was Doctor Dunk! Michael Maronna, from The Adventures of Pete & Pete! Laura Prepon, masturbating! Jim Rash, with hair! Nat Faxon, as a grad school nerd! And Retta, as proto-Donna!

Facial Hair Situation: Clean-shaven, but his near-monobrow is an indicator of nuttiness. He also has the first letter of his infatuation’s name shaved into his chest hair.

Is He a Writer? Only of tortured ballads.

Are His Parents Dead? They’re never discussed, but there’s an unmentioned understanding that he probably murdered them.

Troubling Relationship With Women: He’s a stalker, so troubling relationships with women are kind of his bag. 

Spun (2002)

https://www.youtube.com/watch?v=DDjkl0wSn5o

Who He Plays: Ross. For his first starring role after Rushmore, Schwartzman went super dark as a tweaker battling both a crank addiction and bangs that always hang over his face.¹

Facial Hair Situation: Unkempt stubble.

Is He a Writer? Ross doesn’t seem capable of much besides driving Mickey Rourke around in a brown Volvo, leaving answering machine messages, and snorting speed.

Are His Parents Dead? There’s not a lot of backstory in this one, but Ross gets a message from his mom saying she’s planning to visit him. Unless she’s into hearing Rourke deliver filthy monologues in adult video stores or watching John Leguizamo shoot up, it’s going to be a bummer of a trip.

Troubling Relationship With Women: Early in the movie, Ross handcuffs a naked lady to his bed, then covers her mouth and eyes with duct tape before abandoning her for several days, just in case you had a shred of sympathy for his character. 

I Heart Huckabees (2004)

Who He Plays: Albert Markovski. Schwartzman acts as a stand-in for David O. Russell in this film from the director’s Berating National Treasure Lily Tomlin Era. Markovski is already ticking like an anxious time bomb at the start of the film, but after he hires a pair of existential detectives to investigate a coincidence, he explodes into a mess of neuroses and philosophical questing.

Facial Hair Situation: Consistently maintained light stubble.

Is He a Writer? He leads an environmental group, but his usual method of protest is expressed through his poetry. “You rock, rock.”

Are His Parents Dead? Nope, but his mother — played by Schwartzman’s actual mom, Talia Shire — is at the root of his problems.

Troubling Relationship With Women: Abandons his new best friend and supporter — played by a wild-eyed Mark Wahlberg in one of his top three performances — to have marsh sex with a nihilistic French existential detective.

Shopgirl (2005)

Who He Plays: Jeremy. An immature, aspiring typographer whose idea for a good first date is to take Claire Danes’s character to the tourist trap Universal CityWalk and tell her, “I like it here, it’s peaceful. I come here to think about fonts. I’ve actually been working on a font for you. It’s my most favorite.” Thankfully, Mark Kozelek later hires Jeremy as a roadie, turning him onto yoga and relationship advice CDs.

Facial Hair Situation: Scruff city.

Is He a Writer? No, but he tells Danes’s character he’s an artist within a minute of meeting her in a Laundromat, unprompted. Even worse?

Are His Parents Dead? Unknown.

Troubling Relationship With Women: More clueless than troubling, he accidentally grabs a mint instead of a condom the first time Danes invites him over to her place. Then, after he’s sent to the store to re-up, he instead just bums one from Danes’s neighbor. 

The Darjeeling Limited and the short Hotel Chevalier (2007)

Who He Plays: Jack. Schwartzman is the youngest of three brothers on an ill-conceived spiritual journey in India. Frequently barefoot and high on pain medication, he’s a seducer whose go-to move is to play Peter Sarstedt’s “Where Do You Go to (My Lovely)” on his iPod, which may be director Wes Anderson’s first cinematic acknowledgement of the digital world.² This character was Schwartzman’s first appearance in an Anderson film since Rushmore, and he’s appeared in every one since then. He also cowrote The Darjeeling Limited with his cousin Roman Coppola and Anderson.

Facial Hair Situation: Competent mustache, which he also used that year to play Ringo Starr in Walk Hard: The Dewey Cox Story.

Is He a Writer? Yes, of barely fictionalized fiction.

Are His Parents Dead? His father is dead, but Jack and his brothers are having trouble letting go of his Marc Jacobs–designed, safari print, overtly symbolic Louis Vuitton baggage.

Troubling Relationship With Women: Single-mindedly seduces the train’s stewardess, then accuses her of using him. Secretly checks on his ex-girlfriend’s phone messages while on a spiritual journey in India.

Funny People (2009)

Who He Plays: Mark Taylor Jackson, the self-obsessed star of the sitcom Yo Teach … !  He lets his stand-up comedian buddies, played by Seth Rogen and Jonah Hill, stay at his place, where he hangs his own portrait among photos of Bill Cosby, Rodney Dangerfield, and Chris Rock. As Hill’s character tells him, “Becoming marginally famous has really turned you into an asshole.”

Facial Hair Situation: Cultivated stubble, but his looks get compared to the notably smooth-faced Jackson Browne and Pete Rose.

Is He a Writer? Who needs writers when you’ve got the crack staff of Yo Teach … !?

Are His Parents Dead? Unknown, but his faux-soulful story about his grandfather’s death gets turned into a riff by Hill about the old man playing backgammon in hell with Hitler.

Troubling Relationship With Women: Considers playing a two-part episode of Yo Teach … ! on his computer a good way to hit on a girl.

Fantastic Mr. Fox  (2009)

Character: Ash. In Anderson’s stop-motion adaption of the Roald Dahl book, Schwartzman voices the son of the titular Mr. Fox. His spazzy ways confuse his unflappable father. He’s also able to unleash a Max Fischer–esque cruel streak, particularly on his naturally talented and kindhearted cousin Kristofferson.

Facial Hair Situation: Total fur coverage.

Is He a Writer? No, but his father is a columnist.

Are His Parents Dead? No, they’re the stars.

Troubling Relationship With Women: Responds with petty jealousy when his lab partner gets a crush on Kristofferson.

Bored to Death (2009)

Character: Jonathan Ames. The star of the HBO show that lasted three seasons, Schwartzman plays an often-stoned writer in Park Slope who starts out as a totally inept detective, but with experience becomes a moderately inept detective to get ideas for stories.

Facial Hair Situation: Keeps it clean.

Is He a Writer? Yep, it’s the premise of the show.

Are His Parents Dead? Nope, they are a delightful couple living in New Jersey.

Troubling Relationship With Women: He’s well meaning but can never keep a relationship going. Over the course of the show he gets together with an indie actress dream team that includes Jenny Slate, Parker Posey, Zoe Kazan, and Isla Fisher (whose character unfortunately turned out to be his half-sister). 

Scott Pilgrim vs. the World (2010)

Who He Plays: Gideon Graves. This is a return to a pure villain role as the chief baddie who puts together Ramona’s League of Evil Exes to defeat hero Scott Pilgrim, who Schwartzman potentially could have played five years earlier. Graves is the head of G-Man Records, “indie producer of the decade,” and owner of the Chaos Theatre, his “cathedral of cutting-edge taste.” Graves is Schwartzman at his smarmiest, a guy who plays nice like he just wants to be buds, but is actually a total dick.

Facial Hair Situation: Fresh-faced.

Is He a Writer? No, but I’m sure he has a great Tumblr page of money clips and vintage Bad Brains show fliers.

Are His Parents Dead? Unknown.

Troubling Relationship With Women: He’s pretty messed up. A deeply possessive boyfriend, he implants a mind-control device on ex-girlfriend Ramona Flowers so she’ll do whatever he wants. At one point he beats down Pilgrim’s ex, Knives Chau. 

Listen Up Philip (2014)

Who He Plays: Philip Lewis Friedman. The lead of the film, he decides at the beginning to no longer repress his emotions and now expresses every terrible thought in his head. A flashback reveals he wasn’t that fun to begin with.

Facial Hair Situation: Full-on beard. You’re a man now, Schwartzman!

Is He a Writer? He most certainly is.

Are His Parents Dead? Yes. You still don’t feel much sympathy for him.

Troubling Relationship With Women: He’s pretty shitty to every woman he interacts with in every nonphysical way you can imagine.

Eric Ducker (@ericducker) is a writer and editor living in Los Angeles.

1. It’s also music video director Jonas Akerlund’s hyper-stylized, deeply unpleasant film debut.

2. Don’t worry, there are still telegrams in this one.