This page details the characters in the HBO TV series Bored to Death.
The main character of the series, a 30-year-old struggling novelist living in Brooklyn. After his girlfriend dumps him due to his frequent substance use. Jonathan publishes a Craigslist ad describing himself as an (unlicensed) private detective.
- The Alcoholic: Often downplayed in favor of his marijuana use, but Jonathan drinks white wine very, very frequently.
- Amateur Sleuth: Jonathan becoming one of these out of boredom and loneliness is the show's premise.
- Apologises a Lot: This is pointed out by Sarah Silverman's therapist character when Jonathan is in deep water with George.
- Author Avatar: Shares a name with the creator of the show, and many of the misadventures show-Jonathan gets himself into were inspired by incidents from the real Ames' memoirs.
- Clueless Detective: Especially in the first season, most of Jonathan's cases go horribly wrong.
- Crouching Moron, Hidden Badass: It's very, very hidden, but this is visible in the rare instances when Jonathan actually succeeds in solving something, especially after bribing people.
- Disguised in Drag: Briefly, when he's attempting to solve a case at a Korean spa and must go into the women's locker room.
- Extreme Doormat: Jonathan is prone to spirals of self-loathing, gets kicked around all the time, and Apologises a Lot. George points this out during their feud.
- Gag Nose: The size of Jonathan's nose is frequently the butt of jokes.
- Heterosexual Life-Partners: With both George and Ray.
- Hollywood Dateless: He tends to complain about being lonely, but he encounters a new Girl of the Week in almost every episode.
- Jewish and Nerdy: Constantly pointed out by other characters. He's described as "one of those self-hating New York Jews" within the first minute of the pilot.
- Mistaken for Gay: Often happens when he's out and about with Ray.
- Not-So-Badass Longcoat: Jonathan tries, but he can't really pull off a Badass Longcoat.
- Serial Romeo: He's instantly attracted to nearly every woman he runs into.
- The Stoner: Much like the other two leads, Jonathan constantly smokes marijuana.
George is the editor of New York magazine Edition. In addition to being his occasional employer, he's become a close friend and father figure to Jonathan, perhaps as a way to vicariously reclaim his youth (often through drugs and sex) and to escape boredom.
- Bourgeois Bohemian: George runs an upper-class magazine similar to The New Yorker and constantly smokes pot. A major plotline in Season 2 involves him adjusting to the fact that his magazine is bought by a conservative company.
- Cool Old Guy: Desperately wants to be one, after spending decades in the New York corporate world.
- The Dandy: He's intensely concerned about his appearance. One episode involves a herpes scare on his lip, which he's horrified about.
- Divorce Is Temporary: He hooks up with his ex-wife Priscilla several times throughout the series, claiming he never fell out of love with her.
- Eccentric Mentor: To both Jonathan and Ray.
- Erudite Stoner: He has his clueless spirals, but George serves as a (comparatively) wise mentor to Jonathan even while stoned out of his mind.
- Literal-Minded: When Ray says that the all male changing rooms at a Korean spa are an "Asian sausage factory," George marvels at how a spa also produces Asian sausage and notes that he would like to try one sometime.
- Parental Substitute: Serves as a father figure to Jonathan more and more as the series goes on.
- Really Gets Around: While at a bar with Jonathan, he starts counting all his past one-night stands and comes to the realization that he's been "fucking forever." He's also been married thrice.
- Sharp-Dressed Man: He's always wearing fancy suits.
- Sophisticated as Hell: As part of his high-class nature, George talks in a grandiose manner and often spouts out obscure literary references in addition to his liberal amounts of swearing.
- The Stoner: George has been smoking weed since the 1960s.
- The Wonka: He's a bigwig in the publishing world, and also a deeply strange man, bordering on Manchild.
Ray, a rather curmudgeonly comic book artist, is Jonathan's best friend and sidekick who often accompanies him in his cases. In his own life, he's dealing with financial difficulties and volatile relationship issues with his on-and-off girlfriend Leah.
- Did Not Get the Girl: The series ends with Leah conclusively breaking up with Ray.
- The Drag-Along: He really wants nothing to do with most of Jonathan's cases, but is a loyal enough friend to stick with him.
- Gag Penis: His comic book alter-ego, "Super-Ray," whose massive penis is the source of his powers.
- Heterosexual Life-Partners: With Jonathan, and also George later on.
- It's All About Me: He and Leah are both very self-absorbed in ridiculous ways, which causes a lot of their arguments.
- Kavorka Man: Especially once his comics start selling, Ray gets a strange amount of attention from women despite being a slovenly, pudgy, immature man.
- Kids Are Cruel: He's apprehensive to meet his son Spencer (the result of his sperm donor) because kids bullied him constantly, calling him "Gay Hueston."
- Likes Older Women: Toward the end of the series, he realizes he's suffering from "elder love."
- Manchild: To a ridiculous extent. He can barely function as an adult and is well aware of this:"I should have never started dating a woman with kids. I have to be the only child in a womans life."
- Mistaken for Gay: He and Jonathan are assumed to be a couple multiple times, and then there's his strange dynamic with Louis.
- Relationship Revolving Door: Ray and Leah break up and get back together countless times.
- The Stoner: He smokes perhaps even more than Jonathan, claiming it's the only way he'll get artistic inspiration.
- Unsympathetic Comedy Protagonist: Ray is a selfish man-child with an infantile obsession regarding his penis (basically the centerpiece of his web comic), who mooches off his girlfriend, cheats on her with an older woman at one point, and is often intoxicated when he is supposed to be watching her children or his infant son.
- It's All About Me: Although it's in a more (seemingly) adult-oriented manner than Ray.
- On the Rebound: Immediately after dumping Ray, Leah hooks up with another man named Irwin (played by the real Jonathan Ames in a full-frontal nude cameo).
- Parenting the Husband: Ray often childishly bemoans how she makes him do chores, gives him an "allowance," and usually has to "reward" him with sex.
- Relationship Revolving Door: Ray and Leah break up and get back together countless times.
- The Smurfette Principle: After Heather Burns was promoted to the main cast in Season 2, Leah is the one main female character in the series and has little depth outside of her relationship with Ray.
- Tiny Guy, Huge Girl: Leah is considerably taller than Ray, even if he's pudgier.
- Women Are Wiser: Subverted: while Leah clearly has her life together much more than Ray, her actions are just as bizarre.
- Always Someone Better: He tries to one-up George in any way possible, whether in a boxing match or opening a rival restaurant.
- For the Evulz: There's no real reason he keeps screwing with George, he just seems to enjoy it.
- HeelFace Turn: Strangely, at the end of "Make It Quick, Fitzgerald!", a dejected Richard (who just discovered his wife is cheating on him with George) asks George and Jonathan if they want to grab a drink. He's back to his usual self in the next season, however.
- Large Ham: He's obnoxious and blustering, especially when preparing for his boxing match against George.
- Last-Name Basis: George only refers to him as "Antrem."
- Properly Paranoid: He has very little reason to believe Priscilla is having an affair when he hires Jonathan. She is having one, and with Georgewho is also Antrem's nemesis and publishing rivalto boot.
- Sitcom Arch-Nemesis: To George, naturally. Cranked Up to Eleven in Season 3 when after George opens a restaurant, Richard opens his own restaurant specifically to try and drive George's out of business.
- Smug Snake: He's got far more of an ego than George.
- Ugly Guy, Hot Wife: George is deeply offended that the "pompous, bloated toad" Richard is married to his "favorite ex-wife" Priscilla.
- Ambiguously Gay: He suddenly kisses Ray the one time Ray appears to express sympathy for him. Later in that episode, he admits he's deeply lonely and intimacy-starved. There are no real hints to his sexuality otherwise.
- Complaining About Rescues They Don't Like: After he sprains his ankle and Jonathan rescues him from a mob of angry drug dealers.
- Freudian Excuse: According to Richard, his father was a childhood psychologist who experimented on him and made him sleep in a box.
- Humiliation Conga: In Season 3, Louis has crippling debt, is bumped from the Dick Cavett Show which he has spent his entire life wanting to appear on, gets arrested, and winds up working a menial job for Richard, who constantly berates him.
- Insufferable Genius: Starts out as one, then becomes more of a Small Name, Big Ego as the series goes on.
- Laser-Guided Karma: Louis's segment on The New Dick Cavett Show is canceled in favor of Jonathan's. The revelation causes him to go through serious Sanity Slippage.
- Sesquipedalian Loquaciousness: To accentuate his smugness, he talks in a ridiculously flowery fashion.
- Sitcom Arch-Nemesis: To Jonathan, clearly. It's never fully explained why he hates him so much.
- Smug Snake: Mostly everything he says is dripping with condescension.
- Villain Decay: After his arrest on the Dick Cavett Show, Louis becomes less threatening and more of a sad sack.