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High School Acquaintances

    The Waitress 

The Waitress

https://static.tvtropes.org/pmwiki/pub/images/sunny_waitress.png
"Really, Charlie, will I marry you? No, no I will not. I will never marry you."
Played By: Mary Elizabeth Ellis

The object of Charlie's affections. Initially employed at a coffee shop near Paddy's, the Gang's meddling causes her to lose several jobs across the series.


  • The Alcoholic: She claims to have a drinking problem. She seems to have it in check, but the few times she slips up, she really goes overboard.
  • All Girls Want Bad Boys: Despite knowing what a scumbag Dennis is, there are times where she ignores all common sense and still finds herself pining for him. She always winds up coming to regret it, yet the lesson never sticks.
  • Boyish Short Hair: Sports this on and off across her appearances.
  • Break the Cutie: Thanks to the Gambit Pileup in "Mac Bangs Dennis' Mom".
  • I Can't Believe a Guy Like You Would Notice Me: She eventually asks Charlie why he's so obsessed with her when there are far better people out there. He responds that for him, there is no one better. This actually gets her to sleep with him.
  • Characterization Marches On: Much like Dee, the Waitress used to be the Only Sane Man to the Gang's antics. Then she developed an obsessive crush on Dennis, started drinking again, and became more and more of a Butt-Monkey.
  • The Chew Toy: The Waitress tends to be easily manipulated by the Gang, and generally suffers in some shape or form whenever she appears.
  • Everyone Calls Him "Barkeep": Everyone calls her "the Waitress," even her stalker Charlie and the guy she was engaged to.
  • Forgettable Character: Only Charlie remembers her from high school, and no one, not even Charlie, can remember what her name is.
  • Forgotten Childhood Friend: While she was never the Gang's friend, she went to high school with them for all four years, and shared several classes with most of them. Despite this, all of the Gang but Charlie tend to forget ever knowing her outside of being a waitress.
  • From Bad to Worse: Employed much more subtly than with Cricket. As she continues to appear her living situation gets substantially worse, with her falling into alcoholism and drug addiction. By her latest appearance she is living in a women's shelter. Interestingly, she is one of the few characters whose declining life can't be directly tied back to the Gang (though they certainly haven't been helping her), and it's suggested her problems are mostly her own.
  • Love Martyr: For Dennis, but much less pronounced than Cricket is for Dee. She is extremely forgiving of all of the horrible things he's done to her in the past if it means starting a relationship with him.
  • No Name Given: Lampshaded on a few occasions. At the high school reunion it is implied her name is Nikki Potnick, but Word of God has confirmed it isn't.
  • The Nondescript: No one can remember her name, and no one except Charlie remembers her from high school, to the point of the school forgetting to make her a name tag for the reunion.
  • Not So Above It All: Can be just as rude and cynical as the Gang at times. "Flowers for Charlie" also suggested she is as vapid and shallow as them too.
  • Not So Different: Later episodes heavily suggest her to be just as cruel, shallow, stupid and vapid as the Gang, but too self-important to acknowledge it. Ironically, this makes her one of the few people worse off than the Gang, as while they at least have each other as dysfunctional True Companions, the Waitress is completely alone.
  • Really Gets Around: Which makes it all the more ironic that Charlie still hasn't had sex with her. Until the season twelve finale, that is.
  • Sixth Ranger: Plays a completely unwilling one frequently.
  • Sleeps with Everyone but You: The Waitress will sleep with just about anybody except for Charlie. At least, up until "Dennis' Double Life".
  • Stalker with a Crush: A recipient of this from Charlie. Sometimes acts this way herself, to Dennis.
  • The "The" Title Confusion: When explaining to Dennis that she doesn't use the internet at all, she says that she doesn't "do, like, the emails."
    Dennis: "The emails"?! It's "email"! It's just "email"!
  • Two Decades Behind: Uses a cell phone that looks like it came from the late 90's and doesn't use or understand anything about the internet.
  • With Friends Like These...: Dee occasionally claims that she's her best friend. Not only does the Waitress hate her guts, but Dee only spends time with her when she has something to gain.
  • You Are What You Hate: Hates the Gang despite essentially being no different from them.
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    Rickety Cricket 

Matthew "Rickety Cricket" Mara

https://static.tvtropes.org/pmwiki/pub/images/cricket_season_11.jpg
"You want to hear about a dog orgy or when a cat bit off my toe?"
Played By: David Hornsby

Former high school classmate of Dennis, Dee, Mac, and Charlie. A Roman Catholic priest who becomes defrocked, destitute, abducted, assaulted (both non-sexually and sexually), threatened, hunted, severely injured and addicted to cocaine all directly or indirectly resulting from the influence or action of The Gang. As a boy he suffered from a medical condition that required the use of very conspicuous complex leg braces which inspired the pejorative nickname "Rickety Cricket".


  • Alliterative Name: Though no one calls him Matthew Mara. His nickname almost rhymes.
  • All Love Is Unrequited: For Dee, although God knows why.
  • Anything That Moves: By season 11 it is clear he has come to mostly enjoy the sexual depravity he experiences. He brags about being in a "dog orgy" and casually elaborates on the favours he will perform on men in exchange for drugs and alcohol.
  • Beard of Sorrow: Steadily grows a mangy beard as he deteriorates.
  • Bestiality Is Depraved: Season 11 has him gloat about being a part of "dog orgies". "A Cricket's Tale" has him make out with a dog he hallucinated as a human woman.
  • Black Comedy Rape: His most recent appearances have him frequently mention the countless times he's been assaulted while living on the streets, by both humans and non-humans alike. Played with in that it's treated as being legitimately gross and disturbing in-universe, with Charlie even telling him at one point to stop talking about how often he gets raped.
  • Break the Cutie: He goes from a clean-cut, mature, and successful priest to a crack-addicted street rat who has lost his mind. All thanks to Dee.
  • Butt-Monkey: Poor Cricket has fallen to the very bottom of society's rung, and then a few rungs below that, thanks to the Gang.
  • Card-Carrying Villain: By the later seasons he's been completely corrupted, to the point where he gladly dresses like a terrorist and blinds the Gang in a fight in the name of destroying America.
  • Character Development: While he's definitely become much, much worse after spending so much time with the Gang, he at least seems to have finally gotten over Dee. He's also steadily Stopped Caring about his quality of life, causing him to go from viewing the Gang as his hated enemies to his only friends and generally acting much more zen than in the past.
  • The Chew Toy: Every season, he suffers from progressively worse injuries, from getting the side of his his throat slashed, to getting shot, to getting half his face burned off.
  • Crazy Homeless People: Began to fill the stereotype more and more as time went on. After that reached its peak, he has started to become more deranged and animalistic.
  • Crouching Moron, Hidden Badass: The few times he physically confronts the Gang, he kicks their asses. He still always ends up getting screwed over though.
    • He also shows off some incredible parkour skills in "A Cricket's Tale," effortlessly descending a fire escape without touching a single step and landing a perfect front flip from the top of a garbage truck.
  • Cyborg: Parodied. After he acquires a new set of high tech leg braces, the Gang constantly marvels about how he has become "half machine".
  • A Day in the Limelight: Season 12's "A Cricket's Tale" revolves entirely around him.
  • Descent into Addiction: The Gang got him hooked on cocaine, and later to meth, crack, and PCP. While he no longer cares about Dee, the Gang can still manipulate him into helping them simply by offering him drugs or a beer.
  • Dogged Nice Guy: He doesn't like Dennis, Mac and Charlie at all and only helps the Gang out to try and win Dee's heart. He seems to have finally gotten over this, as he acknowledges that she's a total bitch multiple times and no longer seems to care about her.
  • Eye Scream: In Season 8, he's lost one of his eyes. The most surprising thing about this is that this wasn't the Gang's fault for once.
  • Facial Horror: The first time we see him in Season 8, he has a scar over his eye, which he got from an off-screen incident that was, for once, entirely his fault. After his fate in "The Gang Squashes Their Beefs," he now looks like Two-Face.
  • Fate Worse than Death: Every time you think he's going to be Killed Off for Real, he gets a severe injury instead.
  • Friendly Enemy: He's become so broken and used to the Gang screwing him over that he's generally pretty nonchalant and even friendly with them in his later appearances, even cheering them on in "The Gang Goes on Family Fight". In "A Cricket's Tale", he even openly calls the Gang his friends.
  • From Bad to Worse: No matter how low he has sunk, the Gang always seems to manage to make his life even worse. At this point, expect every appearance to cost him a body part.
  • Good Shepherd: Was this, until Dee managed to get him to renounce his faith and thus lose his job. He ended up on the streets and his life has only gotten worse from there.
  • Got Volunteered: The Gang always recruits him to perform work that not even Charlie is willing to do. In the earlier seasons, they'd do this by tricking him. In the later ones, he's willing to do whatever so long as he gets a can of beer.
  • He Cleans Up Nicely: He shows up to his high school reunion clean-cut and composed, apparently having been let back into the priesthood. Even after all that had happened to him up to that point, he still looks quite handsome. It turns out to have been a ruse, though. However, starting with Season 8, he has been getting horrific injuries that he will probably never be able to recover from.
  • Heel–Face Revolving Door: While calling the Gang faces is probably going too far, Cricket swaps between being their ally and enemy constantly, generally several times an episode.
  • Humiliation Conga: Has been in a perpetual one for most of his life, courtesy of the Gang.
  • Love Martyr: For Dee.
  • Mutilation Conga: Most of his appearances end with him getting an injury, the severity of which varies depending on the episode.
  • No Accounting for Taste: His crush on Dee remains despite innumerable amounts of evidence that she hates him and is a terrible person. Seems to have finally wised up to this, but by that point he's already lost his job, his house and his mind because of her.
  • Only Known by Their Nickname: The Gang exclusively refers to him as either "Rickety Cricket", "Cricket", "Cricks", or "Street Rat". The number of times his real name is mentioned can be counted on one hand. The Gang doesn't actually seem to know what his real name is, as when he introduced himself as "Matt" early on, none of them were able to recognize who he was. By the later seasons, Cricket himself seems to have embraced the name Cricket, suggesting that he's completely abandoned his previous identity as Matthew Mara.
  • Running Gag: See The Chew Toy and Mutilation Conga above.
  • Sanity Slippage: Goes from the Only Sane Man in his first episode to one of the Gang's most deranged acquaintances by his later appearances. It's almost hard to believe he's the same character.
  • "Shaggy Dog" Story: He was relentlessly bullied for wearing leg braces as a teen before cleaning himself up and becoming a respected priest... after which he ends up losing his job and being put into a much, much worse situation than he was initially with no hope of recovery and, as a final insult, stuck in leg braces once again.
  • Sixth Ranger Traitor: The Gang frequently ropes him into their schemes, but he's just as likely to betray them.
  • Squick: In-universe. His eagerness to recount his sexual encounters begins to freak out the Gang after a while.
    Cricket: You have to fake. The guys that don't fake — they're the ones that get it the worst.
    Charlie: Cricks, like anything we can do to have you not talk about sucking penises or getting raped in the butt?
  • Stockholm Syndrome: While he's initially hostile to the Gang (even Dee, after a while) for ruining his life, by the later seasons he's become so broken and used to them roping him into their schemes that he now considers them to be his only friends and generally shows none of his previous wariness around them.
  • Stopped Caring: After leaving the priesthood, he was initially desperate to do whatever he could to get off the streets. After devolving further into being a street rat, he turned his sights towards getting revenge against the Gang for ruining his life. Currently, he's fallen so far that he no longer cares about rejoining the priesthood or getting revenge on the Gang, and is content to accept whatever horrors life throws him so long as he gets the occasional booze and drugs.
  • That Man Is Dead: To go along with his Sanity Slippage and gradual lack of interest in reclaiming his old life, he has largely abandoned his identity as Matthew Mara. "A Cricket's Tale" cements this, as he finds himself incapable of completely reacclimating himself to going back to living an ordinary life in it.
  • Unlucky Childhood Friend: Again, for Dee.
  • With Friends Like These...: By the later seasons, he's come to accept the depraved and pathetic life of a street rat and now considers the Gang to be his friends, causing him to act much more cordially towards them. Despite this, the Gang can't even be bothered to learn his real name, only ever contact him when they need to manipulate him and are openly disgusted by his lifestyle despite being the sole cause of it.

    Bill Ponderosa 

Bill Ponderosa

https://static.tvtropes.org/pmwiki/pub/images/sunny_bill_ponderosa.jpg
"I spiked the milk with methylenedioxypyrovalerone. It's bath salts.".
Played By: Lance Barber

Dee's high school crush and the brother of Dennis' high school girlfriend Maureen Ponderosa. He has put on a lot of weight since high school and has grown into an awful and hedonistic man.


  • Abusive Parents: Flat out told his son that he doesn't love him, and told his daughter she "was too fat to be a slut". Neither of them seem older than 12.
  • Affably Evil: Bill is a very jovial fellow who's always willing to share his drugs with people... who don't want his drugs. Bill cheats on his wife, frequents prostitutes, snorts up whatever drug is closest and lies to women that he had a vasectomy to avoid wearing a condom. Even the Gang find him super shady.
  • Beard of Evil: Sports a beard in his later appearances and is in the running for biggest scumbag in the series. May overlap with Beard of Sorrow since he's suicidal.
  • Birds of a Feather: Gets along better with fellow hedonist Frank than he does any other member of the Gang.
  • Death Seeker: Has casually tried to kill himself multiple times.
  • Fat Bastard: Was in pretty good shape in high school, but has gained a lot of weight since. Plus he's a bastard.
  • Formerly Fit: He was handsome as a young man, but is now sleazy and overweight.
  • The Friend Nobody Likes: While he's consistently one of the more pleasant supporting characters towards the Gang, Frank is the only one who isn't completely disgusted by him.
  • Functional Addict: He appears pretty well-adjusted upon first meeting him, and then he starts casually using drugs.
  • Future Loser: Was apparently rather handsome and popular in high school, but is currently an overweight alcoholic and one of the few people who may even surpass the Gang in sheer awfulness.
  • The Hedonist: Gluttony, lust, drugs. Yep, sounds about right.
  • In-Series Nickname: Frank starts calling him "Pondy" by the later episodes.
  • I Was Quite a Looker: He was attractive enough for Dee to crush on him back in school, but is now fat and gross.
  • Jerkass: He's a horrible person all around, and lacks even the faintest hint of any sympathetic traits.
  • Suicide as Comedy: Although he's yet to go through with it, he was seriously threatening to kill himself at the thought of being the father to Dee's baby and has attempted to drink himself to death.
    Dennis: What are you celebrating, Bill?
    Bill: I'm gonna kill myself! Yeah, I botched it — life, you know?
    • By his later appearances, his first instinct at the sight of trouble is to try and kill himself, with the Gang being the only things stopping him from going through with it.
    [Bill is chased out of children's establishment by group of angry fathers, rushes to his car, and pulls a gun out of the glove box]
    Bill: (to Frank) Somebody's gonna die today! [puts gun to own head]
    Frank: Pondy no!!
  • Toxic Friend Influence: A mutual example with Frank. He ensures that Frank continues to sink into kinds of depravity that the Gang are incapable of doing while Frank (his AA sponsor) makes sure that Pondy never gets his life together.
  • Your Cheating Heart: Cheats on his wife with several prostitutes and Dee.

    Maureen Ponderosa 

Maureen Ponderosa

https://static.tvtropes.org/pmwiki/pub/images/sunny_maureen_ponderosa.jpg
"I like to be comfy and current."
Played By: Catherine Reitman

Dennis' high school girlfriend and ex-wife, and the sister of Bill Ponderosa. Known for her foul-smelling dead tooth and obsessive personality. Following their divorce, she has spent all of Dennis' alimony checks on frivolous surgeries for herself.


  • Abhorrent Admirer: When she's not tormenting Dennis she's usually trying to get back together with him.
  • Crazy Cat Lady: Literally. Her obsession with cats has evolved to a point where she has had multiple surgeries to make herself look like one.
  • Cute and Psycho: She's an attractive lady, but she's also incredibly mentally unstable.
  • Fourth Date Marriage: Played With. She and Dennis knew each other in high school. They met up again, now older. They have one more date before getting married. Dennis falls out of love with her the next day.
  • Gag Boobs: Uses some of Dennis' alimony checks to give herself breast implants, which end up drawing a lot of focus from other characters. As she begins transitioning into a cat, however, she ends up getting the silicone in her breasts moved to her cheeks to make her face look more cat-like.
  • Killed Off for Real: Breaks her neck and dies falling off of a rooftop before the beginning of "Making Dennis Reynolds a Murderer".
  • New Old Flame: Dennis' sudden remembrance of her brings out an uncharacteristic amount of nostalgia in him, which pushes him into reconnecting with her. Of course, he comes to regret doing so immediately afterwards.
  • Not So Different: At first she seems like a perfectly sweet girl, as opposed to her evil brother. However, she gradually becomes just as unhinged as he is albeit in a different way.
  • Petting Zoo People: The running gag of her using Dennis' alimony payments for unnecessary cosmetic surgeries ends up with her trying to turn herself into a cat.
  • Psycho Ex-Girlfriend: A classic example to Dennis, though in this case she's his ex-wife.
  • Sanity Slippage: It's unclear what began to send her down the path of insanity, but she's firmly down that yellow brick crazy road. It's likely it began with her discovery of her father's corpse after he committed suicide, and from there on she grew increasingly unhinged by she starts thinking herself as cat.
  • Trans Nature: Starts identifying as a cat later on, to the point of demanding that others treat her like one, and making feline noises during serious conversation:
    The Lawyer: Maureen, you are the sister of Bill Ponderosa, and it was at your wedding that Liam got attacked?
    Maureen: Meow.
    Lawyer: Your Honor, nothing represents the tragic aftermath more than the dramatic transformation of this woman.
    Maureen: Cat.
    Lawyer: ... excuse me?
    Maureen: As I transition from woman to cat, I must insist on being referred to as a cat.
    Jack: Objection. She's not a cat, Your Honor.
    Maureen: [hisses aggressively at Jack]
  • Yandere: Randomly switches between loving and hating Dennis.

    Schmitty 

Peter Schmidt AKA Schmitty

https://static.tvtropes.org/pmwiki/pub/images/sunny_schmitty.jpg
"What's going on? You guys gonna try to bang me or something?"
Played By: Jason Sudeikis

A former member of the Gang from back when they were in high school. Mac and Dennis kicked Schmitty out of the Gang (and a moving car) to make Charlie happy. Charlie and Schmitty used to be roommates and Charlie always feels upstaged by Schmitty.


  • The Ace: Schmitty is good at a lot of things, though this is really only in comparison to the Gang.
  • A Lighter Shade of Black: Schmitty would be a pretty stereotypical "asshole friend from high school all grown up" character if it weren't for the fact that the Gang are all infinitely worse than him in every possible way. As a result, Schmitty actually comes off as both the Token Good Teammate and The Ace when alongside them.
  • The Bully: Part of Charlie's hatred of him stems from his tendency to aggressively make fun of him and then playing it off as just him joking around. He does this to the rest of the Gang as well, but they all think he's cool for doing it.
  • Handsome Lech: Schmitty's a handsome guy, but seemingly gets most of his action from preying on women who are too drunk to know better.
  • Jerkass: Generally comes off as an obnoxious dude bro who constantly picks on others under the guise of "just kidding around". Unlike the Gang, though, he's just a jerk, and is distinctly put off by their usual behavior.
  • Only Sane Man: For the short time when he returns to the Gang. He's very quickly put off by their strange habits and rituals, to the point of telling them outright how weird he thinks they all are.
  • Token Good Teammate: Only in comparison to the Gang. He's smug, tends to casually bully his friends, and, as shown in "The High School Reunion", acts predatory towards women by taking advantage of them when they're drunk. Despite this, the Gang is just so terrible, that Schmitty almost manages to come off as a paragon of virtue in the brief instance when he rejoins them.
  • Unknown Rival: Charlie hates him and considers him a threat to his position within the team, but Schmitty seems oblivious.

    Fatty Magoo 

Ingrid "Fatty Magoo" Nelson

https://static.tvtropes.org/pmwiki/pub/images/sunny_fatty_magoo_9.png
"Hey, do you remember how you used to say that you were gonna be famous and have your own clothing line?"

Played By: Judy Greer

A high school friend of Dee's. In high school, Dee wore a back brace and was dubbed the Aluminum Monster while Ingrid was morbidly obese and was given the name Fatty Magoo. As an adult, she lost all of her excess weight and has become a successful dress designer.


  • Earn Your Happy Ending: She was highly unpopular in her teens, but became gorgeous and successful in adulthood. She's also one of the few people in the series who hasn't had her life ruined by the Gang (yet).
  • Formerly Fat: The reason her nickname in high school was "Fatty Magoo."
  • Good Counterpart: She's similar to Dee in that they were both mocked in high school only to become attractive after graduating, but rather than stew in rage over her awful high school experience and cling to the past, she chooses to move on and become a happy and successful person.
  • Meganekko: Ingrid is a very attractive woman who wears glasses.
  • Nice Girl: She maintains a cheerful disposition. When Dee told her that she herself was gonna grow up to be an actress to rub it in her face, it instead inspired Ingrid to run her own clothing store. And she personally thanks Dee for this upon seeing her in her store.
  • Non-Indicative Name / Ironic Nickname: "Fatty Magoo" has since become one, as she is now thin and beautiful. Since the Gang are all childish idiots, though, they still exclusively refer to her by it.
  • Only Known by Their Nickname: The Gang never once calls her by her real name, despite it now longer making sense when applied to her.
  • She's All Grown Up: A fat, shy and awkward girl in high school, she is now thin, confident, mature and successful as an adult. This is highlighted in "The Aluminum Monster vs. Fatty Magoo", where, though both she and Dee have become outwardly more attractive since high school, it is her mental maturation that is the true secret to her success.
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    Psycho Pete 

Peter AKA Psycho Pete

https://static.tvtropes.org/pmwiki/pub/images/sunny_psycho_pete.jpg
"Uh... dude, that was psycho... I-I don't feel good about that stuff."
Played By: Dominic Burgess

A high school friend of Mac and Charlie and leader of their gang "Freight Train". The two saw him as a harmless Cloudcuckoolander, but Ingrid Nelson tells them that he is in an asylum for cutting up his family and eating them for Christmas Dinner. It's later revealed in "Psycho Pete Returns" that he actually didn't; he was institutionalized to cope with his social anxiety and depression, and the rumors about him were mostly spread by the Gang.


  • Ax-Crazy: Subverted; it turns out that he was institutionalized for anxiety and suicidal tendencies, and was "more of a danger to himself than others."
  • The Dreaded: Mentioning his name is enought to instill a sense of fear into the listeners. He finally appears in season 10 and turns out to be a Gentle Giant undeserving of his terrible reputation.
  • Gentle Giant: When he finally appears in season 10 he turns out to be a large, timid man.
  • He Who Must Not Be Seen: Until "Psycho Pete Returns" in Season 10, he's only ever mentioned in rumors and horror stories.
  • I'm a Humanitarian: He murdered and ate his family. Except he didn't - this was just a rumor blown out of a proportion.
  • Insanity Defense: He got it. He's a psycho, you know. Except he's not.
  • "Just Joking" Justification: The Gang naturally assumes this after Ingrid tells them he threatened to blow up the school, but she tells them that he is legitimately Ax-Crazy.
  • Karma Houdini: He got the Insanity Defense, and he was able to threaten to blow up the school, forcing Ingrid to hire extra security. In "Psycho Pete Returns," he gets set free after his institute shuts down. It's later revealed that he never actually ate his family, it's just one of the many rumors that were started in response to the bad reputation the Gang got him.
  • Knight of Cerebus: Subverted. After all the build up of him as a monster, it turns out he's a soft-spoken Gentle Giant, who hung out with the Gang because they were accepting of him.
  • Nice Guy: In reality, he's a rather even-tempered man who's struggled with mental health problems, as opposed to the crazed killer the Gang made up.
  • "Not Making This Up" Disclaimer: Ingrid tells them that he is literally Ax-Crazy, and that he literally ate his entire family for Christmas Dinner
  • The Reveal: He never killed or ate anyone, the worst he ever did was yelling at some babies and making stray cats and dogs fight, which he did for the Gang's attention.

The McPoyle Clan

    In General 
  • Big Ol' Unibrow: All the family members have one.
  • Brother–Sister Incest: And brother-brother incest.
  • Commuting on a Bus: While heavily featured in the earlier seasons, the characters were phased out due to the actors playing the twins landing work on other shows. Currently, they appear once every couple of seasons.
  • Creepy Family
  • Evil Counterpart: They more or less take all of the Gang's worst traits as a group and crank them Up to Eleven.
  • Even Evil Has Loved Ones: They're a very close family, sometimes a little too close.
  • Eviler Than Thou: The Gang can't even hope to compete with them in terms of outright depravity.
  • Massive Numbered Siblings: In "The Gang Gets Invincible", many many siblings are shown together.
  • Trademark Favourite Food: Milk. They always drink lukewarm milk...they drink it instead of beer, have it instead of punch at a wedding and use it on their wounds.
  • The Rival: Probably the only characters who actually match (or rather, surpass) the Gang in depravity, as well as some of the only antagonists who consistently engage in mutual rather than one-sided competition with them.
  • Villainous Incest: It is actually a family tradition to sleep with and marry off other family members to prevent others from tainting their gene pool. Liam, however, convinces Ryan that after years of incest, it won't be them getting their gene pool tainted by others, but them tainting the gene pool of other families.

    Pappy 

Pappy McPoyle

    Liam & Ryan 

Liam & Ryan McPoyle

Played By: Jimmi Simpson & Nate Mooney

Creepy former elementary-school classmates of Mac and Charlie.


  • Big "NO!": Liam, the hammier of the twins, who often exclaims a massive no in conjunction with Suddenly SHOUTING!.
  • Bi the Way: They're screwing Margaret and each other.
  • The Corrupter: The McPoyle believe it's wrong to dilute family blood. Liam chooses to believe he's polluting the blood of outsiders.
  • Creepy Twins: Who sleep with each other.
  • The Ditz: Ryan. When Liam commands him to stab someone, he stabs Liam.
  • Eye Scream: Liam loses an eye during "The Maureen Ponderosa Wedding Massacre." He now uses a flesh-colored patch that is very off-putting. When the Gang tells him how disturbing it looks, he draws a cartoon eye on it.
  • False Rape Accusation: When they are first introduced, they are accusing their old gym coach of molestation because they hated his guts. Charlie rats them out.
  • Jerkass: They're both creepy and more than a little stand-offish.
  • The Leader: Liam generally appears to be the leader of the trio he forms with Ryan and Margaret.
  • Red Oni, Blue Oni: Liam is a Large Ham while Ryan tends to only speak when he needs to.
  • Suddenly SHOUTING!: Liam has a tendency to do this.
  • Those Two Bad Guys: Being brothers with a creepily close relationship, they're always seen together.
  • Twincest: A pair of fraternal male twins who are sexually involved.
  • White Sheep: Downplayed significantly, but Liam is consistently shown to be slightly more normal than the rest of his family, if only barely.
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    Margaret 

Margaret McPoyle

Played By: Thesy Surface

    Doyle 

Doyle McPoyle

Played By: Bob Rusch

  • I Coulda Been a Contender!: He had a pretty promising future in football, but it's brought to a halt by the Gang.
  • Uncanny Family Resemblance: Downplayed and lampshaded. He doesn't look exactly like his relatives. However once he says his name is "Doyle McPoyle", Mac and Dennis start to notice some similarities.

Other Characters

    Artemis 

Artemis Dubois

https://static.tvtropes.org/pmwiki/pub/images/artemis3.png
"These guys are playing hard to get. Gonna take off my bra, blast my nips."
Played By: Artemis Pebdani

Dee's friend from her acting classes who acts out a scene from Coyote Ugly. Artemis is overly serious about her craft and displays bizarre habits and outbursts. She is very open about her sexuality and often offers to perform in the nude, even when it is unnecessary. Recently, she was involved in a sexual relationship with Frank and the two shared a food fetish. She likes having sex with bacon bits in her hair because it "makes her feel like a cobb salad." She and Frank once had makeup sex in a dumpster behind Wendy's, where she incorporated a bun. She has openly proclaimed that she has a "bleached asshole".


  • The Alcoholic: She can't remember how she spends "most evenings."
  • Bi the Way: According to the season 5 extra features, she's had multiple lesbian encounters.
  • Bitch in Sheep's Clothing: She is extraverted, friendly and personable, but also extremely selfish and scheming.
  • Cloud Cuckoolander: Artemis is more bizarre than genuinely evil.
  • Commuting on a Bus: A recurring character in early seasons, her appearances have grown increasingly more sporadic over time.
  • The Danza: She shares a first name with the actress portraying her.
  • Fetish: Like Frank, she has a food fetish.
  • The Hedonist: Artemis likes to have fun, whether it means banging in public or getting insanely high at a Halloween party.
  • Informed Judaism: "Being Frank" reveals that she's Jewish, which is not mentioned in any other episode.
  • Large Ham: When she starts confessing her poor financial state, Dee can't tell if she's still doing some sort of performance.
  • Really Gets Around: She introduces herself to men by telling them she has a bleached asshole, arguing that they're "going to find out anyway."
  • Sixth Ranger: She's basically the only recurring character to have any sort of positive relationship with the Gang, and occasionally joins in on their schemes in some capacity.
  • Snake Oil Salesman: Sold New Age merchandise to gullible women in "The Gang Beats Boggs: Ladies Edition."
  • The Stoner: She frequently smokes marijuana, and has tried unsuccessfully to smoke it with Dee.

    The Lawyer 

The Lawyer

Played By: Brian Unger

An attorney who has had several run-ins with the Gang. Like the Waitress, his real name is unknown.


  • The Ace: Much more capable than the Gang and outwits them with ease during each conflict. Until season 11, where he not only loses the McPoyle vs Ponderosa case but also gets his eye pecked out.
  • Amoral Attorney: Averted. He starts out as a decent person until he's had enough of the Gang duct-taping his secretary and constantly bothering him. In fact, he seems weirded out by Dennis suggesting that he could "make love" to his soon-to-be-ex-wife while she sleeps as an act of good faith.
  • Ascended Extra: Originally, he was just the lawyer assigned to read Dennis and Dee's mother's will. Since then, he has frequently been at odds with the Gang in unrelated legal situations.
  • Break the Haughty: Throughout most of the series, he manages to remain two steps ahead of the gang in whatever zany scheme they have (intentionally or not) involved him in. This winning streak is broken when he loses the McPoyle vs Ponderosa case to them. He doesn't take it well.
  • Crazy-Prepared: Makes 50 copies of the contract he gives the Gang knowing they'd destroy them. Also keeps a gun in his desk in case someone busts in wanting to kill him.
  • Deadpan Snarker: He always has a witty put-down.
    Lawyer: It is just so nice to see you again, Mr. Reynolds, I see that you're still...just horrible.

    Lawyer: You know, I don't think I'm going to do anything close to that and I can clearly see you know nothing about the law. Seems like you have a tenuous grasp on the English language in general.
  • Everyone Calls Him "Barkeep": Like the Waitress, no one ever calls him by name and is only known by his job title.
  • Eye Scream: His right eye is pecked out by Royal McPoyle.
  • Guile Hero: A rare Hero Antagonist version.
  • Hero Antagonist: Amoral Attorney aspects aside, he does work within the law and try to genuinely protect his clients from the Gang's insanity, and does so without being pulled down to the Gang's level like most of their enemies. Probably the closest thing to a hero the show's got.
  • It Amused Me: The only reason the Lawyer got involved in Dennis' divorce was to spitefully give him a hard time.
  • Jerkass: He says some very nasty put downs pretty much every time he appears. Completely justified though, since we only ever see him when he's dealing with the Gang, who he immediately recognizes as a group of depraved morons.
  • Manipulative Bastard: He got the Gang to unknowingly sign a contract that also acts as a restraining order and gives him all the profits from their merchandise and makes about 50 copies, knowing that Mac will just eat the original.
  • No Name Given: He's yet to be given a name.
  • Omnidisciplinary Lawyer: The Gang and their adversaries use his legal advice no matter what situation.
  • Only Sane Man: The only recurring character who is intelligent, rational and successful in life.
  • Sitcom Archnemesis: One of his few character flaws is a tendency to antagonize the Gang when he could just leave well enough alone, making their rivalry with him one of the few that's actually mutual.
  • You Have to Have Jews: Averted, but for his own racist reasons Frank believes him to be Jewish by virtue of being a lawyer.

    Jackie Denardo 

Jackie Denardo

Played By: Jessica Collins

A local Philadelphia weatherperson with whom Dennis is deeply infatuated.


  • Buxom Is Better: She is extremely gifted in the chest area, which causes Dennis to fall in love with her. When she goes into a coma during Dennis' fantasy in "The Gang Saves the Day", Dennis euthanizes her when he learns that her breasts didn't survive the car accident she was in.
  • Hospital Hottie: She shows quite a bit of cleavage when she's featured as a nurse in "The Gang Saves the Day".
  • Leitmotif: Both times Dennis encounters her in person, she does a slow-motion walk to the tune of "Alone" by Heart.
  • Lust Object: Seemingly Dennis' ideal woman. He can't even talk straight when around her.
  • Ms. Fanservice: Despite being seen in a professional setting during both of her appearances, she shows off her large breasts pretty liberally.

    Ben Smith 

Ben Smith

Played By: Travis Schuldt

Dee's online chat buddy "soldier of fortune". He served as an American soldier in Iraq.


  • Brainless Beauty: Quite handsome, and is also dumber than a brick.
  • The Ditz: He's shown to be somewhat of a lovable idiot.
  • Extreme Doormat: He was so nice and innocent that Dee would tell him to sit and wait for her in the car, in blistering 100 degree weather, for hours on end, with the windows rolled up simply because she didn't mention to roll down the windows. Though he does eventually leave her when it's made clear that she's "a mean person."
  • Kindhearted Simpleton: Dimwitted but also one of the most genuinely nicest people in the show.
  • Nice Guy: Ben is just a sweet guy who's very considerate and pleasant to be around. He was very nice to Dee until he realized she was a jerk. At one point, he offered to help her when she had some trouble walking after falling down.
  • Too Dumb to Fool: He's yet to ever have his life wrecked by the Gang, in large part because he can't follow along with their confidence tricks, so he'll politely decline, walk away, and stay out of the scheme.

    Carmen 

Carmen

Played By: Brittany Daniel

A trans woman who was dating Mac. She is attractive but displays an obvious bulge in her pants. She keeps Mac interested in her with promises of undergoing sexual reassignment surgery and with constant flattery of Mac's physique.


  • Earn Your Happy Ending: Has yet to have her life ruined by the Gang... so far. In fact Dee actually helped Carmen achieve her dream of having a child by being her surrogate.
  • Easy Sex Change: Possibly averted she most likely kept saying she would lose her penis 'soon' due to how expensive it is. She also disappeared between the end of season 3 and the season 6 premiere, so the time frame isn't quite as compressed as it usually is in TV.
  • Even the Girls Want Her: Dee comments on her impressive implants in her first appearance.
  • Happily Married: Eventually, to Nick, following the completion of her surgery.
  • Morality Pet: For a time, she served as one to Mac. The montage we get to see of them spending time together while they were dating is genuinely sweet, and there's a small glimmer of hope that he'll rise above his usual awfulness to be with her. Unfortunately, this is not that kind of show.
  • Nice Girl: Carmen is very sweet and kind.

    Brian McIntyre 

Brian McIntyre

Played By: Dave Foley

The high school principal who hires Dee as a substitute teacher and Charlie as a janitor.


  • Butt-Monkey: The few times the Gang shows up to his school, there's always trouble. Especially the second time.
  • Extreme Doormat: A ridiculous pushover who is incapable of asserting himself in the face of Dee and Charlie, the Gang's preeminent punching bags..

    Rex 

Rex

Played By: T.J. Hoban

A local male model. Introduced as one of many attractive people vying for the position of the Paddy's Pub billboard model, he has been repeatedly rehired by the Gang whenever their schemes require some sex appeal.


  • Brainless Beauty: He's a male model. But he did things like eat a whole bowl of cockroaches before Frank told him to, just so he can be on a billboard (not so he could get paid, he just wanted to be on a billboard).
  • Cloudcuckoolander: Eating a bowl of cockroaches simply because you think it would impress someone is Charlie-level logic.
  • Determinator: He wanted to win the billboard competition very badly, to the point of eating an entire bowl of cockroaches unprompted just to impress the judge.
  • Double Standard: Abuse, Female on Male: "Dee Gives Birth" reveals that Dee is able to semi-regularly convince him to sleep with her by browbeating him into submission. While it's clearly framed in a way that makes Dee a terrible person for doing so, it's also Played for Laughs.
  • Fanservice Extra: Rarely does anything significant to the plot when he appears, and mostly just stands around looking handsome.
  • Formerly Fit: By seasons 13, he has gained a large beer gut as a result of falling for the Invigaron pyramid scheme. Ironically, season 13 also prominently features Mac acquiring the same chiseled physique that Rex was previously known for having.
  • Hunk: Rex is very muscular. The Gang describe him rather accurately as a beefcake.
  • Lust Object: Mac is heavily implied to have a thing for him pretty much every time he appears.
  • Mr. Fanservice: He's a model, and is regularly shown in various states of undress.
  • The Quiet One: Tends to have very few lines when he appears.
  • Shirtless Scene: Well, he is a model.

    Duncan & Z 

Duncan & Z

Played By: David Gueriera & Chad L. Coleman

Frank's bizarre friends that he met under a bridge.


  • Affably Evil: Z, who's quite friendly and cool. Not so much with Duncan.
  • Beard of Evil: Both of them have beards, and both are criminals who are seen beating the hell out of a couple who destroyed their wall (which is just a plastic sheet held up).
  • Black Best Friend: Z to Duncan.
  • But Not Too Black: Almost said word for word by Mac. When they try to win an award they invite Z to try and add some diversity but Mac says that he's too black and is just going to intimidate the judges.
  • Hyper-Awareness: Somehow, Z is able to determine that Dee is pregnant before she's really showing.
  • Nice Hat: Z is often seen wearing a nifty beanie hat.
  • Scary Black Man: Z, as played by the intimidatingly large Chad Coleman.
  • Those Two Bad Guys: They tend to appear together, and are very unsavoury criminals.
  • Toxic Friend Influence: Dennis considers them this for Frank, although Frank doesn't really need anyone's influence to be awful.

    Ernie 

Ernie

Played By: David Zdunich

  • Recurring Extra: He's a barfly who shows up in the background multiple times.

     Da Maniac 

Da Maniac

Played By: Roddy Piper

A washed-up, unstable Professional Wrestler. The Gang hires him to wrestle for the troops. He is later involved in the Gang's timeshare scheme.


  • Ax-Crazy: He smashes a lamp in his second appearance for no other reason than "Sometimes loud noises make the squirrels go in my head".
  • Cloudcuckoolander
  • Crazy Homeless Person: He appears to live out of his car and is clearly mentally ill.
  • Expy: He's one for Randy "The Ram" Robinson from The Wrestler.
  • Garbage Wrestler: When the Gang suggests that he use some "traditional" wrestling, he opines that nobody wants that "old school bullshit" anymore.
  • Hidden Depths: He shows some surprising skill as a salesman in his second appearance.
  • Noodle Incident: Claims to have had kids, but "not anymore".
  • Racist Grandpa: Calls Mac the N-word after apparently mistaking him for being black.
  • We Hardly Knew Ye: Maniac only made two appearances before the untimely death of Roddy Piper
  • Wrestling Doesn't Pay: He makes very little money wrestling and only charges the Gang fifty bucks for his services.

     Old Black Man 
Played By: Wil Garret

An old black man who Mac, Dennis, and Dee have been sharing a bed with ever since losing a bet with Frank.


  • All Just a Dream: The entirety of the episode "The Gang Turns Black" was simply a dream Old Black Man was having.
  • Ascended Extra: Has made several appearances in Season 12, after being little more than an ending gag in Season 11.
  • Everyone Calls Him "Barkeep": He's simply called "old man" or "old black man", though the Gang try not to call him the latter to avoid coming across as racist. Apparently his real name is Carl.

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