Crazy Is Cool: Scarlet, even more so once her sisters start helping. For starters, she once made a lawn mower design that incorporated A BLACK HOLE and, more recently, cracked perpetual motion with a Slanky.
Fridge Logic: Art is often unable to convince the authorities to help him with various situations, with the idea being that the situations are too weird for anyone to believe. Regular enough for humor value, but one of the weird things that no one believes (or he thinks no one will believe) is that his housemates are anthropomorphic animals. Yet no one bats an eye when Pip, Kat, or Scarlet go out in public. Kat and Hilary both apparently attended a public school, Kat has a job with a human boss and Hilary is a client for Art's company at one point and the head of a lingerie company. There are at least two other anthropomorphic animal background characters (the cat-boy Kat meets at the club, and the cat-man Hilary seduces). So if anthropomorphic animals are so accepted, why would the police not, say, believe a call that a squirrel girl broke into the house?
Harsher in Hindsight: This strip, at the time a throwaway gag about Pip being a perv, loses a lot of its humor after he was played for a fool and subsequently dumped by Hilary, especially after the reveal that Pip was truly happy not to be alone anymore, whereas Hilary felt nothing for him.
Heartwarming Moments: When Kat is feeling insecure because her rival Hilary looks good as a pin up, Art points that she doesn’t have the personality to back up her looks, unlike Kat. D’awww.
It turns out Hilary was luring Pip along with the promise of sex, only to knock him out with drugs and have sex with another man instead, and claim that the two of them had a great time the next morning. Made worse when Pip mumbles in his sleep that he think she's gorgeous and is just happy to have someone who wants to spend time with him.
To make matters worse, the entire arc began as if trying to convince us Hilary was redeemable and that Pip was her salvation. Not only does she blow this by having an affairafter drugging Pip, she also reveals this was all a ploy to seduce her way up the chain of command to get out of her employment rut. And only for the sake of twisting the knife further, she leaves it up to Kat to reveal to Pip he had been used all this time. Post-arc, fans can agree Hilary has absolutely no redeeming qualities now.
Tear Jerker: The entire debacle with Pip and Hilary. After thinking that Hilary actually cares about him, Pip finds out that she's been using him to leave her unemployment rut, leaving him heartbroken. Even after everything goes back to normal and even after all that, Pip still can't shake off his pining for Hilary.
Poor Leonard. What he has to go through isn't all that dramatic or horrible, really, but that changes nothing.
It's kind of upsetting that most of his daily grievances involve being denied food, either because Scarlet steals it or because everyone else is too lazy to just open a can for him.
Doesn't help that Kat tends to designate caring for him to Scarlet, the Cloudcuckoolander.
Art. Especially back when the squirrels turned him fat, making his life worse in practically every way, and everyone acted like it was his fault.
A big part of what makes Art the woobie is his normalcy. His housemates include a photographer cat-girl, a comic book geek penguin with loose morals, four deranged squirrel geniuses, and a legion of miniature shadow people. The only thing separating him from the reader is the 4th wall. If any of the readers found themselves in the same situations, they might ball up and cry. Granted, while things routinely hit the pits for Art, his friends are there for him, in a true nakama fashion.
Jerkass Woobie: Pip goes from Unsympathetic Comedy Protagonist to distressingly sympathetic when we learn that Hilary has been using him to cover for her at the charity shop and then stringing him along with the promise of sex, only to drug him and go off to sleep with another man. Worse yet, Pip's drugged muttering reveals that he's genuinely happy to have finally found someone who just wants to spend time with him.
and use high-tech weaponry to cook popcorn,