While Helluva Boss is well-liked due to its quirky cast of characters, a lot of that quirkiness has made them rather divisive in recent years.
- The main character himself, Blitzo. Some fans think to be a hilarious character and are intrigued by his Hidden Depths while others hate him for being an annoying and obnoxious Jerkass.
- Moxxie began getting this reaction as the series continued, particularly during Season 2. Many adore him for being the most moral of the group, having a genuinely charming sweetness to him that makes him adorkable, and having a very tragic past and need for approval that makes him immensely sympathetic. Others however loathe him for his attempts at being moral coming across as self-righteous and ill fitting for the line of work he's in, his overshadowing Millie in terms of relevance, and his need for approval causing him to have an insufferable and self-centered ego at times.
- While Millie is well-liked for being a Badass Adorable Action Girl with a cute relationship with Moxxie, some people dislike her for being an underdeveloped Satellite Love Interest for Moxxie.
- Loona started off as a fan-favorite (especially with furries) but as the series progressed, she went from an Ensemble Dark Horse to a very divisive character. Some like her for her snarky personality and think that she provides some of the funniest moments in the show while others hate her for being your typical "misunderstood teenage goth girl" who is bratty, temperamental and mistreats others around her as little more than nuisances, even her adoptive father, Blitzo.
- Stolas. Many like him for his for being a good father to Octavia, proving that despite being a Depraved Bisexual/Depraved Homosexual he still has a heart, and the sympathetic reasons behind his infidelity. Others have increasingly criticized how he's continued such even after realizing the harm it caused, relies on demonizing his wife Stella to keep his infidelity sympathetic, and taking focus away from other characters. His relationship with Blitzo is seen as either cute and funny, entertainingly flawed, or straight toxic due to their power imbalance making it hard for Blitzo to feel safe saying no, Blitzo's visible discomfort around him in the first few episodes, the transactional nature of it, and the Retcons to make it come off as genuine romance. His relationship with Octavia is also divisive; while no fan can reasonably deny he loves her, whether he's actually a Good Parent is debated.
- Stella, especially after 'The Circus'. While her screen-time was severely limited in Season One, only having around half a minute of screentime in the entire season, many fans speculated on the kind of person she was, and how Stolas' affair has affected her (aside from her now wanting him dead for it). Plus, she wasn't hard on the eyes to some. To say some people were displeased with her being a cruel, sadistic woman who wanted to torment Stolas would be an understatement. Many would defend that Stella was always meant to be an awful person, others did not like this direction for various reasons, from some accusing the writers of writing her this way to make the already divisive Stolas more sympathetic in spite of his adultery, to her motivation just being dull and narmy. The implications in 'Western Energy' that she's not so bright have only caused further division. There's a third group who don't mind her being completely evil but just wish she had more personality than just sheer sadism. This group often brings up Valentino from Hazbin as an example of how its possible to write a vile abuser with more personality traits than just abuser.
- Verosika Mayday. She was well-liked for her attractive design, being voiced by Cristina Vee, and for her adversial history with Blitzo, being one of many people he had wronged in her past. A lot of people don't like how Verosika is labeled by some as an evil character and is treated by some as being just as bad as malicious and sadistic characters like Stella and Crimson. However, some find her to be too spiteful and petty, having trouble feeling sorry for how Blitzo treated her. People especially did not like how she and her entourage assaulted Moxxie just because of her disdain for Blitzo.
- The C.H.E.R.U.Bs. Some like them for how adorably sweet they are and felt bad for them when they got kicked out of Heaven while others hate them for being too overly saccharine and sweet and found their dedication to helping others to be more annoying than cute.
- Crimson. While liked by many for being a intimidating and deplorable mob boss who abused his son and had his wife killed, others were not so enthused with him. Some felt his intimidation and evil factor is undercut by his questionable choices, such as not questioning if Chaz was actually rich and being fooled by Fizzarolli's distraction song, and the fact that in both his outings, his goons and himself are easily defeated by Millie in "Exes and Oohs" and Blitzo and Fizzarolli in "Oops" (and Crimson even had Striker in his employ). Others found him to be a retread of the 'bad father, dead/absent mother' backstory, which was already done by Stolas and Blitzo at this point, as well as a generic mob boss archetype that does nothing new or interesting with the archetype either.
- Queen Bee-zlebub. Some liked her for being a very unique and interesting take on the Sin of Gluttony (especially with furries), and especially enjoyed the nod to Jayjay from Vivziepop's Die Young video, down to getting Kesha, the original singer of the song. However, others were not impressed, as some found Queen Bee's design and personality to be so far removed from the original sin that some didn't even catch on that she was THE Beezlebub until they saw her name in the credits. Vivziepop's Dear Negative Reader reaction did little to quell things.
- For some, Chaz is among the funniest characters in the show, with many adoring Eric Schwartz's voice work for him and wishing that his Hidden Depths and his past relationships with Moxxie and Millie got explored more. Others found him to be one of the most insufferable characters on the show for only being a walking sex/dick joke and felt that he completely dragged down the sole episode he appeared in. A third camp still finds him annoying or were ambivalent but felt that he shouldn't have been killed off after only one episode as he could have been fleshed out more.
