For some reason, YouTube keeps sending me videos about anti-heroes. Maybe it’s the algorithm trying to tell me something.
Maybe it’s the scoundrel in my father, the rebel in my sister, or just the part of me that enjoys watching good people break rules.
Whatever the reason, I always find myself drawn to supporting characters—especially the ones who bend the law, stretch morality, or at least make the lead characters’ lives more interesting.
A great supporting character can make or break a show for me. I can forgive a dull protagonist if the side players bring enough depth, chaos, or dry humor to keep me engaged.
In some cases, I don’t even care about the main character—I’m just there for the guy skulking in the shadows or the woman quietly outsmarting everyone else in the room.
That’s what brings me to these four: Omar Little from The Wire, Peggy Olson from Mad Men, Richard Harrow from Boardwalk Empire, and Bart Curlish from Dirk Gently’s Holistic Detective Agency.
Omar Little, played by the late, great Michael K. Williams, is one of the best characters ever put on television, and I will die on that hill. A shotgun-wielding Robin Hood who robs drug dealers while whistling The Farmer in the Dell, Omar is as terrifying as he is principled. He has one rule: he never harms innocent people. He also has no problem strolling through Baltimore in a silk bathrobe, proving that confidence is 90% of survival. Omar doesn’t just add depth to The Wire—he steals every scene he’s in, often while literally stealing something else.
Then there’s Peggy Olson, played by Elisabeth Moss, who starts Mad Men as Don Draper’s wide-eyed secretary and ends it as a whiskey-drinking, cigarette-smoking, pants-wearing powerhouse. She’s ambitious, she’s sharp, and she slowly realizes she might be more talented than every man in the office combined. Watching Peggy’s rise through the misogynistic world of 1960s advertising is as satisfying Don Draper’s tortured monologues.
Plus, she walks into the office once with a cigarette in her mouth and an octopus porn poster under her arm, and if that’s not character development, I don’t know what is.
Richard Harrow, played by Jack Huston in Boardwalk Empire, might be the most tragic figure on this list. A World War I sniper with half his face blown off, he wears a tin mask to cover his injuries and speaks softly, as if trying not to take up too much space. He’s an assassin, but a polite one. He’ll shoot a dozen gangsters in one scene and then read a bedtime story to a child in the next. Richard never fully believes he belongs in the world of crime—or in the world at all—which makes his story all the more heartbreaking.
And finally there’s Bart Curlish, played by Fiona Dourif in Dirk Gently’s Holistic Detective Agency. If you haven’t seen the show, first of all, I’m sorry, because it was canceled far too soon.
Bart is a “holistic assassin,” which means she kills people at random, trusting the universe to guide her toward the right targets. She’s equal parts terrifying and hilarious, barreling through life with the certainty of someone who’s never questioned whether murder might not be the answer. Somehow, she’s also one of the most lovable characters in the show, mostly because she doesn’t care what anyone thinks—about her, about fate, about anything.
Now, before anyone asks why Jesse Pinkman isn’t on this list: Breaking Bad doesn’t count. Jesse and Walter are co-leads, not supporting characters. The same goes for The Sopranos. Every character in that show revolves around Tony, so no matter how great Paulie Walnuts or Christopher Moltisanti are, they don’t quite fit the bill. And The Simpsons? Too animated. Literally.
These characters aren’t just background players—they’re the reason these shows work as well as they do. They break the rules, they bend the story, and in some cases, they outshine the leads entirely.
Maybe that’s why I love them. Or maybe it’s just the YouTube algorithm leading me down another rabbit hole.
Either way, keep the algorithms coming.
