The 99 Greatest TV Characters Since Tony Soprano: #59-50

On January 10, 1999, a bathrobe-clad Tony Soprano first bent over to pick up a Star-Ledger in his driveway — and TV changed forever. We’re celebrating this new Golden Age of Television by paying tribute to our favorite TV characters who’ve debuted since The Sopranos premiered. No reality TV here, folks: just the 99 richest, most fascinating fictional characters from both comedies and dramas to grace the small screen over the past decade and a half. We love TV… and these people are the reason why.

59. Chuck Bass, Gossip Girl

The devil indeed wore Prada. And probably every other luxury label favored by billionaires-in-training, as he slept and schemed his way around the tabloid pages, the Upper East Side, Yale, and, as seasons went on, the world. But this smug one-percenter had to do far more than rock a signature scarf to become a suave villain you hated to love. Thanks to his perfectly cocked brow, silky voice, endless ambition, periodic flashes of vulnerability, and impeccable timing when delivering the show’s best zingers (“For people like us, a college degree is just an accessory, like a Malawi baby or a poodle”), fans found a way to forgive him repeatedly and rooted for his happy ending with soulmate Blair Waldorf. — Carrie Bell

Related: Vote For the Best TV Characters of the 2000s

58. Bree Van de Kamp, Desperate Housewives

Not-so-real housewives came and went, but Bree was the Stepford-style standout on Marc Cherry’s soapy primetime drama. Part perfectionist, part neurotic, Wisteria Lane’s queen bee experienced widowhood, alcoholism, business woes, a nervous breakdown, a couple of bad marriages, and divorce — all of which she handled with a determined self-possession that masked the vulnerable woman underneath. Plastic smile and home-baked bran muffins aside, this catering queen’s transformation from a prudish Martha Stewart clone to a dominatrix to a Kentucky state legislator helped define her as one of TV’s most fascinating housewives. — Victoria Leigh Miller

57. King Joffrey Baratheon, Game of Thrones

Never has someone so hateable also been so strangely lovable. Westeros’ not-so-dearly-departed boy king had a short, stormy reign marked by bad choices, bad strategy, and a really bad attitude. But his awfulness gave the other characters — many of whom aren’t exactly shining examples of virtue either — a common foe to scheme against, and it also made his eventual comeuppance all the more awesome. (It helps that actor Jack Gleeson is such a doll off-screen; feel your hatred melt as you watch him play with this puppy.) Admit it… hasn’t King’s Landing seemed like a less interesting place without King Joffrey to kick around? — Ethan Alter  

56. Josh Lyman, The West Wing

What a mensch! On a show with Martin Sheen playing the President of the United States and Rob Lowe dazzling White House staffers with his beauty, it could have been easy for the lesser-known Bradley Whitford’s Deputy Chief of Staff to fall into the background. But that didn’t happen. Josh’s witty, moving speeches, boyish charm, and passion for policy shined through and moved us weekly for seven seasons. In fact, he became so deeply likable that on more than one occasion, my mother told me I needed to marry him (never mind that part where he’s a fictional TV character) — and she’s not an easy one to please. — Breanne L. Heldman

55. Charlie Kelly, It’s Always Sunny in Philadelphia

Even among the selfish misfits of Paddy’s Pub, Charlie’s particular brand of crazy stands out. He’s illiterate, unhygienic, prone to fits of rage (“I will smash your face into a jelly!”), and addicted to huffing paint… but underneath all that, he possesses the tender soul of an artist. (Although when he does write songs, they tend to be about unwanted sexual advances from men at night.) Despite his inventive mind — Kitten Mittens! — and his tireless dedication to “Charlie Work,” he still hasn’t won the heart of The Waitress after stalking her for ten seasons now. C’mon, give the poor guy a chance! Actually, you probably shouldn’t. — Dave Nemetz

54. Patty Hewes, Damages

How do you build a TV series around a cold, ruthless, immoral lawyer as your main character? Have her be as brilliant, sarcastic, and ultimately as tragic as Patty Hewes. Hewes comes on all haughty, a high-powered Manhattanite accustomed to being obeyed, but she’s truly as low-down as a snake. She coerces witnesses to lie, has inspired at least a couple of suicides, and made a virtual slave of her mentee Ellen Parsons… before Ellen learned to be as chilly and relentless as her mentor. Alienated from her family, Hewes is ultimately a tragic figure, walled off from ordinary emotions, but her brilliance as a thinker and a plotter is undeniably admirable. — Ken Tucker 

53. Ari Gold, Entourage

Even when Entourage began to flail, short-fused Hollywood super agent Ari Gold stood LOUD! ANGRY! YELLING! and altogether unforgettable. All that pushy arrogance got things done: No one could wheel and deal and still give the middle finger quite like Ari. But still, somewhere deep in the depths of his soul (yes, he had one), there was never any doubt that Ari loved his wife… and Vince… and even Lloyd, the assistant he terrorized on a weekly basis. Oh, who are we kidding? The guy was a giant puddle of gooey mush. — BLH

52. Denny Crane, Boston Legal

Few characters can sum up their essence in two words, but William Shatner’s besuited, badass delivery of “Denny Crane” says it all. First introduced on The Practice — before he and fellow attorney Alan Shore made their scotch-and-stogie balcony chats a Boston Legal staple — Denny is unapologetically randy, irreverent, and ridiculous. But with an enormous, foolish heart and a childlike wonder in his eyes, he’s also impossible not to like. Just ask Alan, who married an Alzheimer’s-stricken Denny in the series finale. There were practical reasons, for sure. But there was also this: “I’ve always wanted to remarry before I die,” Denny said. “And like it or not, you’re the man I love.” — Mandi Bierly

51. Sydney Bristow, Alias

A secret agent with an extensive wardrobe to accompany her sizable list of combat and espionage skills, Sydney remained a compelling heroine even as Alias itself began a rapid downhill slide after Season 2. For that, credit J.J. Abrams with creating a proactive heroine who never allowed herself to be a victim of circumstance, and Jennifer Garner with unerringly finding the emotional reality amidst the craziest of storylines. The antidote to the typical stoic, stone-faced spy, Sydney was a whirling dervish of hands, feet, and heart. — EA

50. Seth Cohen, The O.C.

If the world seems safer for geeks on television today, we have Orange County’s resident comic book fanboy to thank. Seth never hid his Comic-Con-ready proclivities from his family and friends, peppering his speech with nerd-isms and merrily slaving away on his own comic (Atomic County), trusting that everybody would eventually understand his version of cool. And he was right. Want proof? He got the hottest, snobbiest girl in school to cosplay as Wonder Woman. Talk about revenge of the nerds. — EA

Previously:
The 99 Greatest TV Characters Since Tony Soprano: #99-90
The 99 Greatest TV Characters Since Tony Soprano: #89-80
The 99 Greatest TV Characters Since Tony Soprano: #79-70
The 99 Greatest TV Characters Since Tony Soprano: #69-60