Across the past five decades, what was once a simple catchphrase has become an unassailable fact: “It’s not TV. It’s HBO.”
Home Box Office first began broadcasting as a pay-cable network 50 years ago today, and what used to be just a channel for old movies and boxing matches has grown into arguably the single greatest producer of quality programming in television history. HBO’s original programming ambitions started out small with raunchy comedies like 1st & Ten and Dream On, but the arrival of The Larry Sanders Show in 1992 announced it as a serious player in the TV content wars. Then with the debut of The Sopranos in 1999, HBO blasted off into an era of massive success, with a tidal wave of critical acclaim (it regularly tops all networks in Emmy wins each year) and a flurry of buzzy watercooler hits from Sex and the City to Game of Thrones.
HBO’s pay-cable status allows its original series to push the established boundaries around sex, violence and subject matter, resulting in an offbeat, thought-provoking and often groundbreaking lineup of shows. And those shows have introduced us to a host of unforgettable characters over the years: heroes and villains, superstars and sidekicks, kings and court jesters. To celebrate HBO’s 50th birthday, we’re naming the 50 greatest characters ever to appear on its original series and ranking them, based on how fascinating, complicated, and original they were. Now HBO’s exemplary output over the years did make this a truly daunting task, but we debated, we voted — and we’re happy with the results.
Read on to see how we ranked the 50 best characters HBO ever gave us — and of course, we want to hear from you, too: Hit the comments to tell us your favorite characters we left off and who you’d rank in your personal Top 5.
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Rhaenyra Targaryen, House of the Dragon
Image Credit: Courtesy of HBO (2) It just wrapped up its freshman season, but HBO’s Game of Thrones prequel has already managed to live up to the impossibly lofty expectations we had for it, thanks to intricately crafted characters like this steel-spined queen of Westeros. As played by Milly Alcock in Season 1’s first half, Rhaenyra was a precocious teen princess who embraced her destiny with a keen mind and a regal air. Then Emma D’Arcy took over as an adult Rhaenyra in the season’s latter half, flashing a fiery temper and a rugged determination to honor her father Viserys’ legacy. Dragon‘s epic tale is just getting started, and we can’t wait to bear witness to Rhaenyra’s next power move.
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Vernon Schillinger, Oz
Image Credit: Courtesy of HBO Oz was a vital chapter in HBO’s development: its first original drama series, and one that took full advantage of pay-cable’s freedoms to tell the harshly violent story of inmates locked up in a maximum-security prison. The show made some viewers wince with its graphic depictions of prison life, but it also offered a host of superb performances, led by future Oscar winner J.K. Simmons as smug white supremacist Vernon Schillinger. A sadistic racist who raped his fellow inmates to demonstrate his superiority and bullied much larger men through sheer force of will, Schillinger was a chilling portrayal of evil — but he also foreshadowed HBO’s willingness to look into the very darkest depths of humanity to find compelling drama.
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Armond, The White Lotus
Image Credit: Courtesy of HBO Emmy winner Murray Bartlett’s dutiful Maui resort manager was a character that we quickly empathized with — incessantly harassed as he was by douchey, overly demanding guest Shane — but who then betrayed our trust by swan-diving off the wagon and succumbing to a most unflattering, drugs-infused spiral. In the end, his behavior was quite s—tty.
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Judy Gemstone, The Righteous Gemstones
Image Credit: Courtesy of HBO If this list were ranked by delusional weirdos, Judy would claim the No. 1 spot, no contest. Played to deranged perfection by Edi Patterson, Judy might be the strangest one in a family full of Gemstone oddballs, constantly self-destructing in an effort to get her slice of the megachurch pie. And though Judy’s emotional immaturity remains one of her funniest characteristics — The Righteous Gemstones is, after all, largely about family dysfunction — her unexpected bond with Aunt Tiffany in Season 2 gave the character some overdue, and no less entertaining, growth.
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Barry Berkman, Barry
Image Credit: Courtesy of HBO At first, we admit we were kind of rooting for Barry: The killer for hire played by Bill Hader was almost a likable goof as he yearned for an acting career in this pitch-black comedy that blends sharp Hollywood satire with violent mob warfare. (Hader has also flashed some terrific deadpan humor along the way.) But in later seasons, the mask has come off, and Barry has become a terrifying menace with an explosive temper, taking the series to some very bleak places — and Hader to new acting heights. We can officially say we’re no longer rooting for Barry… but we also can’t take our eyes off of him.
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Murray Hewitt, Flight of the Conchords
Image Credit: Courtesy of HBO Murray? Present. Yes, this list wouldn’t be complete without the presence of Bret and Jemaine’s adorably incompetent band manager on this musical comedy quirkfest. Relentlessly upbeat and absolutely unqualified, Murray did his best to book the titular duo’s music gigs while working his day job at the New Zealand Consulate — and did neither job very well, to be honest. (Bret and Jemaine ended up playing a lot of half-empty coffeehouses.) But Murray was unfailingly loyal and a joy to watch, too, thanks to Rhys Darby’s beautifully blank performance that approached Michael Scott levels of obliviousness.
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Jared Dunn, Silicon Valley
Image Credit: Courtesy of HBO This Julia Roberts superfan and bird watcher extraordinaire served as Richard Hendricks’ awkward but highly intelligent righthand man. Although he was Pied Piper’s punching bag of sorts for all six seasons, his inability to understand most of Gilfoyle and Dinesh’s roasts only added to the team’s overall comedy of errors. Oh, and also, “this guy f–ks.”
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Nicki Grant, Big Love
Image Credit: Courtesy of HBO The second of polygamist Bill Henrickson’s three wives once described herself as “spiteful and jealous and mean.” While those are certainly not qualities one should be proud of, Chloë Sevigny’s standout performance and the show’s sharp writing made watching Nicki in all her caustic, sneaky glory a delight. Nicki was rash and unpredictable (she pushed her own father down a flight of stairs!), blunt to a fault and sometimes almost childlike in her defiance. But underneath all those rough edges were also moments of true vulnerability and deep love, making for a truly memorable, multifaceted character who earned a spot not only in Bill’s family, but also our hearts.
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Ja'mie King, Summer Heights High/Ja'mie: Private School Girl
Image Credit: Courtesy of HBO Aussie chameleon Chris Lilley has blessed the world with countless memorable characters across his various mockumentaries — including Summer Heights High and Angry Boys, both of which aired Stateside on HBO — but none have left an impression quite like (robbed!) Australian of the Year and Hillford Medal nominee Ja’mie King. Ruthlessly selfish, impossibly offensive and unquestionably quiche, she was an absolute nightmare to everyone who crossed her path. And she was damn good TV.
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Didi Ortley, Getting On
Image Credit: Courtesy of HBO Niecy Nash scored a pair of Emmy nominations (among other accolades) for her work as Denise “Didi” Ortley, a no-nonsense nurse with a heart as big as her mouth. A bright light in the hospital’s otherwise dreary geriatric wing, Didi was a true force of nature — even if her Khmer was a little rusty.
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Dolores, Westworld
Image Credit: Courtesy of HBO Sweet, unassuming rancher’s daughter? Fearsome and legendary Deathbringer? Temporary Charlotte Hale (for a hot minute)? No matter which version of Dolores (most often played by Evan Rachel Wood) is on screen at any given time, we can never tear our eyes away from her.
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Leon Black, Curb Your Enthusiasm
Image Credit: Courtesy of HBO The addition of Leon in Season 6 added yet another layer to Curb‘s carefully crafted comedy. Larry’s street-smart sidekick is always on the ready with some relevant bit of advice, despite his highly unconventional methodology. Leon was a unique add to the show’s fictional Hollyweird, and his rough-around-the-edges approach and crass sense of humor helped him fit right in.
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The Cryptkeeper, Tales From the Crypt
Image Credit: Courtesy of HBO Equal parts endearing and horrifying, this legendary bag of bones (voiced to perfection by John Kassir) always knew how to set the right tone for an evening of spine-tingling tales. With all respect to Ryan Seacrest, when we hear the phrase “host with the most,” we think of this skeletal icon. Plus, like all late ‘80s/early ‘90s pop culture staples, the Cryptkeeper occasionally dabbled in rap. Enjoy.
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Mare Sheehan, Mare of Easttown
Image Credit: Courtesy of HBO It was a role so juicy that it lured Kate Winslet to TV — and won her an Emmy. Winslet headlined the HBO murder mystery as a hard-edged police detective investigating a mysterious death in her close-knit Pennsylvania town. Mare was a tough nut to crack and not exactly likable, but we eventually learned that she had serious demons of her own to deal with, and Winslet’s powerhouse performance helped us sympathize with the prickly cop. It’s a shame Mare was just a limited series, because we’d definitely watch more of Mare Sheehan, given the chance.
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Kenny Powers, Eastbound & Down
Image Credit: Courtesy of HBO This former major leaguer-turned-middle school gym teacher brought a whole new class of cringe to HBO. Despite trying to reclaim his fame at every turn, Kenny’s arrogance and narcissism sabotaged his every effort. Luckily for us, watching him fumble his way through life was so hilarious and horrific that we just couldn’t look away.
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Hannah Horvath, Girls
Image Credit: Courtesy of HBO Lena Dunham’s indie comedy blazed its way to pop-culture ubiquity and then faded just as quickly, but it still left us with some indelible characters, led by Dunham’s aspiring writer Hannah. For a lead character, Hannah was at times, well, infuriating: spoiled, selfish and prone to terrible decisions. But her brave vulnerability — and Dunham’s as well — gave us a vivid look into the lives of funny yet flawed New York City hipster twentysomethings. As Hannah said herself, she may not have been the voice of her generation, but she was a voice of a generation… and we’re grateful we got to hear it.
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Miranda Hobbes, Sex and the City
Image Credit: Courtesy of HBO We’re snarky writers, so of course we consider ourselves Mirandas. The cynical attorney played by Cynthia Nixon brought an acidic zing to HBO’s hit sex-com, with her grounded pragmatism serving to balance out Charlotte’s starry-eyed romanticism. But Miranda wanted to find love, too, and Nixon’s tender scenes with David Eigenberg’s goofy bartender Steve brought an unexpected warmth to the supposed ice queen. She was also a badass career woman and a dedicated friend to Carrie — even when Carrie didn’t deserve it. If we had to pick one Sex and the City gal to be friends with, we’d be guzzling Cosmos and slinging insults at Miranda’s table.
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Noho Hank, Barry
Image Credit: Courtesy of HBO Easily the most cheerful mobster we’ve ever encountered, this Chechen sweetheart played so winningly by Anthony Carrigan has shot his way to number one in our hearts with a bullet. (A hail of bullets, really.) With his silly pop-culture musings and bromantic obsession with Barry, Hank helps lighten up what can be a very dark comedy, with Carrigan stealing scenes left and right. His zest for life is positively infectious, too. He may not really be that well suited to being a ruthless crime boss, but he is the perfect antidote to Barry‘s more grim tendencies.
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Madeline Mackenzie, Big Little Lies
Image Credit: Courtesy of HBO Madeline Martha Mackenzie seemed like an easy nut to crack when we first met her: Armed with endless quips and deeply held convictions, Madeline initially came off as little more than a judgmental Monterey mom. But throughout HBO’s adaptation of Liane Moriarty’s novel, Madeline revealed magnificent depth as she confronted her own infidelity and insecurity, grappling daily with how to raise her children while being deeply flawed herself. In an ensemble full of richly realized female characters, Madeline was perhaps the most fascinating — a funny, fiercely loyal friend who was at her most compelling when she was at her most imperfect.
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Livia Soprano, The Sopranos
Image Credit: Courtesy of HBO Oh, you wanted someone else to make this list instead? Poor you. Tony’s domineering mother only appeared in two-plus seasons of the HBO mob drama, but her relentlessly belittling parenting style — and Nancy Marchand’s exquisitely bitter portrayal — made her an all-time great mother from hell. She criticized just about every thing Tony did, to the point where she conspired with Uncle Junior to take her own son out, and made everyone else in her life miserable with her caustic complaints about, well, everything. It’s truly a shame Marchand died midway through Season 3, both because her performance was so tremendous and because we never got to see how much more psychological damage Livia would’ve been able to inflict.
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Ari Gold, Entourage
Image Credit: Courtesy of HBO So yeah, this bromantic comedy about four dudes climbing the showbiz ladder isn’t exactly the most fondly remembered series in HBO’s storied history — and it didn’t age all that well, either. But Entourage did give us an unforgettable portrait of Hollywood hubris in rage-prone agent Ari Gold, a role so savage that it won Jeremy Piven three straight Emmys. Ari was a hotheaded force of nature, abusing his staff and aggressively promoting his clients to get them the best possible deal by any means necessary. In other words, these days, he’d be cancelled in the blink of an eye. But in those heady George W. Bush-era days, he ruled the roost, and watching him wheel and deal was Tinseltown entertainment at its finest.
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Susie Greene, Curb Your Enthusiasm
Image Credit: Courtesy of HBO While Larry David certainly gets into it with literally everyone on this show, nothing gives us more joy than seeing a simple chat with Susie escalate into a full-on screaming match. Susie’s unbridled rage and contempt for Larry are both ludicrous and laughable. Even when these two seem to be on the same page, we’re always gleefully waiting for the inevitable explosion (and Susie’s tirade of F-bombs) to follow.
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Shiv Roy, Succession
Image Credit: Courtesy of HBO The youngest Roy sibling is a fascinating if at times maddening blend of those immediately above her, mimicking as she does Kendall’s capacity to be cutthroat, yet susceptible to Roman’s immature inclinations. Sarah Snook gives us a savvy, sassy someone to root for amidst the series’ toxic boys club, even if we know that — all too often, sigh — Logan will leave his daughter’s ambitious dreams unfulfilled.
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Lafayette Reynolds, True Blood
Image Credit: Courtesy of HBO As a gay Black man living in the backswamp town of Bon Temps, La., this fabulous short order cook refused to take crap from anyone, human or otherwise. (His legendary takedown of a homophobic diner in the show’s first episode is a favorite among fans.) Nelsan Ellis’ character lit up every room he entered, whether he was there to crack a joke or conjure a spirit. Because when you shine as brightly as Lafayette, everyone wants to be around you — even the dead.
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Jonah Ryan, Veep
Image Credit: Courtesy of HBO Jonah, aka “Supercalifragilisticexpialid–kcheese,” would have been the most reprehensible of all of Veep‘s politicians had Timothy Simons’ portrayal not made it so abundantly clear that this man-child was completely unaware of his repulsive behavior. He really didn’t know better, which almost made you feel bad whenever he was berated by his even more repugnant Uncle Jeff. He also gets points for being among the first politicians to attempt to abolish Daylight Saving Time. (A monster and a hero, this one.)
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Nate Fisher, Six Feet Under
Image Credit: Courtesy of HBO The Fisher family’s eldest son never wanted to follow in his father’s footsteps, but ultimately, that’s exactly what he did in more ways than one. Nate tried hard to find happiness and be a stand-up family man, despite his flaws and inability to reconcile his true feelings. Through the disappearance of his wife and his debilitating, series-spanning illness, Nate confronted his own mortality, and as a result, we were forced to follow suit.
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Maeve, Westworld
Image Credit: Courtesy of HBO Even before she became self-aware, we loved Maeve, a bold and ballsy host with a quick wit and a take-no-guff attitude. All of those attributes only became stronger as her knowledge of the world, both inside and outside the park, grew. And watching Thandiwe Newton’s character as she deduced the ins and outs of Delos’ dealings, often peppered with a sizzling one-liner, was the definition of the word “sublime.”
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Arya Stark, Game of Thrones
Image Credit: Courtesy of HBO Thrones author George R.R. Martin has said that Maisie Williams’ scrappy Stark kid was one of the few inherently good characters in HBO’s adaptation of his books. We concur. It was just so easy to cheer on Ned and Catelyn’s forthright younger daughter as she overcame immense — and prolonged! — tragedy, eventually turning herself into a warrior fit to take down the formidable Night King.
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Tanya McQuoid, The White Lotus
Image Credit: Courtesy of HBO Wee-hee! Mike White’s luxury vacation cringe comedy is packed with colorful characters, but the unquestioned VIP guest is the notorious Miss McQuoid, who gave Jennifer Coolidge the role of a lifetime — and an Emmy. Filthy rich and slightly dazed, Tanya is an ultra-pampered world traveler who drinks too much and falls in love too easily, and her loopy one-liners crack us up, just as her desperate desire to be loved breaks our hearts. Tanya was such a hit that White even brought her back for Season 2, and with a character as lovably unhinged as this, we’d happily watch her wander around the globe for another ten seasons.
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Issa Dee, Insecure
Image Credit: Courtesy of HBO Issa Rae’s bittersweet chronicle of Black life in L.A. was low-key one of the greatest comedies HBO has ever produced, and Rae not only co-created the series, she also starred as Issa Dee, whose struggle to find her voice in a hostile world was somehow both refreshingly unique and intensely relatable. Issa definitely had her goofy side — those hype-up sessions in the mirror! — and she made some highly questionable decisions along the way, in her professional and her romantic life. But every time she stumbled, she got back up, which made her eventual triumph and self-assurance all the sweeter.
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Hank Kingsley, The Larry Sanders Show
Image Credit: Courtesy of HBO Hey now! Garry Shandling’s peek behind the scenes of a fictional late night talk show was HBO’s first truly great series, and nowhere was its savagely satirical lens more finely honed than when it was focused on Hank, Larry’s oafish sidekick. Impossibly vain and deeply self-loathing, Hank’s nice-guy routine vanished as soon as the cameras stopped rolling, with him abusively berating his staff and then cravenly begging Larry for more screen time. Played magnificently by Jeffrey Tambor, he was the ultimate Hollywood phony, and yet we loved watching him flail, in an early test case that proved we don’t have to like a TV character to be fascinated by them.
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Amy Jellicoe, Enlightened
Image Credit: Courtesy of HBO Ever have a friend who goes away on a weekend wellness retreat and comes back thinking she has the whole world figured out? Yep, that was Amy, the lead character of Mike White’s intricately observed (and too short-lived) corporate comedy. After a meltdown at work, Amy was sent away to rehab, returning with an insufferably self-righteous attitude that annoyed everyone around her. Laura Dern’s performance as Amy was one of the very best of the decade, and amid all the cringe-worthy moments, Amy also had a few serene moments of clarity that were genuinely beautiful, no matter how fleeting. She was flawed, but she was trying… and we can all relate to that.
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Rust Cohle, True Detective
Image Credit: Courtesy of HBO The words “time is a flat circle” likely pop into your head first when you see Rust’s name — and for good reason! Of the detective’s many Season 1 monologues, his Episode 5 argument that “this is a world where nothing is solved” was among his most poignant and passionately delivered. But Rust wasn’t just a loquacious kook, as his partner Marty Hart often suspected. He was an intelligent, acutely observant investigator whose worldview was colored by tremendous personal loss, and Matthew McConaughey wore Rust’s weariness like an invisible cloak in his profound, Emmy-nominated performance.
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Arabella Essiedu, I May Destroy You
Image Credit: Courtesy of HBO The title of 2020 Performer of the Year Michaela Coel’s ice-pick-sharp dramedy could well have doubled as a warning to viewers from her complicated protagonist, an author who lived the way that she wrote: without an outline. Arabella was such an effervescent train wreck that she often gave us a contact high through the screen. But she was also possessed of a depth that made the revelation that she’d been raped all the more disturbing and the closure that she was ultimately able to achieve all the more galvanizing.
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Roman Roy, Succession
Image Credit: Courtesy of HBO Look at that smirk! Perhaps the most devious and amoral member of the Roy family — and that’s truly saying something — this brazenly ambitious corporate titan, played with impish glee by Kieran Culkin, revels in his upper-crust status, giggling at the less fortunate and mocking anyone who dares to display an authentic human emotion. (He’s so funny, though, that we can’t bring ourselves to hate him.) We have seen a few small cracks in his emotional armor, thanks to his strange fixation on Gerri and his deep need for Logan’s approval, but mostly, he’s a walking insult machine… and we kind of love him for it.
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Nora Durst, The Leftovers
Image Credit: Courtesy of HBO Over the course of the sublime supernatural drama’s three-season run, TVLine’s 2017 Performer of the Year Carrie Coon evolved her alter ego from a portrait of debilitating grief to one of thrilling resilience. The only resident of small-town Mapleton who lost her entire family in a Rapture-like event called the Sudden Departure, Nora — with time as well as through a complicated relationship with Justin Theroux’s Kevin Garvey — found the courage, maybe the madness, that it took to stop mourning the life that had been so cruelly put behind her and start celebrating the one that lay before her.
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Carmela Soprano, The Sopranos
Image Credit: Courtesy of HBO On an average crime drama, Tony’s wife Carmela would be an afterthought: a nagging downer who merely serves as an obstacle to her husband’s criminal enterprise. But The Sopranos was anything but average, and Carmela — as richly embodied by Edie Falco — was anything but a typical mob wife. She knew full well what Tony was up to, even though it left her wracked with guilt, and despite being hurt by Tony’s brazen infidelities, Carmela entertained a number of dalliances herself, including with Tony’s own bodyguard Furio. Falco and creator David Chase combined to weave a fascinatingly complex portrait of a woman who did her best with an impossible situation and who gave just as good as she got.
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Rue Bennett, Euphoria
Image Credit: Courtesy of HBO Rue knows drugs are bad for her. But she does them anyway, and her constant struggle to stay clean on HBO’s scorchingly intense teen drama is maybe the most harrowing depiction of drug addiction we’ve ever seen on TV. Rue is far from perfect — she lies, cheats and steals to get her latest fix, leaving her family and friends devastated — and it’s frustrating to watch her backslide. But she is trying, and her soul-baring narration and Zendaya’s haunting portrayal keep us on her side, even if we know she’s bound to slip up again and again. (Her love for Jules also gave us a glimmer of hope amid Rue’s usual numbed-up drug haze.) Euphoria can be a tough watch at times, but Rue’s search for inner peace without chemical enhancement makes it all worthwhile.
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Stringer Bell, The Wire
Image Credit: Courtesy of HBO Second in command to drug kingpin Avon Barksdale, Stringer Bell was the true brains behind the operation. His well-thought-out approach to the business served the organization well, but that doesn’t mean he couldn’t be cutthroat when it was called for. But despite being one of Baltimore’s “bad” guys (let’s be real — The Wire was anything but black and white), actor Idris Elba’s performance always had us rooting for him.
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Cersei Lannister, Game of Thrones
Image Credit: Courtesy of HBO Villains don’t come much more appealing than the stunning, savage Lannister daughter, who loved her children fiercely… and rained torture and hardship on pretty much everyone else. Whether you adored her deadly scheming or reveled in her “Shame! Shame! Shame!,” you have to admit: Lena Headey’s character had style.
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Angela/Sister Night, Watchmen
Image Credit: Courtesy of HBO The cop/mom Regina King played was a badass both in and out of her Sister Night guise. Angela’s grounded nature, which more often than not served to remind us that life among superheroes isn’t all it’s cracked up to be, lent the comic adaption a healthy sense of balance. And whenever she’d put on Sister Night’s habit? Well, those fight sequences were pretty awesome, too.
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Kendall Roy, Succession
Image Credit: Courtesy of HBO Kendall should be a happy guy: He’s the heir apparent to his father Logan’s multi-billion dollar global conglomerate Waystar Royco. But money can’t buy happiness, and Kendall is a truly tortured soul, pining for his dad’s approval while burying his anxieties in corporate boasting and drug-fueled partying. As the seasons have worn on, Kendall has tried to stand up to his dad, but he keeps getting beat up like a punching bag, with Emmy winner Jeremy Strong wearing the years of psychological abuse on his face for all to see. It’s the hint of regret and self-recrimination in Kendall’s spirit that makes him more than just another Roy foot soldier — and the most complex character a great show like Succession has to offer.
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Valerie Cherish, The Comeback
Image Credit: Courtesy of HBO While most people look at Lisa Kudrow and immediately think of her Friends persona, true heads see Valerie Cherish, the irreverent, self-absorbed and above all delightful actress whose titular comeback was documented in a short-lived mockumentary. The plight of a washed-up actress may not be uncharted territory, but Kudrow elevated the archetype with every awkward glance, every desperate effort to steer the narrative and, of course, every “I don’t need to see that!” Kudrow earned two Emmy nominations, one for the show’s original 2006 season and one for its 2015 revival — and if we had our way, she would have said, “Well, I got it!” to at least one of them.
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Larry David, Curb Your Enthusiasm
Image Credit: Courtesy of HBO There’s absolutely no one on TV like the lovable curmudgeon that is Larry David. This fictional version of the Seinfeld co-creator never hesitates to go toe-to-toe with peculiar servers, egotistical actors, people who sample too many ice cream flavors and more. In fact, his general disdain for human interaction earned him the moniker of “the social assassin.” It’s always Larry vs. the world, yet despite his generally undiscerning behavior and grumpy mood swings, we can’t help but love the guy.
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Selina Meyer, Veep
Image Credit: Courtesy of HBO There are literally no words we could write that would do justice to the morally bankrupt politician that Julia Louis-Dreyfus so brilliantly played across seven Emmy-winning seasons, but we’ll try. President Meyer was petty, profane, emotionally abusive… she was unlike any political leader we’d ever seen. (Well, at least for those first few seasons.) We were constantly amazed to see someone reach so low and go so high, but we relished every moment of her time in office and miss her administration to this day.
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Tyrion Lannister, Game of Thrones
Image Credit: Courtesy of HBO “I drink, and I know things,” Jaime and Cersei Lannister’s younger brother famously said. But Tyrion did far more than that during the show’s eight-season run. The character (played by Peter Dinklage) was an unlikely warrior, a master strategist, a fool for love, a betrayed believer and — yes — an eminently quotable, jovial drunk.
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Al Swearengen, Deadwood
Image Credit: Courtesy of HBO Fitting for the man who owned the Gem, Ian McShane’s Al was the crown jewel of HBO’s brilliantly crafted Western from David Milch. If he cottoned to ya, Al was a friend to the end (or at least until you gave him cause to look at you sideways). And if you proved to be a foe, there’s no worse enemy you could wish on yourself. Al was mercurial and foul-mouthed and prone to malevolence, yet he was equally crafty — and he also had a well-hidden soft spot for the likes of Trixie. He was, simply, the man that brought Deadwood to life.
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Samantha Jones, Sex and the City
Image Credit: Courtesy of HBO Carrie Bradshaw may have been the leading lady of HBO’s fabulously raunchy rom-com, but Samantha was undeniably the one who put the “Sex” in the title. Samantha’s sexually voracious lifestyle — she was “sex-positive” before that was even a thing, honey — was the engine that provided SATC with its trademark tawdry humor, along with her winking double-entendres. She gave Kim Cattrall an instantly iconic, career-defining role, and her proudly promiscuous ways gave the other ladies (along with millions of viewers) permission to lose their own inhibitions. Plus, aside from all the hookups, she was a fiercely loyal friend to Carrie and company and a damn good businesswoman to boot. Samantha’s relentless quest for sexual pleasure established HBO as a bold boundary-pusher in the world of television — and to this day, she exemplifies HBO comedy at its very pinnacle.
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Omar Little, The Wire
Image Credit: Courtesy of HBO Nothing sparked fear in the streets more than these simple words: “Omar’s coming!” West Baltimore’s most infamous stick-up man tussled with both the Barkdale and Stanfield organizations, while sporting a trench coat and a shotgun, making him the show’s most iconic (and identifiable) figure. Plus, he’s easily one of the most intriguing openly gay characters in TV history, a man whose ruthlessness was balanced by his complex sense of righteousness.
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Tony Soprano, The Sopranos
Image Credit: Courtesy of HBO C’mon, was there really any other choice for the top spot here? Fuhgeddaboudit. A hotheaded mob boss with serious anxiety issues, Tony was a study in contradictions, with a soft side that won us over — and a violent temper that reminded us just how dangerous he could be. He was thoughtful, he was stubborn, he was playful, he was cruel… the sheer complexity and nuance that went into Tony’s persona was like that of a classic novel, pioneering the concept that we didn’t have to condone a character’s behavior to be utterly riveted while watching him. (It helped, of course, that James Gandolfini delivered perhaps the single greatest performance in television history.) Tony started out the series pining for the days of heroes like Gary Cooper, but he turned out to be the complicated anti-hero that ushered in a new era for the small screen, with his distinctive DNA infused into everyone from Don Draper to Walter White. For HBO, though, he was a true hero, announcing the network as a programming powerhouse and still standing as the most enduring testament to its incredible legacy.
