Unsung Heroes: HBO’s 25 Best Supporting Characters

No network has a more prestigious resume than HBO. Over more than 50 years in business, Home Box Office has defended its title of Heavyweight Champion of the Television World again and again, and it has done so by creating the most believable, compelling characters fathomable. These legendary side characters capture what HBO is all about.

1. Al Swearengen: Deadwood

In a South Dakota mining town that hosted the likes of Calamity Jane and Wild Bill Hickok, fire-tongued bartender Al Swearengen may have been the most intimidating of the lot. English actor Ian McShane is an accomplished performer, but this will almost certainly be the role that defines his career.

2. Tyrion Lannister: Game of Thrones

Tyrion Lannister’s mischievous Machiavellianism and voluminous vocabulary immediately earned fans’ lasting adoration in a show that was the sum of its supporting actors (many of whom you might argue were really main characters).

3. Paulie Gualtieri: The Sopranos

Paulie Walnuts was the mafioso of using the wrong word in the wrong situation. Though undeniably a gangster, Walnuts also accounted for a hefty portion of The Sopranos‘ comic relief.

“Word to the wise: Remember Pearl Harbor!”

4. Jimmy McNulty: The Wire

If you did not know that actor Dominic West was born in Sheffield, England, you’d have sworn he was a child of Charm City. His turn as self-centered, workaholic (and alcoholic) Baltimore detective Jimmy McNulty remains the gold standard for dysfunctional police archetypes.

5. Ari Gold: Entourage

A little bit of Ari Gold goes a long way. Fortunately, Entourage showrunner Doug Ellin sprinkled Jeremy Piven’s Gold (reportedly inspired by real-life superagent Ari Emanuel) throughout the show. If Ari was to give a Ted Talk, it might be aptly titled “The Art of the Expletive.”

6. Omar Little: The Wire

The phrase “you come at the king, you best not miss” remains one of the seminal quotes of television’s Golden Era. The warning was one of many memorable quotes uttered by street poet Omar Little, The Wire‘s lone wolf who made hardened criminals look like mere sheep.

7. Logan Roy: Succession

A giant of HBO’s 2020s catalog, Logan Roy was presumably the caricature of real-life media mogul Rupert Murdoch. However, thanks to Brian’s at-times menacing (and, at times, pathetic) portrayal of the patriarchal billionaire, Logan Roy transcended whatever source material he originated from.

8. Junior Soprano: The Sopranos

In Junior’s words, his nephew Tony “never had the makings of a varsity athlete.” However, there is no debate that Junior’s biting one-liners, caramel-sweet ways with the ladies, and ultimate descent into paranoia make him one of HBO’s most memorable side characters.

9. Calamity Jane: Deadwood

Deadwood is a show that thrives on a deep roster of characters who play off each other’s controlled mania. Robin Weigart’s Calamity Jane is one of the sparks in the powderkeg that is Deadwood, South Dakota. She is a foul-mouthed, soot-faced cowgirl who never hesitates to pull her side piece when she senses a perceived slight, which makes her a bonafide scene stealer.

10. Ramsay Bolton: Game of Thrones

If the never-ending stream of true crime documentaries proves anything, it’s that Americans are fascinated by society’s sadists. It’s no surprise that Game of Thrones’  Ramsay Bolton is one of the show’s most memorable personalities. Stigmatized by his status as a love child, Bolton took his inner angst out on others, leaving fans to wonder: When will this guy’s karmic comeuppance finally come?

11. Stringer Bell: The Wire

An aspirational figure for those raised in the streets, Stringer Bell, was the CEO of The Wire‘s vaunted Barksdale Crew. Yet, despite ruling with a Rolex-clad first throughout the show’s early season, Stringer’s ambition to go legit would precipitate his downfall.

A walking, breathing, Coogi-wearing testament to staying in your lane, Stringer Bell is just as much a cautionary tale as a television character.

12. Leon Black: Curb Your Enthusiasm

Leon Black brought out a side of Larry David that many viewers didn’t know Larry had. From bestowing the nickname “Long Ball Larry” to dropping knowledge such as “You can’t pause toast, Larry. It loses its essence!”, Leon Black was the Five Hour Energy in Curb Your Enthusiasm‘s later seasons.

13. Titus Pullo: Rome

One of HBO’s  most underappreciated shows, Rome, focused heavily on the relationship between Roman soldiers Lucius Vorenus and Titus Pullo. The lower-ranking brute in the partnership, Pullo brought charisma, brawn, and brute strength to a show that faithfully depicted the good, bad, and ugly of the Roman Empire.

14. Ralph Cifaretto: The Sopranos

Truthfully, we couldn’t be faulted if half of this list were characters from The Sopranos not named Tony. Yet, Ralph Cifaretto manages to make the shortlist.

Equal parts charming, revolting, and sadistic, Cifaretto suffers perhaps the most memorable demises in a show littered with memorable demises.

15. Erlich Bachman: Silicon Valley

Mike Judge’s Silicon Valley carved a lane of its own on HBO as an irreverent ensemble comedy heavy on tech jargon. T.J. Miller’s Erlich Bachman became the poster boy of this R-rated response to The Big Bang Theory, though the actor’s off-screen antics ultimately became too much for Judge and his crew to tolerate.

16. Gyp Rosetti: Boardwalk Empire

Bobby Cannavale cemented his status as a hulking, limelight-hogging (in a good way) dynamo of an actor through his role as volatile gangster Gyp Rosetti in Boardwalk Empire. Seemingly a man’s man, Rosetti had mommy issues and an explosive temper, making him a must-watch character in one of HBO’s best shows.

17. Johnny Drama: Entourage

Johnny Drama was the funniest element of Entourage, and it wasn’t particularly close. Actor Kevin Dillon played Johnny Chase, the less-accomplished older brother of acting superstar Vinnie Chase. Dillon was working from experience, as his real-life brother Matt Dillon has had far more success in Hollywood than he.

18. NoHo Hank: Barry

Barry‘s final season left many viewers puzzled and disappointed. By and large, though, Barry was a smashing success, and Anthony Carrigna’s NoHo Hank perfectly captured Barry‘s off-the-wall tone.

When you’re creating a comedy show about a hitman, you need characters with a similarly bi-polar aura. NoHo Hank was just that.

19. Vernon Schillinger: Oz

Premiering in July 1997, Oz was one of the shows that put HBO on the map as a gritty, no-limits alternative to censored network television. J.K. Simmons’ Vernon Schillinger was the menacing leader of the Aryan Brotherhood’s presence in the Oswald State Penitentiary.

With his booming baritone and unhinged grin, Simmons is an actor who always commands your attention.

20. Erroll Childress: True Detective

After following a winding, unnerving path to the end of True Detective’s first season, viewers are confronted by Glenn Fleshler’s Errol Childress. Living in a remote shack in Erath, Louisiana, Childress proves to be the worthy monster that Woody Harrelson’s Marty Hart and Matthew McConaughey’s Rust Cohle have been pursuing.

21. John Stone: The Night Of

The Night Of is in the discussion of HBO’s most underrated shows, and John Turturro’s John Stone plays a substantial role in this hyper-authentic examination of New York City’s criminal justice system. Stone is a criminal defense lawyer with a debilitating skin rash.

Writers Richard Price and Steven Zaillian use Stone as Exhibit A in their masterclass of “Character Development 101.”

22. Tanya McQuoid: White Lotus

Jennifer Coolidge is an actress whose mere appearance makes you chuckle but who never quite owned a starring role in any film or TV show. White Lotus proved that Coolidge could carry a role throughout an entire season of television, sticking to her usual brainless schtick and succumbing to one of the most hilarious television passings ever scripted.

23. Johnny Burns: Deadwood

Far from a lead character, barkeep and invalid Johnny Burns serves as the resident punching bag at Al Swearengen’s Gem Saloon. In a show that has far more comic relief than you might expect, Burns’ character is one of the most reliable sources of levity.

24. Captain Herbert Sobel: Band of Brothers

Because Captain Herbert Sobel was a real person who served as a commissioned officer in the U.S. Army during World War II, he certainly deserves respect. However, Band of Brothers portrays Sobel in such a poor light that it’s impossible to forget his unrivaled arrogance and futile brand of leadership.

25. Stevie Janowski: Eastbound and Down

The clueless sidekick to Danny McBride’s Kenny Powers, Stevie Janowski, is the definition of a “ride or die.” Fortunately for viewers, Powers never leads the dimwitted sycophant, Janowski, into any fatal quandaries. Which, fortunately for us, means we get to enjoy the “ride.”