The Ten Funniest Recurring Characters Currently on TV

All good comedies have a main cast of memorable characters, but the great ones expand their worlds to include all sorts of other characters, ones that stop by only once in a while. The Simpsons is most famous for this, with the city of Springfield populated by dozens of memorable ancillary characters, but it’s far from alone. Below, we’ve compiled a list of what we feel are the 10 finest examples of recurring characters from today’s sitcoms. And yes, we kept it to one per show just so this isn’t a rundown of 10 Simpsons characters.

Dennis Duffy (played by Dean Winters) — 30 Rock

Liz Lemon’s ex-boyfriend Dennis Duffy, the Beeper King, has become 30 Rock’s equivalent to Sideshow Bob. While he’s not trying to kill Liz Lemon, a la Bob and Bart, he emerges on the show annually with a new evil scheme that’s pathetic instead of dangerous. Actor Dean Winters really nails this sleazy, doltish character, and Dennis’s oft-illegal antics are always a great source of amusement. Over the years, Dennis has been baited by To Catch a Predator, attempted to recreate the balloon boy hoax with a child left in his care through a big brother program, and tried to get Liz to allow him to move back in with her while she was delirious from a gas leak. But his most morally astounding accomplishment is trying to push Liz in front of a speeding subway car only so he could save her and retain his status as a “Subway Hero,” after having previously saved someone from a similar fate. Dennis Duffy is a character who would be right at home with the sociopaths on It’s Always Sunny in Philadelphia; but by placing him in 30 Rock’s world, where everyone is not like him, the character stands out and is much more entertaining.

The Captain (played by Kyle MacLachlan) — How I Met Your Mother

I think most How I Met fans would agree that Ted’s love interest of season six, Zooey, was a pretty unlikable character (or pretty, unlikable character, if you prefer). She felt like a season-long stall, because obviously she wasn’t going to be the titular mother. But there was one great thing she brought to the show: her husband, The Captain, played by Agent Cooper himself. He only appeared in three episodes, but each one was instantly memorable: his introduction in “Natural History Museum”; Marshall noticing in “The Mermaid Theory” that the top half of the Captain’s face is cheerful, but the bottom half wants to “murder you”; and Ted and The Captain, sitting in the latter’s study, drinking some “damn good brandy” in “Garbage Island.” I doubt he’ll return to the show, but putting up with Zoe for one more episode would be worth it if The Captain tagged along.

Milhouse Van Houten (voiced by Pamela Hayden) — The Simpsons

There are literally hundreds of characters to choose from here. Really, my decision came down to looking over Wikipedia’s list of recurring characters on The Simpsons and whichever name made me laugh the loudest, that’s who I was going to pick. Originally, I was going to go with Hans Moleman, then Lionel Hutz, but my final choice is: Milhouse Van Houten. So many of my favorite moments on my favorite show are Thrill HO(use)-related, like “Remember ALF? Well, he’s back…in pog form!” and, after Lisa says he’s like a big sister, the bespectacled bluehead responds, “No, I’m not! Why does everyone keep saying that?” Everything is, finally, coming up Milhouse.

Rickety Cricket (played by David Hornsby) — It’s Always Sunny in Philadelphia

Perhaps the person hurt most by the Gang’s sociopathic schemes on It’s Always Sunny, Matthew “Rickety Cricket” Mara has seen his quality of life take a drastic downturn with each run-in with the staff of Paddy’s Pub. Played by long-time writer for the show David Hornsby, Rickety Cricket usually pops up just once each season, but it’s always worth waiting for to see how the Gang will screw him over next. In one of the show’s best running jokes, Dennis, Dee, Charlie, Mac, and Frank inadvertently harm Cricket in a major way each time he pops into their lives. When we first met him, he was a God-fearing priest who was unfortunate enough to have gone to school with the show’s central characters. Over the course of six seasons, the Gang has been responsible for him being kicked out of the priesthood, becoming a homeless crack addict, and having his legs broken by the mob. Dennis and Mac even hunted Cricket for sport, and Frank slashed his throat with rusty garbage can lids. Who knows what fate the show’s upcoming seventh season will bring for Rickety Cricket? At this point, it’s amazing he’s still breathing.

Zapp Brannigan (voiced by Billy West) — Futurama

The world, or at least the Internet, should have exploded with nerdy excitement when Zapp Brannigan, captain of the Nimbus, met James T. Kirk, captain of the Enterprise, in “Where No Fan Has Gone Before,” Futurama’s Star Trek (or is that Star Trek Wars or Star Wars Trek?) parody. Brannigan is obviously based on Kirk, but at least the man they called Tiberius was a good captain; Brannigan, on the other hand, got kicked out of DOOP for attacking the harmless Neutral Planet (motto: “Live Free or Don’t”). He’s arrogant, a liar, gets naked way too often, doesn’t understand metaphors (“If we hit that bull’s-eye, the rest of the dominoes should fall like a house of cards. Checkmate.”), and disregards his self-proclaimed Brannigan’s Law. And that’s precisely why he’s our favorite scene-stealer from the 31st Century.

Leon Black (played by JB Smoove) — Curb Your Enthusiasm

When Larry David’s wife, Cheryl, guilted him into taking in a family of hurricane refugees at the start of the show’s sixth season, I was a bit underwhelmed with the first episode to feature the oh-so-subtly named family, the Blacks. Any apprehensions I had about the season’s story arc was washed away as if by a giant storm when the Black family uncle, Leon (played by stand-up and ex-SNL writer JB Smoove) presumptuously moved into Larry David’s house. Leon wasn’t displaced by the hurricane; he’d been living in L.A. already and jumped at the chance to live for free in the mansion of a rich TV producer. Over the course of the next two seasons, Larry and Leon became a sure-fire comedy team, with Larry playing the straight man on the receiving end of Leon’s irrational advice and opinions. Curb fans will be delighted to hear Leon is returning for season eight this summer, so we have plenty of ruckus-bringing to look forward to. Leon’s best moment has to be impersonating Larry’s deceased friend, Danny Duberstein, to convince Seinfeld star Michael Richards that a disease he has is nothing to worry about. Richards chew out Leon when he discovers the ruse, but it’s in front of a long line of tourists who videotape what looks like another racially motivated outburst from Michael Richards. It was the perfect chance to address Michael Richards’s recent troubles in a funny and new way and a great showcase for JB Smoove’s rapid-fire comic abilities.

Jean-Ralphio (played by Ben Schwartz) — Parks and Recreation

Our feelings for Jean-Ralphio, as well as how the man possesses such unique rapping abilities, can be found here, but let me add: Michael Schur and the writers of Parks and Recreation are aware that there’s too much of a good thing, particularly when it relates to smaller-scale characters. We don’t need to know every little thing about, say, Perd because the less we know, the funnier the character is (this is a common criticism of later-day Simpsons episodes, where we now know the entire history of the Crazy Cat Lady). We only see Jean-Ralphio when he’s in the office, with Tom, or at the Snake Hole, with Tom, or at a funeral for Lil’ Sebastian, with Tom, and the little we know about his personal life is that he works at Lady Foot Locker (part-time now, with the expansion of Entertainment 720). It’s fun imagining what Jean-Ralphio does off-screen, and that’s part of his charm. That, and every line he speaks is golden.

Frank (played by Todd Giebenhain) — Raising Hope

It’s fun watching a show in its first season trying to figure out what works and what doesn’t. The writers of Raising Hope realized quickly that their main character, Jimmy, isn’t very funny, so they’ve decreased his screen time and increased it for the people around him, like his parents, Virginia and Jimmy, and his Howdy’s East co-worker, Frank. He’s the kind of guy who doesn’t need a last name and describes himself as a “Pisces…born in the Year of the Rat.” Simply put, he’s weird, wonderfully so, and his one-liners (when told that he and his fellow employees should consider themselves “individuals working within a larger framework,” he replies, “Like Al Qaeda?”) have already become the show’s best joke.

Magnitude (played by Luke Youngblood) — Community

Introduced just this past season, Magnitude, the Greendale student who’s known for frequently belting out his inane catchphrase “Pop-pop!”, is well on his way to becoming a national phenomenon. Magnitude already received this much-needed oral history profile on The Wrap, but that piece only scratches the surface. Magnitude is intentionally shallow, a commentary on introducing a faulty new character into an established show. His catchphrase — so simple and meaningless — satirizes the concept of a catchphrase, much in the same way Ken Marino’s “I Wanna Dip My Balls In It” character on The State did. Magnitude is just part of the excellent roster of supporting characters Community has built over the course of two seasons, and I’m sure we’ll all be seeing plenty of him in the future.

Randy Marsh (voiced by Trey Parker) — South Park

Stan Marsh’s father, Randy, has been around since South Park’s first season, but it took Matt Parker and Trey Stone a few years to figure out just how effective it could be to show Randy’s wild side. Beneath Randy’s calm and normal exterior lies an emotionally flighty manchild who’s prone to grow intensely obsessed over the most insignificant things. Whether it’s trying to be the drunkest father in the stands at Stan’s Little League games or competing with Bono to take the world’s biggest dump, Randy Marsh is always entertaining when Parker and Stone put him front and center. It took them a few seasons to discover the depths to which they could take this character, but Randy’s become a dependable source of comedy in recent years.

Josh Kurp is East Coast, Bradford Evans is West Coast.

The Ten Funniest Recurring Characters Currently on TV