Top 10 Hilarious Recurring Characters from Sitcoms
#10: Steven William Upshaw [aka “Crazy” Steve]
“Drake & Josh” (2004-07)
Every time this mentally impaired movie theater employee encountered Drake and Josh, a freakout was inevitable. We never knew what would set Crazy Steve off, though. Whether it was a complaint about a cupholder or not being able to watch “Dora the Explorer,” Steve had a tendency to lose it over the most minor things. Part of what makes Steve so hilarious is that he remains something of an enigma. It’s unclear why Steve is full of rage or why Mondays are particularly bad days for him. We’re not sure what became of Crazy Steve after the series ended, although we heard a rumor that changed his name to Spencer, kidnapped Megan, and moved to Seattle. That’s so crazy that it actually makes perfect sense.
#9: Jazz
“The Fresh Prince of Bel-Air” (1990-96)
Before Will Smith broke out as an actor, he regularly collaborated with DJ Jazzy Jeff. Even after Smith got his own sitcom, his music partner still occasionally dropped by the Banks mansion as the Fresh Prince’s best friend. Jazz was responsible for some of the show’s funniest running gags, most notably getting thrown out of the house by Uncle Phil. This was oftentimes prompted by Jazz’s habit of saying the wrong thing at the wrong time, as well as his unrequited crush on Hilary. When Jazz wasn’t getting tossed out, he was usually going along with one of Will’s schemes or doing something sketchy all on his own. Being anything but civilized, Jazz was an always welcome wrench in the Banks family’s high-class lifestyle.
#8: Beverley Leslie
“Will & Grace” (1998-2006; 2017-20)
Well, well, well! Much like his arch-frenemy, Karen Walker, Beverley Leslie is lovable despite his despicable actions. Where Karen has something resembling a shriveled up conscience, though, Beverley seems content with being an all-around shallow and hypocritical socialite. It takes a dose of morphine for Beverly to finally open up about his sexuality and even then, he doesn’t stay out of the closet for long. Of course, Karen and Beverley are on the same playing field when it comes to insults. For every shot Karen takes at his size and sexuality, Beverley has an equally snarky one-liner about her demons. The role won Leslie Jordan a Primetime Emmy for Outstanding Guest Actor in a Comedy Series, cementing Beverley’s legacy as a fan favorite.
#7: Matthew Mara [aka Rickety Cricket]
“It’s Always Sunny in Philadelphia” (2005-)
It’s a good thing that Cricket is only a recurring character because we’re not sure how much more torment this guy can possibly handle. After surviving high school with the gang, Cricket gets his life together as a priest. Cricket leaves the priesthood for a shot with Dee, only to get his heart broken. Now homeless, Cricket’s life spirals into a never-ending cycle of desperation and debauchery. Watching all the Cricket-centric episodes in order, you’ll notice a hilariously depressing devolution with each of his appearances. Every time it seems like Cricket has endured the worst, he’s shot at, severely burned, or forced to do something unbelievably degrading. “It’s Always Sunny” is showing no signs of slowing down, which means Cricket’s misery is far from over.
#6: Barry Zuckerkorn
“Arrested Development” (2003-06; 2013-19)
He may not be as iconic as the Fonz, but Barry Zuckerkorn is sure to go down as one of Henry Winkler’s most outrageous characters. If a lawyer can’t remember to take the foil off a Ding Dong before putting it in the microwave, chances are that he’s not the best person to provide legal advice. The Bluth family learns this the hard way time after time. Despite being an attorney, Barry’s incompetence usually gets him on the wrong side of the law, whether he’s accidentally running over Tobias or picking up a lady who works two jobs. Of course, Barry isn’t without his redeeming qualities. After all, it takes a keen eye to tell the difference between an actual landscape and Tobias’ “landscape.”
#5: Charlotte Harris
“Victorious” (2010-13)
Better known as André’s grandmother, Charlotte is about as stable as Crazy Steve, albeit for different reasons. Where Steve has a serious anger management issue, André’s grandmother possesses an irrational fear of ceiling fans, the shower… you know what? There’s not enough time to list all of her phobias, so let’s just say everything! When André’s grandmother confronts her fear of leaving the house, nobody is safe from her erratic behavior or loud voice. Again, it was probably wise to limit Andre’s grandma to a recurring role because if she were a regular player, our eardrums might’ve exploded. Fortunately, “Victorious” knew exactly how much of this over-the-top character to give us. Every time we heard her shout, “André,” we immediately started screaming with laughter.
#4: Jean-Ralphio Saperstein
“Parks and Recreation” (2009-15)
He might not have been a mainstay of Pawnee’s Parks Department, but Jean-Ralphio helped launch comedian Ben Schwartz into mainstream popularity. As a matter of fact, this eccentric character was specifically written with Schwartz in mind. Sporting a ridiculous hairdo and infamous for singing into other people’s ears, it’d be an understatement to say that Jean-Ralphio is extra. With deep pockets and little common sense, Jean-Ralphio is typically onboard for whatever business venture Tom Haverford cooks up. It’s a good thing that Jean-Ralphio is “flush[ed] with cash” because his work ethic is virtually nonexistent and he’s not as good with people as he thinks he is. Donna may “hate that guy,” but we can’t help but love him.
#3: Doug Judy
“Brooklyn Nine-Nine” (2013-)
Jake Peralta’s relationship with Doug Judy is hard to put a label on. With one being a cop and the other being the Pontiac Bandit, Jake initially views Judy as his arch-enemy. Regardless, Jake simply can’t resist Judy’s laidback charm, no matter how many times he betrays his trust. In spite of all the backstabbing and carjacking, we have to admit that Judy seems like a cool guy to hang out with. Even when he’s under arrest, the guy is so chill about it. While Judy does earn Jake’s friendship in later seasons, he constantly finds new ways to catch the 99 and the audience off guard. Jake should make a less unpredictable friend… like Adrian Pimento! Err, on second thought, just stick to Charles.
#2: Janice Litman-Goralnik
“Friends” (1994-2004)
With a nasally catchphrase and cackle, Janice secured her place as one of television’s most unforgettable recurring characters. If only Chandler and his friends could forget about Janice. Whenever it seemed like they’d seen the last of her, Janice resurfaced to stir up more annoyance. Although Chandler spent almost ten years trying to shake off Janice, her presence was always a treat for the audience. Since Janice popped up at least once per season, it was fun trying to guess how she’d reenter the gang’s lives. Sometimes it was for an extended period, other times it was just briefly, and most of the time it was at the worst possible moment. In any case, nothing could ever prepare the viewer for those familiar three words.
Before we unveil our top pick, here are a few honorable mentions.
Dr. Leo Spaceman, “30 Rock” (2006-13)
Are We Sure This Guy Is a Doctor… Or Even Human?
The Judge [aka Judge Gen], “The Good Place” (2016-20)
We’d Love to Take a Look At Her TV Watchlist
The Captain, “How I Met Your Mother” (2005-14)
Kyle MacLachlan at His Creepiest, Which Is Saying Something
Alex "Star-Burns" Osbourne, “Community” (2009-15)
His Nickname Alone Is Brilliant
Reverend Richard Wayne Gary Wayne, “Unbreakable Kimmy Schmidt” (2015-19)
Just Don’t Get Into His Van or Bunker
#1: Newman
“Seinfeld” (1989-98)
While it was tempting to highlight Jerry Stiller’s Emmy-nominated role as Frank Costanza, no recurring character on “Seinfeld” had a stronger presence than Newman. Originally, Newman was an off-screen role with Larry David providing his voice. When Wayne Knight was cast in a later episode, though, the creators went back and replaced David’s voice with his. It was a good call because Knight lives and breathes this U.S. Postal worker. Neman is to Jerry what Lex Luthor is to Superman. Part of what makes Newman’s diabolical nature so funny is that he’s really just a sniveling dweeb with no power. Whenever Newman can make Jerry’s life inconvenient, though, he relishes in it like a supervillain. Despising a sitcom character has never been more fun.